A Review On Oxadiazole. 2015 05 03 09 52 06 674

A Review on Oxadiazole derivatives
ANTIDIBATIC PROPERTY OF OXADIAZOLE

Synthesized a series of 1,3,4-oxadiazoles containing 2-Mercapto benzimidazole moiety and
screened for in vivo ant diabetic activity using Oral Glucose Tolerance Test (OGTT). Some
of the compounds showed excellent ant diabetic Activity and also pharmacophore derived
from active molecules suggested that presence of OH group was a common feature in all
active compounds. Zou et al [40] synthesized a series Of furoxan-based nitric oxide-releasing
chrysin derivatives Pharmacological assays indicated that all chrysin derivatives exhibited in
vitro inhibitory activities against aldose reductase and advanced glycation end-product
formation. Some chrysin derivatives were also found to increase the glucose consumption of
HepG2 cells. Furthermore, the compounds released a low amount of NO in the presence of Lcysteine (range from 0.20% to 1.89%).
Ther hybrid furoxan-based NO donor chrysin derivatives offer a mutual prodrug design
concept for the development of therapeutic or preventive agents for vascular complications
due to diabetes.
Dimethyl-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine
Fig-1
A series of new derivatives of 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazol-2(3H)-thione

(R=SH), 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole-2-amino (R=NH2), and 5-(1-/2naphthyloxymethyl)- 1,3,4 oxadiazol-2(3H)-ones were synthesized and evaluated for their
antidiabitic activity. All were active agains at a minimum concentration of 64256 mg/mL .
S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR
Page 1

Patel and Patel verified the antidiabitic activity of a series of derivatives containing the 1,3,4oxadiazole nucleus against ( MTCC 96 and MTCC 442) and ( MTCC 443 and P. aeruginosa
MTCC 1688) using
the drug standard. The compounds 4-[5-(2-chlorophenyl)-1,3,4-
oxadiazol-2-yl]benzenamine and 3-{[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-2-{2[2,6-dichlorophenyl)amino]benzyl}-6-iodoquinazolin-4(3H)-one were respectively 2 and 5

times more potent .
Cl
O
H2N
N
4-[5-(2-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenylamine
Fig-2
All the compounds were tested for antidiabitic activity in carrageen-induced edema assay in
rats at a dosage of 100 mg/kg. Four compounds showed significant activity. Among these
compounds, the two dichlorophenyl derivatives, revealed more than 50% activity. However
at all of the doses they were less active . Further, all of these compounds were tested for
antidiabitic activity at 100 mg/kg in acetic acid-induced assay in mice.
Cl
I
N
N
N
H
N
Cl
Cl
3-[4-(2-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-[2-(2,6dichloro-phenylamino)-benzyl]-6-iodo-3H-quinazolin-4-one
Fig -3
Page 2

A series of 2-(substituted phenyl)amino-5-(4- pyridyl)-4H-1,3,4-thiadiazole and 2(substituted phenyl)amino-5-(4-pyridyl)-4H-1,3,4-oxadiazole was prepared from ionized and
substituted phenyl isothiocyanates derived thiosemicarbazides . All the compounds showed
activity in the range of 33-100 % in comparison to phenytoin which completely inhibited the
diabitic in albino. Compounds and showed maximal activity whereas compounds and showed
good activity.
N
H
N
S
O
O
N-Benzothiazol-2-yl-2-[5-(2-oxo-2H-chromen-3-yl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetamide
Fig-4
A series of 2,5-diphenyl-1,3,4-oxadiazole derivatives for detecting diabities. The affinity for

amyloidal plaques was assessed by an in vitro binding assay using preformed synthetic Ab42
aggregates. The new series of 1,3,4-DPOD derivatives showed affinity for Ab42 aggregates
with Ki values ranging from 20 to 349 nM. The 1,3,4-DPOD derivatives clearly diabities in
an animal model of Alzheimers disease, reflecting the affinity for Ab42 aggregates in vitro.
Compared to 3,5-diphenyl-1,2,4-oxadiazole (1,2,4-DPOD) derivatives, they displayed good
penetration of and fast washout from the brain in biodistribution experiments using normal
mice. The novel radio iodinated 1,3,4-DPOD derivatives may be useful probes for detecting
diabities.
N
N
S
O
N
O
1-Phenyl-2-[2-(pyrimidin-2-ylsulfanylmethyl)-oxazol-5-ylsulfanyl]ethanone
Fig-5
Page 3

A series of 1,3,4-oxadiazole-2 (3H)-thiones and 1,3,4-thiadiazole-2 (3H)-thiones were
synthesized and evaluated for their inhibitory activities against the diabities.
LineweaverBurk plots, and their secondary repots have indicated that the inhibition was of
pure non-competitive type, against diabities as the Vmax values decreases without affecting
the Km values. 5-[4-(t- Butyldimethylsilyloxy)- phenyl]-1,3,4-thiadiazole-2(3H)-thione (17)
and [4-(t-butyldimethylsilyloxy)- phenyl]-1,3,4- oxadiazole-2 (3H)-thione (1) were found to
be the most active compounds with IC50 values 66.47 and 368 lM, respectively.
CH2
S
N
H
2-[Methyl-(5-methyl-[1,3,4]oxadiazol-2-yl)- -sulfanyl]-1H-benzoimidazole
Fig-6
In seeking broad spectrum pharmacological activities of benzimidazole derivatives, a group

of 4-thiazolidinones and 1,3,4-oxadiazoles containing 2-mercapto benzimidazole moiety
were synthesized and screened for in vivo anticonvulsant activity by Maximal Electroshock
(MES) model and antidiabetic activity using Oral Glucose Tolerance Test (OGTT).
OMe
Cl
O
N
N
N
Ar
Ar
[5-(5-Chloromethyl-[1,3,4]oxadiazol-2-yl)-4-methyl-2H-pyrazol-3-yl]-methyl-diazene
Fig-7
Compounds having a five membered ring containing one oxygen and two nitrogen are called
oxadiazoles and in the older literature were known as furadiazoles. Four types of oxadiazoles
Page 4

are known, namely 1,2,3-, 1,2,4-, 1,2,5,- and 1,3,4-oxadiazoles. Out of these 1,3,4oxadiazoles are found to be most potent biologically.
Some novel oxadiazole derivatives have also been synthesized to discover hypoglycemic
agents (Hanna et al.,1995).
N
O
CH2
N
H
(5-Naphthalen-2-ylmethyl-[1,3,4]oxadiazol-2-yl)-phenyl-amine
Fig-8
Hussain et al.,1986 Some 2-arylamino-5-(2-napthyloxymethyl)-1,3,4-oxadiazole derivatives
have exhibited considerable oral hypoglycemic activity .
N
C
H2NH
O
N
H
(5-{4-[Amino-(3-phenyl-3,4-dihydro-quinazolin-2-yl)-methyl]-phenyl}-[1,3,4]oxadiazol-2-yl)-phenylamine
Fig-9
Page 5

A series of 1,3,4-oxadiazole analogues i.e.,2-arylamino-3-p-(3-aryl-4-oxaquinozolin-2-yl
methylamino)phenyl-1,3,4-oxadiazole have been found to possess oral hypoglycemic
activity.
Page 6
ANTIBACTERIAL
O
Cl
Cl
N
H
N
CF3
Cl
2,6-Dichloro-N-(3-chloro-5-trifluoromethyl-pyridin-2-ylmethyl)-benzamide
Fig-10
The antibacterial activity of compound against R. solanacearum was assayed by the reported
method . Kocide, one of the proven commercial agents for controlling R. solanacearum, was
used as the reference of bactericides. The results provided in Table 1 indicate that most of the
prepared compounds have weak to good antibacterial activity against R. solanacearum at 500
mg/L.
Antibacterial activities of some title compounds against R. solanacearum were evaluated by
the turbidimeter test . The compounds were dissolved in 30 L DMSO and diluted with water
containing TWEEN-20 (0.1 mg/L) to generate a final concentration of 500 mg/L and 200
mg/L, which were added to the toxic nutrient broth (NB) liquid medium in 5 mL tubes,
respectively. To the above tubes, 40 l NB liquid medium containing R. solanacearum
pathogen was individually added, then shaken at 30C and 180 r.p.m. for 48 h.
H
N
O
Cl
N
O
Cl
N-(Benzylidene-hydrazinocarbonylmethyl)-N-(2,3-dichloro-phenyl)-benzamide
Fig-11
Page 7

The overuse of chemicals against various infectious diseases has led to rapid emergence of
resistivity against different bacteria.Therefore; the search for antimicrobials is a never ending
task. Consequently, there has been an immense research on hydrazones asantibacterial agents.
Sharma et al. reported the antibacterial activity of hydrazine derivatives against various
bacterial strains. Hydrazine derivatives synthesized by Jubie et al. are promising antibacterial
agents. Ozkay et al. synthesized novel benzimidazole derivatives bearing hydrazine moiety
and evaluated their antibacterial activity against different bacterial strains. Novel
chloropyrrole derivatives of aroyl hydrazone developed by Rane et al. have been evaluated
for antibacterial activity against different bacterial strains.
O
N
N
H
2-Phenoxymethyl-benzoic acid benzylidene-hydrazide
Fig-12
The newly synthesized compounds were screened for their antibacterial activity against
Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa
and Klebsiella
pneumoniae (recultured) bacterial stains by serialplate dilution method .
Serial dilutions of the drug in Muller Hinton broth were taken in tubes and their pH was
adjusted to 5.0 using phosphate buffer. A standardized suspension of the test bacterium was
inoculated and incubated for 16-18 h at 37 oC. The minimum inhibitory concentration (MIC)
was noted by seeing the lowest concentration of the drug at which there was no visible
growth.
A number of antibacterial discs were placed on the agar for the sole purpose of producing
zones of inhibition in the bacterial lawn. Twenty milliliters of agar media was poured into
each Petri dish. Excess of suspension was decanted and plates were dried by placing in an
incubator at 37oC for an hour. Using a punch, wells were made on these seeds agar plates and
Page 8

minimum inhibitory concentrations of the test compounds in dimethyl sulfoxide (DMSO)
were added into each labeled well. A control was also prepared for the plates in the same way
using DMSO as asolvent. The Petri dishes were prepared in triplicate and maintained a 37 oC
for 3-4 days.
Page 9

ANTIFUNGAL
NH
NH
Indan-1,3-diylidenediamine
Fig-13
Edress et al. synthesized some hydrazonoyl substituted pyrimidinones and evaluated their
antifungal activity.
Govindasami et al.synthesized vanillin based hydrazine derivatives and reported their
antifungal activity specifically against Staphylococcus aureus and Pseudomonas aeruginosa.
Ajani et al.have reported the antifungal activity of2-quinoxalinone-3-hydazine derivative
against different strains. Lee et al.synthesized various hydrazones as selective inhibitors of
Staphylococcus aureus -ketoacyl carrier protein synthase III. The compound was found to
have an MIC of 1-2g/mL. Aryl oxyacetic acid hydrazide (15)having promising antifungal
activity with MIC of 4.1-16.5g/mL against an array of antifungal strains has been reported
by Wahab etal. Rasras et al. synthesized various cholic acid based hydrazones and screened
them as antifungal. The best compound among the series is reported to have MIC of 2g/mL
and 3.9g/mL against Escherichia faecalis and Escherichia coli. Anthraquinone based
hydrazones synthesized by Gouda et al. are reported to have promising antifungalostatic
activity against P. auriginosa.
Kumar et al. synthesized various benzyledine-hydrazides and reported their antifungal
activity against S. aureus. The agent is reported to have a MIC of 1.5M/mL.
Abdel-Wahab et al. synthesized differenthydrazone bearing imidazoles . The synthesized
compounds were screened for their antifungal activity against numerous strains. Vijesh et al.
synthesized 2,4- disubstituted thiazoles. The compound has a MIC value ranging between
1.6g/mL and3.1g/mL when tested against different strains.
Page 10

HO
N
N
N
N
H
OH
Cl
4-[(3-Chloro-pyrazin-2-yl)-hydrazonomethyl]-benzene-1,3-diol
Fig-14
Thomas et al .The activity of the newer agents is mostly tested against virulent H37Rv strain.
Few hydrazine derivatives synthesized by Raja et al. have been screened and reported to have
MIC of 6.3g/mL.4-hydroxy-8-trifluromethylquinolinederivatives with a MIC of0.625g/mL
have been reported by.
Vavrikova et al. synthesized fluorine-containing hydrazones with a MIC of 0.5g/mL and a
selectivity index of 1268.6 Pavan et al. synthesized some hydrazines with promising results.
Ferrocenyl hydrazones with a MIC of 0.75 and0.7mol/L have been reported by.
Mahajan et al. synthesized ferrocene-based hydrazone derivatives with significant potential.
Eswaran et al. synthesized hydrazones with a MIC of6.25g/mL. Jordao et al. synthesized
hydrazone derivatives with antifungal activity. The compound is reported to have MIC of
2.5g/mL. Fungal species are known to cause many superficial and systemic infections in
humans, plants as-well-as livestock. Hydrazone derivatives synthesized by Ozdemir et al.
after being screened against different Candida spp have been reported to have promising
antifungal potential.
Page 11

O
CH3
N
N
N
O
1-[5-(2-Phenoxymethyl-phenyl)-2-phenyl-[1,2,3,4]oxatriazol-3-yl]-ethanone
Fig-15
Newly prepared compounds were also screened for their antifungal activity against
Aspergilus flavus (NCIM No. 524), Aspergilus fumigatus (NCIM No. 902), Penicillium
marneffei (recultured) and Trichophyton mentagrophytes (recultured) in DMSO by serial
plate dilution method . Sabourands agar media was prepared by dissolving peptone (1 g), D
glucose(4g) and agar (2g) in distilled water (100 mL) and adjusting the pH to 5.7. Normal
saline wasused to make a suspension of sore of fungal strains for lawning. A loopful of
particular fungal strain was transferred to 3 mL saline to get a suspension of corresponding
species. Twenty milliliters of agar media was poured +into each Petri dish. Excess of
suspension was decanted and plated were dried by placing in an incubator at 37 C for 1h.
Using a punch wells were made on these seeded agar plates. Minimum inhibitory
concentrations of the test compounds in DMSO were added into each labeled well. A control
was also prepared for the plates in the same way using solvent DMSO. The Petri dishes were
prepared in triplicate and maintained at 37 C for 3-4 days. Antifungal activity was determined
by measuring the diameter of inhibition zone.Activity of each compound was compared with
cyclopiroxolamine as standard.
Page 12
ANTIPROTOZOL
H
N
H3CO
N
NH2
H3CO
H
H
C-[N'-(4,5-Dimethoxy-6,7-dimethyl-indan-1-ylidene)-hydrazino]-methylamine
Fig-16
Protozoal diseases are highly prevalent in tropical countries affecting human and animal
populations and causing suffering and death.Caputto et al. reported the inhibitory activity of
hydrazones against cruzipena major cysteine protease of T.cruzi. Hayat et al. reported the invitro antiamoebic activityof hydrazones against the HM1: IMSS strain of Endamoeba
hertolytica. The compounds are reported to have IC50 value of 0.03 and0.04M respectively.
Vaio et al. synthesized hydrazone derivatives and described them to be of high utility in
Chagas disease.
Siddiqui et al. described the anti amoebic activity of hydrazone derivatives . Romeiro et al.
developed hydrazine derivatives as cruzin inhibitors.Aponte et al. (2010) evaluated the anti
trypanosomal activity of hydrazone derivatives.
Page 13
ANTICANCER
NO2
N
H
N
N
2-Acetyl-5-methyl-4-[(2-nitro-phenyl)-hydrazono]-2,4-dihydro-pyrazol-3-one
Fig-17
Cancer is a lethal group of diseases with high level of penetrating potency affecting almost
every organ of the body. Al-Said et al. synthesized compound active against human breast
cancer cell lines MCF7.
Hassan et al. synthesized pyrazole based hydrazone derivatives with potential to treat breast
carcinoma.
Kendall et al. evaluated some derivatives as PI3K p110inhibitors. P13K are signalling
proteins indifferent cell types responsible forphosphorylation of lipids in cell membranes.
Kumar et al. Synthesized variousbis (indolyl) based hydrazones active against multiple
cancer cell lines.
Effenberger et al. reported a hydrazone derivative with potent activity against HL-60
leukaemiaand 518A2 melanoma. Acylhydrazones byCui et al. have been reported to have
potent activity against the human promyelocytic leukemic cells (Hl-60). Copper based
hydrazone derivatives are reported to act against integrin 4 in H322 lung carcinoma cell .
Palladium based hydrazones by Abu-Surrah et al. have been reported to be active against
human head and neck squamouscarcinoma cell lines SQ20B and SCC-25. 2-phenylindole
based hydrazone synthesized by El-Nakkady et al. have been developed against breast
carcinoma cell linesand reported to have an IC50 of 1.60nM.
Page 14

H3CO
H3CO
N
HN
C
H
H3CO
1,2,3-Trimethoxy-5-styryl-benzene
Fig-18
Linhong Jinet al have synthesizedsome 3acetyl2substituted phenyl5(3,4,5trimethoxyphenyl)
2,3dihydro1 ,3 ,4oxadiazole derivatives by cyclization reaction of N'substituted
benzylidene3,4,5trimethoxybenzohydrazide in acetic anhydride. The antitumor activities in

vitro of these compounds were evaluated against PC3, BGC823, and Bcap37 cells by MTT
method. They found that compound have strong inhibitory activity against PC3 cells. Among
these compounds, are much more active against PC3 cells than the other ones, with inhibition
rate of 70.6%. For the high active compounds further bioassay was conducted and their IC50
values against PC3 cells. Dalip Kumar et al have made a facile, convenient and high yielding
synthesis of a series of novel 5(3'indolyl)2(substituted)1,3,4 oxadiazoles from readily
available starting materials. The key step of ther protocol is oxidative cyclization of
Nacylhydrazones using [bis(trifluoroacetoxy)iodo] benzene under solvent free condition.
They studied the Structure Activity Relationship (SAR) of synthesized
indolyl1,3,4oxadiazoles by screening in vitro for their anticancer potential against human
cancer cell lines from prostate (PC3,DU145 and LnCaP), breast (MCF7 and MDMDA231),
and pancreas (PaCa2).Most of the compounds decreased cell viability significantly as
established by colorimetric MTT mitochondrial assay with IC50 values ranging from 1 lM to
1mM concentration. The SAR study reveals that substitution atthe C2 position of the
1,3,4oxadiazole ring plays an important role. The compound with C2 phenyl group
exhibited moderate activity against MCF7 (388.4 lM) and poor activity against other cell
lines. Also, Nmethylation of indole ring nitrogen dramatically improved the cytotoxic
activity. Studies are being conducted to determine mode of action of 5(30indolyl)
2(substituted)1,3,4oxadiazoles, and further modification of these compounds may
successfully lead to development of a potent anticancer agent.
Page 15

O
CH3
H3CO
N
N
H3CO
O
H3CO
1-[2-Phenyl-5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazol-3-yl]-ethanone
Fig-19
A new series of adamantanyl1,3thiazole and 1,3,4oxadiazole derivatives bearing various

aryl groups has been synthesized from adamantan1nitrile in four steps by Maryam
Zahidetal. They used Adamantan1nitrile as a starting material for the synthesis of target
compounds. The nitrile was converted into thioamide, using P4S10followed by its treatment
with ethyl bromo pyruvate to afford Ethyl 2adamantyl1,3thiazole4carboxylate 4.
Hydrazinolysis of gave the carbohydrazide1,3thiazole 5. Heating 5 with substituted benzoic
acids in the presence of polyphosphoric acid (PPA) furnished 1,3,4oxadiazole derivatives .
They evaluated all the compounds, in vitro, for anti proliferative activity against a large panel
of human tumorderived cell lines. Compounds 6eexhibited activity against human splenic
Blymphoblastoid (WIL2NS) and human acute Blymphoblastic leukemia (CCRFSB) cell
lines with CC 50= 68 and 42 M, respectively. Compound 6lshowed activity against
CCRFSB cell lines with CC50= 51 M. All the other compounds were found inactive.
Page 16
ANTIINFLAMMETERY
O
H
N
N
H
N
N
O
4-Methyl-furazan-3-carboxylic acid N'-(3-isopropyl-phenyl)-hydrazide

Fig-20
Much work has been done describing the analgesic and anti-inflammatory potential of
hydrazides.
Harnandez et al. reported analgesic and anti-inflammatory activity offuroxanyl-Nacylhydrazones.
Rajitha et al. evaluated the anti-inflammatory activity of some aryl hydrazones and gotgood
results.
Moldovan
et al. synthesized various hydrazone derivatives and reported them to have
promising in-vivo anti-inflammatory activity.

El-Sayed et al. synthesized hydrazone derivatives
with selectiveCOX-2 inhibition. The
compound is reported to have an ED50 value of 0.2 mmol/Kg.

N
N
OCH3
N
O
4-[5-(3-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine
Fig-21
The activity was carried out using Winter et 01. Carrageen an induced paw-edema me tho in
albino rats(6 rats in each group). Indomethac in 20 mg/kg wasused as the reference drug. All
Page 17

the test compounds (20mg/kg) were given orally as carboxymethyl cellulosesuspens ion I hr
before 0 .05 mL of carrageenan injection(1 % w/v suspension) into the sub plantar region of
the right hind paw of rats. The paw volume was determined plethys mographically before and
after 3 hr of injecting carrageenan and the percentage inhibits on of edema of the standard
and the test compounds was calculated us in g equation .Inhibition (%)=[{(VI.Vo) control(VI.Vo) treated } /(VI.Vo) control] X LOO (1) (VI and Vo related to the average volume in
the hind paw of the rats before any treatment and after anti-inflammatory agent treatment
respectively). The anti-inflammatory activity of the compounds synthesised was observed at
3 hr. The statistical analysis was done by student's t test.
C
N
N
Thiobenzoic acid S-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl) ester

Fig-22
Carageenan induced rat paw edema was a valuable test used in predicting the activity of antiinflammatory agents that act by inhibiting the mediators of acute inflammation. Randomly
selected molecule, about five in number from the set of synthesized compounds, were
evaluated for the activity at a dose of about 500mg/kg body weight. The results observed for
anti-inflammatory activity by Carrrageenan induced rat paw edema is given in table Test
compounds when administered orally produce significant anti-inflammatory activity in
carrageen induced rat paw edema model at 500mg/kg body weight comparable with that of
indomethacin10mg/kg body weight. The analysis of result shows that the compound shows
maximum activity .Study of the biological activity shows the title compound are having
significant NSAID action similar to that of indomethacin.Therest of the biological screening
is supported by the inference we got from study of molecular properties.
O
Br
N
1-(4-Bromo-phenyl)-3-[1,3,4]oxadiazol-2-yl-propan-1-one
Fig-23
Page 18

Asif Hussain et al reported a novel series of 2-[3-(4-bromophenyl)propan-3-one]- (substituted
phenyl)]1,3,4-oxadiazoles and have been synthesized from 3-(4- bromobenzoyl) propionic
acid with the aim to get better anti inflammatory agents with minimum or without side
effects. These were evaluated them for anti inflammatory activity according to the method of
Winter et al. on Wistarrats. The rats were divided into thirteen groups of six animals each.
Freshly prepared aqueous suspension of carrageen an (1 % m/V, 0.1 mL) was injected in the
planta aponeurosis of the right hind paw of each rat. One group was kept as a control and the
animals of othergroups were pre-treated with test drugs (20 mg kg.1 body mass) given orally
30 minutes before carrageen an injection. The foot volume was measured before and 4 h after
carrageen an injection with a plethysmograph. Themean increase in the paw volume in each
group was calculated. Indomethacin used as standard drugs forcomparison.1,3,4oxadiazole
and its derivatives
were synthesized by Dannay Dewangan et al using intermediate
pyridine4Carbohydrazide. Schiffs base were obtained on treatment with various aromatic

aldehyde,further on condensation with acetic anhydride produced the title compounds. They
also synthesized derivative of 1,3,4 oxadiazole (4,5,6) using same intermediate as above by
different methods. They also studied SAR of these synthesized compounds .The 2position
and 5position is an extremely important site of molecule are modification,which play a
dominant role in determining the pharmacological activites of 1,3,4 oxadiazole derivatives.
The synthesized compounds were screened using carrageen eaninduced rat paw edema.
Direct substitution of the 2 position with an C5H4N, with pyridine in 5position enhance the
antiinflammatory activity of 1, 3, 4oxadiazole derivative. Few compounds like compound
were shows good anti inflammatory activity against standard .
Page 19

ANTIMICROBIAL
O
N
N
H
2-[1,3,4]Oxadiazol-2-yl-1H-indole
Fig-24
A series of 1,3,4bisoxadiazole derivatives were developed by Ahmed O. Maslat1 et al as

potential antimicrobial agents. The compounds are:
5,5dimercaptobis[1,3,4oxadiazol2yl]propane
,5,5dimercaptobis[1,3,4oxadiazol2yl]butane,
5,5dimercaptobis[1,3,4oxadiazol2yl]octaneand
5,5dibenzylthiobis[1,3,4oxadiazol2yl]butane.
These newly synthesized compounds were investigated for their antibacterial, antifungal
activities against S. aureussand B. subtilis. Compound 2a also showed activity against
P.aeureoginosa. All the above compound exhibited activity against C. albicans. Niti
Bhardwaj2et al have synthesized derivatives of 1,3,4oxadiazoles by incorporating indole
nucleus at one of the two free positions in the oxadiazole ring system. These synthesized
compounds evaluated for antimicrobial activity by Punchedhole method against MTCC 441
(Bacillussubtilis), MTCC 1430 (Staphylococcus aureus), MTCC 424(Pseudomonas
aeruginosa), MTCC 1573 (Escherichia coli) and MTCC 2546 (A. niger) respectively using
the standard drugs nor ofloxacin and fluconazole. The activity was observed in compound
R1(against B.subtilis and P.aeruginosa), R2 (against S.aureus, E.coli and B. subtilis)
and(against S.aureus). None of the compounds were found effective against A. niger. Out of
these 4 compounds, only three were found effective against bacterial strains and none of the
synthesized compound was found effective against fungal strain. The compounds which were
active against bacterial strains were effective at a much higher concentration as compared to
the standard drug.
Page 20

OH
O
N
N
N
H
4-[5-(1H-Indol-2-yl)-[1,3,4]oxadiazol-2-yl]-phenol
Fig-25
Asif
Husainet
al
have
synthesized
novel
series
of
2[3(4bromophenyl)
propan3one]5(substituted phenyl)1,3,4oxadiazoles from 3(4bromobenzoyl) propionic

acid as starting material in the reaction with different aryl acid hydrazidesin phosphorous ox
chloride
and
screened
for
antibacterial
activity
by
using
Gram
positive
(Staphylococcusaureus) and Gram negative (Escherichia coli) bacterial strains. The test was
carried out in meat peptone agar medium at a concentration of 100 mg mL1 by the cup plate
method. Nitrofurazone was used as standard drug for comparison. Compound
2[3(4bromophenyl) propan3one]5(4fluorophenyl)1,3,4oxadiazole showed very good
activity against S. aureus (MIC = 12.5 mg mL1) and good activity against E. coli (MIC = 25
mg mL1), whereas 2[3(4bromophenyl)propan3one]5(4chlorophenyl)1,3,4oxadiazole
(4c) showed good activity against S. aureus (MIC = 25 mg mL1). The reference drug,
nitrofurazone showed MIC of 12.5 mg mL1 against S. aureus and 6.5 mg mL1 against E.
coli. None of the compounds showed activity equivalent to that of the standard drug
Nitrofurazone except compound 4f, which showed at par activity to that of the standard
against S. aureuswith MIC of 12.5 mg mL1.
Br
2-(6-Bromo-naphthalen-2-yloxymethyl)-furan
Fig-26
Page 21

A series of new 1,3,4oxadiazole derivatives having 6bromonaphthalene moiety are
synthesized by H. S.Yathirajan4et al using 2[(6bromo2naphthyl)oxy]acetohydrazide and
various substituted aromaticacids in the presence of POCl3. They also synthesized
5{[(6bromo2naphthyl)oxy]methyl}1,3,4oxadiazole2(3H)thioneusing
hydrazide,
CS2and KOH. These synthesized compounds were further subjected to Mannich reaction to
get a series of Mannich bases. All the newly synthesized compounds were screened for their
antimicrobial activity. The investigation of antibacterial and antifungal screening data
revealed that all the tested compounds showed moderate to good inhibition at g ml1 in
DMSO. The compounds showed comparatively good activity against all the bacterial strains.
The good activity is attributed to the presence of pharmacologically active group attached to
phenyl group at position 5of the oxadiazole ring. Introduction of aryl moiety carrying chloro
and dichloride group enhanced activity compared to the standard against T. mentagrophytes,
A. flavusand A. fumigatus. The presence of NMannich base has showngood antibacterial
and antifungal activity. Among the tested compounds, Mannich bases have shown
remarkable activity against all tested microorganisms. Ther may be attributed to the presence
of pharmacologically activemorpholine, 4methylpiperazine, 2fluorophenyl, 4chlorophenyl
and 2methylphenyl groups associated withoxadiazole ring, while Smethylation caused
decrease inactivity against most of the strains. The compounds were inactive compared to
that of standard against all the bacterialand fungal strains.
Neeraj Kumar Fuloria et al have made a series new:
1(2aryl5phenethyl1,3,4oxadiazol3(2H)yl) ethanones was synthesized by the
cyclization of imines 1aeusingaceticanhydride. These products were evaluated for
antibacterialand antifungal activity against freshly culturedstrains of S. aureus (SA) and P.
aeruginosa (PA) using sterile nutrient agar media and for antifungal activity against freshly
cultured strains of C. albicans (CA) and A. flavus (AF) using sterile sabourauds agar
medium by the disk diffusion method at a concentration of 2 mg per mL using DMF as
solvent. The results were recorded in duplicate using ampicillin and fluconazole at a
concentration of 1 mg per Ml as standards. Compounds were found to be equipotent to
ampicillin when tested against the strains of S.aureus, and P. aeruginosa, whereas some of the
newly synthesized compounds like were found to possess good antibacterial and antifungal
activity when tested against S. aureus, P. aeruginosa, C. albicans and Afflatus. Finally they
conclude that parsubstitution enhancesthe activity of synthesized oxadiazoles.
Page 22
ANTITUBERCULARACTIVITY:
S
O
N
N
N
H
H
N
S
O
N
2-[(4-{4-[1-(3-Thioxo-3H-pyrrol-2-yl)-ethylamino]-benzenesulfonyl}-phenylamino)-methyl]-2,4dihydro-pyrazole-3-thione
Fig-27
Mohamed Ashraf Ali et al have synthesized series of oxadiazole mannich bases derivatives,
dapsone and appropriate aldehyde in the presence of methanol. There action procedure is
based on the condensation and ring closure reaction of appropriate acid hydrazide with
carbon disulfide (CS2). All the synthesized oxadiazole underwent condensation with
appropriate aromatic aldehyde and dapsone in methanolic solution (reaction time varies
from8 to 22 h) affording titled mannich bases. The synthesized compound was tested for their
anti-mycobacterial activity in vitro against MTB and INHRMTB by agar dilution method
using double dilution technique. They reported that eleven compounds exhibited excellent
anti-mycobacterial activity with MIC ranging from 0.1 to 5.96 lM. Among the synthesized
compounds,
3{2furyl[4(4{2furyl[5(2naphthyloxymethyl)2thioxo2,3dihydro1,3,4oxadiazolyl]me
thylamino}phenylsulfonyl)anilino]methyl}5(2naphthyloxymethyl)2,3dihydro1,3,4oxadi
azole2 thione was found to be most potent compound and was 7.3foldagainst MTB and
10.3fold against INH resistant MTB more active than isoniazid. These anti-mycobacterial
data clearly show that the presence of furfural with 2naphthoxymethylsubstitution at
mannich bases causes remarkable improvement in Ant tubercular activity against both M.
tuberculosis H37Rvand INH resistant M. tuberculosis.
Page 23
CONHNH2
4-Pyrrol-1-yl-benzoic acid hydrazide
Fig-28
S.D. Joshi et al reported a novel series of 4-pyrrol-1-yl benzoic acid hydrazide (a) analogs,
some derived 5-substituted-2-thiol1,3,4oxadiazoles (b), 5-substituted-4-amino-1,2,4triazolin-3- thione and 2,5dimethyl pyrroles (c)and these have been synthesized in good
yields and characterized by IR, NMR, mass spectral and elemental analyses. These
compounds were screened for antitubercular activity against Mycobacterium tuberculosis
H37Rv strain by broth dilution assay method. compounds containing the 1,3,4]oxadiazoline
ring and acetyl group, show better activity against M. tuberculosis H37Rv and compound 3
showed highest activity (MIC 16 mg/mL). They selected these compounds for further
development to acquire more information about structure]activity relationships in their
laboratories.
Krishna Kant Jha12 et a reported 3D QSAR studies for the41 molecules of 1,3,4oxadiazoles
by using kNearest Neighbour Molecular Field Analysis (kenMFA) combinedwith various
selection procedures using kNNMFAapproach 52 3DQSAR models were generated. Ther
model can be used for preliminary screening of large diversified compound libraries. The
model has shown that presence of sulphur is must for activity, however the larger bulky
substituents reduce the activity. The presence of halogen and other nonhalogen groups have
also contributed to the activity. Hence the future schemes with smaller groups on sulphur and
electronegative groups in the molecule would result in potentially active molecules.
Page 24

ACTIVE MOITY RESPONSIBLE FOR PHARMACOLOGICAL ACTIVITY
N
H
N
2,6-Dichloro-N-(3-chloro-5-trifluoromethyl-pyridin-2-ylmethyl)-benzamide
Fig-29
H
N
N
N-(Benzylidene-hydrazinocarbonylmethyl)-N-(2,3-dichloro-phenyl)-benzamide
Fig-30
NH
NH
Indan-1,3-diylidenediamine
Fig-31
Page 25

HO
N
N
N
N
H
4-[(3-Chloro-pyrazin-2-yl)-hydrazonomethyl]-benzene-1,3-diol
Fig-32
O
H
N
N
H
N
N
O
4-Methyl-furazan-3-carboxylic acid N'-(3-isopropyl-phenyl)-hydrazide

Fig-33
NO2
N
H
N
N
2-Acetyl-5-methyl-4-[(2-nitro-phenyl)-hydrazono]-2,4-dihydro-pyrazol-3-one
Fig-34
Page 26

H
N
N
NH2
H
H
C-[N'-(4,5-Dimethoxy-6,7-dimethyl-indan-1-ylidene)-hydrazino]-methylamine
Fig-35
N
N
H
2-Phenoxymethyl-benzoic acid benzylidene-hydrazide

Fig-36
N
O
4-[5-(3-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine
Fig-37
Page 27
C
N
N
Thiobenzoic acid S-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl) ester

Fig-38
Page 28
CONCLUSION
Oxadiazole has been reported to have many biological activities like analgesic, antiinflammation, antimicrobial, anticancer, antidiabetic and others. Therefore ,Oxadiazole are
the molecules having diverse activity but still there are lot many things to be explored about
these versatile compounds. An attempt was done to summarize the reactions and biological
activity of Oxadiazole in ther review.
Page 29
REFERENCE
1. B. Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah, R. Narender, Synlett, 2010, 391394.
2. J. Roh, T. V. Artamonova, K. Vvrov, G. I. Koldobskii, A.
Hrablek, Synthesis, 2009, 2175-2178.
3. D. Cantillo, B. Gutmann, C. O. Kappe, J. Am. Chem. Soc., 2011, 133, 4465-4475
4. D. Cantillo, B. Gutmann, C. O. Kappe, J. Am. Chem. Soc., 2011, 133, 4465-4475.
5. M. M. Heravi, A. Fazeli, H. A. Oskooie, Y. S. Beheshtiha, H.
Valizadeh, Synlett, 2012, 23, 2927-2930.
6. W.-K. Su, Z. Hong, W.-G. Shan, X.-X. Zhang, Eur. J. Org. Chem., 2006, 2723-2726.
7. J.-J. Shie, J.-M. Fang, J. Org. Chem., 2007, 72, 3141-3144.
8. L. El Kaim, L. Grimaud, P. Patil, Org. Lett., 2011, 13, 1261-1263.
9. A. R. Katritzky, C. Cai, N. K. Meher, Synthesis, 2007, 1204-1208.
10. Y.-H. Joo, J. M. Shreeve, Org. Lett., 2008, 10, 4665-4667.
11. S. Hajra, D. Sinha, M. Bhowmick, J. Org. Chem., 2007, 72, 1852-1855.
12. J. K. Laha, G. D. Cuny, Synthesis, 2008, 4002-4006.
13. J. M. Keith, J. Org. Chem., 2006, 71, 9540-9543.
14. Z.P. Demko and K.B. Sharpless, J. Org. Chem., 66 (2001) 7945
15. Z.P. Demko and K.B. Sharpless, Org. Lett., 4 (2002) 2525-2527
16. O. G. ManchenO and C. Bolm, Org. Lett., 9 (2007) 2551
17. J. Bonnamour and C. Bolm, Chem. Eur. J. 15 (2009) 4543 4545
18. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo and L. Vaccaro, J. Org. Chem., 69
(2004) 2896.
19. G. Venkateshwarlu, A. Premalatha, K. C. Rajanna, and P. K. Saiprakash Synthetic
Communications 39 (2009) 44794485.
20. G. Venkateshwarlu a , K. C. Rajanna a & P. K. Saiprakash a Synthetic
Communications, 39 (2009) 426432.
21. M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Letters 50 (2009)
44354438.
Page 30

22. L. Lang, B. Li, W. Liu, Li Jiang, Z. Xu and G. Yin, Chem. Commun., 46 (2010) 448
450.
23. J. He, B. Li, F. Chen, Z. Xu, and G. Yin, J. Mol. Catal. A, 304 (2009) 135-138
24. B. Schmidt, D. Meid and D. Kieser, Tetrahedron, 63 (2007) 492.
25. T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 49 (2008) 2824.
26. M. Lakshmi Kantam, K.B. Shiva Kumar and K. Phani Raja, J. Mol. Catal. A, 247
(2006) 186.
27. M. Laxmi Kantam, V. Balasubramanyam and K.B. Shiva Kumar, Syn. Commn., 36
(2006) 1809-1814.
28. Dhayanithi Varadaraji P.G. and Research Department of Chemistry, Islamiah College,
Vaniyambadi 632 752, India.
29. Syed S. Suban Chemistry Division, School of Science and Humanities, VIT
University, Vellore 632 014, India
30. Venkat R. Ramasamy Department of Biochemistry, K.S. Hegde Medical Academy,
Mangalore 574 162, India
31. Kumaran Kubendiran P.G. and Research Department of Chemistry, Islamiah College,
Vaniyambadi 632 752, India
32. Jai Sankar K. G. Raguraman P.G. and Research Department of Chemistry, Islamiah
College, Vaniyambadi 632 752, India
33. Suchetha K. Nalilu Department of Biochemistry, K.S. Hegde Medical Academy,
Mangalore 574 162, India
34. Hari. N. Pati Department of Chemistry, Sambalpur University, Jyoti Vihar 768 019,
India
35. Ram Shankar Upadhayaya , Sanjay Jain ,Neelima Sinha , Nawal Kishore ,Ramesh
Chandra , Sudershan K. Arora , Synthesis of novel substituted tetrazoles having
antifungal activity,European Journal of Medicinal Chemistry ,2004,39, 579592
36. A. Rajasekaran , P.P. Thampi, Synthesis and analgesic evaluation of some5-[-(10phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles, European Journal of Medicinal
Chemistry ,2004,39, 273279
37. Umarani Natarajan, Ilango Kaliappan, Narendra Kumar Singh, A facile design and
efficient synthesis of schiff's bases of tetrazolo[1,5-a] quinoxalines as potential antiinflammatory and anti-microbial agents, Der Pharma Chemica, 2010, 2(1): 159-167
Page 31

38. Aiyalu Rajasekaran,Kalasalingam Ananda Rajagopal, Synthesis of some novel
triazole derivatives as anti-nociceptive and antiinflammatory agents, Acta
Pharm.2009,59,355364.
39. Wagle S.,Adhikari A.V.,Kumari S.K., synthesis of some new 4-styryltetrazolo [1,5-a]
quinoxaline derivatives as potent anticonvulsants, European Journal of Medicinal
Chemistry ,2009,44,1135-1143.
40. V. H. Bhaskar, P. B. Mohite, synthesis,characterization and evaluation of anticancer
activity of some tetrazole derivatives , Journal of Optoelectronics and Biomedical
Materials , October-December 2010, Vol.2 Issue 4, 249 259.
41. M.A.KALE AND M.R.PEHARKAR Department of Pharmaceutical Chemistry,
Government College of Pharmacy, Aurangabad-431005, Maharashtra State, India.
42. Pattan S.R.,Kekare P.,Patil A.,Nikalge A.,Kittur B.S., studies on synthesis novel
2,4thiazolidinedione derivatives containing tetrazole ring for their Antidiabetic
activity,Iranin journal of pharmaceutical sciences,2009,5(4),225-230.
43. Javid Shahbazi Mojarrad Department of Medicinal Chemistry, Faculty of Pharmacy,
Tabriz University of Medical Sciences, Tabriz, Iran
44. SUBRAMANIYAN ARULMURUGAN HELEN P. KAVITHA Research Department
of Chemistry SRM University, Ramapuram, Chennai Tamil Nadu, India
45. E. HOLBOV, E. SIDOV Institute of Chemistry, Komensk University, CS-842
15 Bratislava
46. Amir M, Khan MSY, Zaman MS. Ind J Chem 2004; 43B: 2189.
47. Hrib N, Jurcak J, Flavgare. J Med Chem 1992; 35: 2712.
48. Desyk RB, Zimenkovsky RS. Current Org Chem 2004; B: 1547.
49. Biradar JS, Manjunath SY. Ind J Chem 2004; 43 (B): 389.
50. Srivastava V, Singh S, Gulati A, Shankar S. Ind J Chem 1987; 26B: 652.
51. Loscher WG. Eur J Pharmacol 1948; 342.
52. Ei-Said, M. K. Pharmazie 1981, 36, 86-89.
53. Tilak, S. R. Et al. Indian drugs.1998, 35, 221.
54. Dominguez, J. N.; Lpez, S.; Charris, J.; Iarruso, L.; Lobo, G.; Semenov, A.; Olson, J.
E.; Rosenthal, P. J. J. Med. Chem. 1997, 40, 2726.
55. Lin, G.; Midha, K. K.; Hawes, E. M. J. Heterocycl. Chem. 1991, 28, 215.
56. Raval, J.; Desai, K. K. ARKIVOC, 2005, (xiii), 21.
57. Viveros, M.; Amaral, L. Int. J. Antimicrob. Ag. 2001, 17, 225.
Page 32

58. Amaral, L.; Kristiansen, J. E. Int. J. Antimicrob. Ag. 2000, 14, 173.
59. V. H. Bhaskar, P. B.Mohite, R. B. Pandhare, S. G. Khanage, Acta pharm.sci 52,504
(2010).
60. Mulwad V.V.;Pawar rupeshb. ; Chaskar Atul C, J. Korean Chem.Soc. 52,(3), 249
(2008).
Page 33

A Review On Oxadiazole. 2015 05 03 09 52 06 674

Hochgeladen von

Dokumentinformationen

Originaltitel

Copyright

Verfügbare Formate

Dieses Dokument teilen

Dokument teilen oder einbetten

Freigabeoptionen

Stufen Sie dieses Dokument als nützlich ein?

Sind diese Inhalte unangemessen?

Copyright:

Verfügbare Formate

A Review On Oxadiazole. 2015 05 03 09 52 06 674

Hochgeladen von

Copyright:

Verfügbare Formate

A Review on Oxadiazole derivatives

ANTIDIBATIC PROPERTY OF OXADIAZOLE

A series of new derivatives of 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazol-2(3H)-thione

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

the drug standard. The compounds 4-[5-(2-chlorophenyl)-1,3,4-

oxadiazol-2-yl]benzenamine and 3-{[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-2-{2[2,6-dichlorophenyl)amino]benzyl}-6-iodoquinazolin-4(3H)-one were respectively 2 and 5

A Review on Oxadiazole derivatives

A series of 2,5-diphenyl-1,3,4-oxadiazole derivatives for detecting diabities. The affinity for

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

In seeking broad spectrum pharmacological activities of benzimidazole derivatives, a group

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

2-Phenoxymethyl-benzoic acid benzylidene-hydrazide

pneumoniae (recultured) bacterial stains by serialplate dilution method .

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

benzylidene3,4,5trimethoxybenzohydrazide in acetic anhydride. The antitumor activities in

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

A new series of adamantanyl1,3thiazole and 1,3,4oxadiazole derivatives bearing various

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

4-Methyl-furazan-3-carboxylic acid N'-(3-isopropyl-phenyl)-hydrazide

et al. synthesized various hydrazone derivatives and reported them to have

promising in-vivo anti-inflammatory activity.

with selectiveCOX-2 inhibition. The

compound is reported to have an ED50 value of 0.2 mmol/Kg.

A Review on Oxadiazole derivatives

Thiobenzoic acid S-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl) ester

A Review on Oxadiazole derivatives

were synthesized by Dannay Dewangan et al using intermediate

pyridine4Carbohydrazide. Schiffs base were obtained on treatment with various aromatic

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

A series of 1,3,4bisoxadiazole derivatives were developed by Ahmed O. Maslat1 et al as

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

propan3one]5(substituted phenyl)1,3,4oxadiazoles from 3(4bromobenzoyl) propionic

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

S.D.C.O.PHARMACY &VOCATIONAL STUDIES ,MUZAFFARNAGAR

A Review on Oxadiazole derivatives

4-Pyrrol-1-yl-benzoic acid hydrazide