DOI 10.

1007/s11094-017-1654-8
Pharmaceutical Chemistry Journal, Vol. 51, No. 7, October, 2017 (Russian Original Vol. 51, No. 7, July, 2017)

SYNTHESIS AND ANTI-INFLAMMATORY

ACTIVITY OF 2-{[5-(2-CHLOROPHENYL)-
4H-1,2,4-TRIAZOL- 3-YL]SULFANYL}-
1-(SUBSTITUTED PHENYL)ETHANONES

N. A. Karande1,* and L. G. Rathi1

Original article submitted May 12, 2016.

With the aim of obtaining potential anti-inflammatory compounds, 2-{[5-(2-chlorophenyl)-4H-1,2,4-triazol-

3-yl]sulfanyl}-1-(phenyl)ethanone and a series of its derivatives were synthesized, purified by flash chroma-
tography, and characterised by spectral and elemental analysis. All the new synthesized compounds were
evaluated for their anti-inflammatory activity using carrageenan-induced paw edema test on Wistar albino
rats. The results suggest that 1-(4-fluorophenyl)-2-{[5-(2-chlorophenyl)-4H-1,2,4-triazol-3-yl]sulfanyl}etha-
none 7l exhibit remarkable activity when compared with indomethacin even in the absence of carboxyl group
in its structure, which reduces the possibility of gastric irritation.
Keywords: 5-(2-chlorophenyl)-4H-[1,2,4]triazole-3-thiol; 2-bromo-1-(substituted phenyl)ethanone; anti-in-
flammatory activity.

INTRODUCTION tioxidant [14], and anticancer [15]. In the light of these, we

Non-steroidal anti-inflammatory drugs (NSAIDs) are
used in the treatment of pain, inflammation, fever, and a
number of arthritic diseases such as rheumatoid arthritis and
osteoarthritis [1, 2]. However, their therapeutic use is often
limited by common side effects, such as gastrointestinal (GI)
hemorrhage, perforation, and ulceration [3, 4]. The incidence
of clinically significant GI side effects due to NSAIDs is
high (30%) and causes some patients to abandon NSAID
therapy [5]. GI damage from NSAID is generally attributed
to two factors: (i) local irritation by the carboxylic acid moi-
ety that is common to most NSAIDs (topical effect) and (ii)
decreased tissue prostaglandin production, which under-
mines the physiological role of cytoprotective prostaglandins
in maintaining GI health and homeostasis [6, 7].
Hence in spite of abundance of NSAIDs in the market,
an ideal agent is still a dream and the search continues to de-
velop new drugs that have potent anti-inflammatory activity
with minimum side effects. Recent studies revealed that
compounds containing a 1,2,4-triazole skeleton exhibited
wide range of biological activities including anti-inflamma-
tory [8, 9], antimicrobial [10, 11], antitubercular [12, 13], an-
1
Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Ed-
ucation and Research, Borgaon (Meghe), Wardha 442001, India.
*
e-mail: n.k.0704@gmail.com
have attempted to synthesize new anti-inflammatory drugs
not possessing carboxylic groups.
EXPERIMENTAL PART
General
All the reagents and chemicals were procured from com-
mercial sources (SD Fine Chemicals, India; Aldrich, United
States; Merck, Germany) and used without any purification.
Solvents were freshly distilled and used. Melting points were
determined on a digital melting point apparatus DBK
10 MPA 03. All the reactions were monitored by thin-layer
chromatography (TLC) performed on 20 ´ 20 cm aluminium
sheets precoated with silica gel 60 F254. The infrared spectra
were recorded on a Shimadzu 8400S FT-IR spectrometer us-
ing KBr optics. The 1H NMR and 13CNMR spectra were re-
corded in DMSO-d6 on a Bruker Avance II 400-MHz spec-
trometer at frequencies of 400 MHz and 100 MHz, respec-
tively. Mass spectra were recorded on Waters Q-TOF
Micromass LC-MS mass spectrometer. Elemental analyses
were carried out using Perkin Elmer Series II CHNS/O ana-
lyzer and found within ± 0.4% of theoretical values. Flash
chromatography was carried out using CombiFlash Rf 200i
system.

558
0091-150X/17/5107-0558 © 2017 Springer Science+Business Media New York
Synthesis and Anti-Inflammatory Activity 559

Syntheses 5-(2-Chlorophenyl)-4H-1,2,4-triazole-3-thiol (5). To a

2-Chlorobenzoic acid (2). 2-Chlorobenzoic acid was
prepared by following reported method [16].
2-Chlorobenzohydrazide (3). To a solution of com-
pound 2 (0.01 mol) in methanol (20 mL), catalytic amount of
sulfuric acid (0.5 mL) was added and the reaction mixture
was refluxed for 2 h. The resulting ester was refluxed with
hydrazine hydrate (0.02 mol) in dry methanol for 6 h and, af-
ter cooling, a solid obtained was collected by filtration. The
product was washed with cold methanol, dried, and
recrystallized from methanol: yield, 93%; m.p., 113 – 115°C;
IR (KBr; n, cm–1): 3286.48 and 3184.26 (NH2), 3066.41
(Ar-H), 1645.17 (C=O).
{(2-Chlorobenzoyl)amino}thiourea (4). To a solution
of compound 3 (0.01 mol) in water (25 mL), potassium
thiocyanate (0.02 mol) and conc. HCl (2 mL) were added.
The reaction mixture was refluxed for 2 h and, after comple-
tion of the reaction, the mass was quenched into ice-cold wa-
ter (200 mL). The precipitated product was filtered, dried,
and recrystallized from ethanol: yield, 85%; m.p.,
132 – 134°C; IR (KBr; n, cm–1): 3415.70 (Sec. NH), 3294.19
and 3199.69 (NH2), 1677.95 (C=O), 1600.81 (Ar C=C).
5% solution of sodium hydroxide (100 mL), compound 4
(0.01 mol) was added and the mixture was refluxed for 3 h.
The reaction mixture was poured onto crushed ice with stir-
ring and neutralized with conc. HCl. The resulting solid was
filtered, washed with cold water, dried, and recrystallized
from ethanol: yield, 87%; m.p., 145 – 147°C; IR (KBr; n,
cm–1): 3415.70 (Sec. NH), 3056.96 (Ar-H), 2663.51 (S-H),
1604.66 (Ar C=C).
General procedure for synthesis of 2-bromo-1-(sub-
stituted phenyl)ethanones (6a – 6l). Compounds 6 were
prepared by following reported method [17].
General procedure for synthesis of 2-{[5-(2-chloro-
phenyl)-4H-1,2,4-triazol-3-yl]sulfanyl}-1-(substituted phe-
nyl)ethanones (7a – 7l). To a solution of compound 5
(0.01 mol) in ethanol (50 mL), 2-bromo-1-(substituted
phenyl)ethanone 6 (0.01 mol) and potassium hydroxide
(0.015 mol) were added and refluxed for 5 h. The reaction
mixture was cooled and poured onto crushed ice. The result-
ing solid was filtered, washed, with water, and dried. The
crude product was purified by flash chromatography using
hexane – ethyl acetate (1 : 1) mixture. The purified product
was recrystallized from ethanol. The yields and melting
points of compounds (7a – 7l) are listed in Table 1. The spec-

TABLE 1. Physicochemical and Analytical Characterization of Synthesized Compounds 7a – 7l

Molecular M.p., Calculated (Found), %

Compound Empirical Formula Yield, %
Weight °C C H N S
7a C16H12ClN3OS 329.80 152 – 154 90 58.27 3.67 12.74 9.72
(58.33) (3.72) (12.89) (9.23)
7b C16H11Cl2N3OS 364.25 167 – 169 92 52.76 3.04 11.54 8.80
(52.69) (3.08) (11.78) (8.31)
7c C16H11Cl2N3OS 364.25 175 – 177 82 52.76 3.04 11.54 8.80
(52.68) (3.07) (11.82) (8.42)
7d C16H11BrClN3OS 408.70 184 – 186 85 47.02 2.71 10.28 7.85
(47.09) (2.79) (10.02) (8.02)
7e C16H13ClN4OS 344.82 165 – 167 87 55.73 3.80 16.25 9.30
(55.78) (3.67) (16.09) (9.56)
7f C16H11ClN4O3S 374.80 138 – 140 94 51.27 2.96 14.95 8.56
(51.31) (3.01) (14.21) (8.98)
7g C16H11ClN4O3S 374.80 145 – 147 85 51.27 2.96 14.95 8.56
(51.32) (3.03) (14.38) (8.95)
7h C17H14ClN3OS 343.83 180 – 182 89 59.38 4.10 12.22 9.33
(59.44) (4.16) (12.35) (8.91)
7i C17H14ClN3O2S 359.83 178 – 180 89 56.74 3.92 11.68 8.91
(56.71) (3.98) (11.92) (8.43)
7j C16H12ClN3O2S 345.80 177 – 179 82 55.57 3.50 12.15 9.27
(55.62) (3.57) (12.47) (9.88)
7k C16H12ClN3O2S 345.80 188 – 190 95 55.57 3.50 12.15 9.27
(55.63) (3.59) (12.44) (9.82)
7l C16H11FN3OS 347.79 192 – 194 91 55.25 3.19 12.08 9.22
(55.30) (3.24) (12.32) (9.69)
560 N. A. Karande and L. G. Rathi

O O tral characteristics of synthesized compounds are given in

CH 3 KMnO4 OH Table 2.
Cl 70–80°C, 2h
Cl Anti-Inflammatory Activity Evaluation
1
2
In vivo anti-inflammatory activity was evaluated by us-
Conc. H2SO4 ing a method described by Winter, et al. [18]. Experimental
NH2NH2·H2O procedures were approved by the Institutional animal ethics
O committee. For the study, male albino rats weighing
H O
N NH2 165 – 220 g were used for the experiment. They were housed
N
H KSCN NHNH2 in clean wire netted polypropylene cages at controlled room
S
Cl Conc. HCl temperature (25°C), relative humidity (60 – 70%), and 12 h
4 Cl
3 light-dark cycle. The animals were maintained with standard
NaOH laboratory diet and water ad libitum. The animals were de-
prived of food 12 h before and during experimental hours.
O
The animals were divided randomly into 26 groups, each
N N containing 6 animals. A mark was created on the left hind
SH Br
N + R paw simply on the far side the tibio-tarsal junction, in order
H
6 that any time the paw was swaybacked within the mercury
Cl
5 column up to mounted mark constant paw volume was en-
sured. The initial paw volume of every rat was determined
KOH EtOH
plethysmometrically. The first group (control) received nor-
N N mal saline, and the second group received standard drug
S R
N
indomethacin at a dose of 1.5 mg/kg (p.o.). The 3rd to 14th
H O groups were administered test compounds 7a – 7l at a dose
Cl 7a-l of 50 mg/kg (p.o.) (at ALD50 > 800 mg/kg, p.o.). After
30 min of pretreatment with test compounds, 0.1 mL of 1 %
Where 7a R=H 7g R=4-NO 2 (w/v) carrageenan was injected within the subplantar region
7b R=2-Cl 7h R=4-CH 3
of the left hind paw. The right paw served as a reference to
7c R=4-Cl 7i R=4-OCH 3
7j R=2-OH noninflammed paw for comparison. The initial paw volume
7d R=4-Br
7k R=4-OH was measured within 30 sec of the injection. The relative in-
7e R=4-NH 2
7l R=4-F crease in paw volume was measured in control, standard, and
7f R=2-NO2
test compounds at 1, 2, 3, and 4 h after the carrageenan injec-
Scheme 1. Synthesis of 2-{[5-(2-chlorophenyl)-4H-1,2,4-triazol-3- tion. The difference between the two readings was taken as
yl]sulfanyl}-1-(substituted phenyl)ethanones. the volume of edema and the percentage inhibition of edema
by the test drugs was calculated using the following formula:

Fig. 1. Flash chromatogram of compound 7l.

Synthesis and Anti-Inflammatory Activity 561

% Edema inhibition = 100 – (Vtest/Vcontrol) ´ 100.
The results were expressed as percentage inhibition of
paw edema relative to the untreated control group. The re-
sults of anti-inflammatory testing are given in Table 3.
RESULTS AND DISCUSSION
Chemistry
A novel series of 2-{[5-(2-chlorophenyl)-4H-1,2,4-tri-
azol-3-yl]sulfanyl}-1-(substituted phenyl)ethanone 7a – 7l
were synthesized as shown in Scheme 1 by the reaction be-
tween 5-(2-chlorophenyl)-4H-1,2,4-triazole-3-thiol 5 and
2-bromo-1-(substituted phenyl)ethanones 6a – 6l. The start-
ing material 1-(2-chlorophenyl)ethanone 1 was converted
into 2-chlorobenzoic acid 2 by oxidation with potassium per-
manganate by following literature method. 2-Chlorobenz-
ohydrazide 3 was obtained by refluxing 2-chlorobenzoic acid
2 with hydrazine hydrate in methanol. Compound 3 on reac-
tion with potassium thiocyanate yielded corresponding
{(2-chlorobenzoyl)amino}thiourea 4 in good yield. The
5-(2-chlorophenyl)-4H-1,2,4-triazole-3-thiol 5 was synthe-
sized by cyclization in the presence of base. 2-Bromo-1-
(substituted phenyl)ethanones 6 were prepared by following
literature method.
Finally, 5-(2-chlorophenyl)-4H-1,2,4-triazole-3-thiol 5
was treated with 2-bromo-1-(substituted phenyl)ethanone
(6a – 6l) in the presence of base in ethanol medium to obtain
the corresponding 2-{[5-(2-chlorophenyl)-4H-1,2,4-triazol-
3-yl]sulfanyl}-1-(substituted phenyl)ethanone (7a – 7l).

TABLE 2. Spectral Characteristics of Synthesized Compounds 7a – 7l

Compound IR (KBr), n, cm–1 1
H-NMR (DMSO), d, ppm
7a 3286.48 (NH), 3037.68 (Ar-H), 2943.17 (CH2), 10.67 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 8.42 Hz), 7.81 (d, 2H, Ar-H,
1745.46 (C=O), 1616.24 (C=N) J = 8.12 Hz), 7.58 (s, 1H, Ar-H), 7.52 -7.41 (m, 2H, Ar-H), 7.29 (d, 2H, Ar-H,
J = 8.12 Hz), 7.17 (d, 1H, Ar-H, J = 7.48 HZ), 4.62 (s, 2H, CH2)
7b 3400-3200 (NH), 3068.53 (Ar-H), 2896.88 10.67 (s, 1H, NH), 7.94 (d, 1H, Ar-H, J = 7.42), 7.71 (t, 2H, Ar-H, J = 7.16 Hz),
(CH2) 7.52 (t, 2H, Ar-H, J = 8.68 Hz), 7.38 (q, 2H, Ar-H, J = 8.01 Hz), 7.17 (t, 1H,
Ar-H, J = 9.16), 4.57 (s, 2H, CH2)
7c 3400-3200 (NH), 3067.53 (Ar-H), 2896.88 10.68 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 8.78 Hz), 7.71 (t, 2H, Ar-H,
(CH2) J = 7.26 Hz), 7.52 (t, 2H, Ar-H, J = 7.26 Hz), 7.31 (q, 2H, Ar-H, J = 7.32 Hz),
7.17 (t, 1H, Ar-H, J = 9.32 Hz), 4.57 (s, 2H, CH2)
7d 3400-3200 (NH), 3068 (Ar-H), 2890 and 2845 10.67 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 7.49 Hz), 7.71 (t, 2H, Ar-H,
(CH2) J = 7.10 Hz), 7.58 (q, 2H, Ar-H, J = 8.84 Hz), 7.38 (t, 2H, Ar-H, J = 7.10 Hz),
7.17 (d, 1H, Ar-H, J = 7.81 Hz), 4.62 (s, 2H, CH2)
7e 3454.27 and 3332.76 (NH), 3124.47 (sp2 C-H), 10.68 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 7.25 Hz), 7.71 (t, 1H, Ar-H,
3055.03 (Ar-H), 2981.74 and 2896.88 (CH2) J = 7.82 Hz), 7.51 (t, 2H, Ar-H, J = 8.67 Hz), 7.41 (t, 2H, Ar-H, J = 9.44 Hz), 7.17
(t, 2H, Ar-H, J = 8.67 Hz), 4.66 (s, 2H, CH2), 4.06 (s, 2H, NH2)
7f 3298.05 (NH), 3097 (Ar-H), 2941.24 (CH2), 10.57 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 9.2 Hz), 7.78 -7.68 (m, 2H, Ar-H),
1616.24 (C=N), 1539.09 and 1319.22 (N-O) 7.58-7.48 (m, 2H, Ar-H), 7.38 (q, 2H, Ar-H, J = 8.12 Hz), 7.17 (d, 1H, Ar-H,
J = 7.98 Hz), 4.62 (s, 2H, CH2)
7g 3298.05 (NH), 3097.47 (Ar-H), 2941.24 (CH2), 10.57 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 8.17 Hz), 7.81-7.68 (m, 2H, Ar-H),
1616.24 (C=N), 1539.09 and 1319.22 (N-O) 7.58-7.41 (m, 2H, Ar-H), 7.38-7.29 (m, 2H, Ar-H), 7.17 (d, 1H, Ar-H,
J = 7.98 Hz), 4.62 (s, 2H, CH2)
7h 3290.33 (NH), 3031.89 (Ar-H), 2941.24 and 10.67 (s, 1H, NH), 7.94 (d, 1H, Ar-H, J = 9.12 Hz), 7.81 (d, 2H, Ar-H, J = 7.94),
2839.02 (CH2), 1731.96 (C=O), 1616.24 (C=N) 7.58-7.47 (m, 2H, Ar-H), 7.38 (d, 2H, Ar-H, J = 7.94 Hz), 7.17 (t, 1H, Ar-H,
J = 7.58 Hz), 4.57(s, 2H, CH2), 2.31(s, 3H, CH3)
7i 3265.26 (NH), 3074.32 (Ar C-H), 2964.39 and 10.67 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 7.52 Hz), 7.83-7.68 (m, 2H, Ar-H), 7.58
2850.59 (CH2), 1681.81 (C=O), 1614.31 (C=N), (t, 1H, Ar-H, J = 8.09 Hz), 7.51 – 7.38 (m, 2H, Ar-H), 7.34 – 7.21 (m, 2H, Ar-H),
1591.16 (Ar C=C) 4.62 (s, 2H, CH2), 3.72 (s, 3H, OCH3)
7j 3384.84 (O-H), 3035.75 (Ar-H), 2985 and 10.67 (s, 1H, NH), 9.72 (s, 1H, OH), 7.94 (d, 1H, Ar-H, J = 7.03 Hz), 7.74 (t, 2H,
2833.24 (CH2), 1695.31(C=O) Ar-H, J = 7.16 Hz), 7.62 (s, 1H, Ar-H), 7.51 (q, 2H, Ar-H, J = 7.08 Hz), 7.31 (t,
2H, Ar-H, J = 8.07 Hz), 4.62 (s, 2H, CH2)
7k 3384.84 (O-H), 3035.75 (Ar-H), 2985.60 and 10.77 (s, 1H, NH), 9.72 (s, 1H, OH), 7.94 (d, 1H, Ar-H, J = 7.13 Hz), 7.78 – 7.71
2833.24 (CH2), 1695.31(C=O) (m, 2H, Ar-H), 7.68 – 7.58 (m, 2H, Ar-H), 7.52 – 7.24 (m, 3H, Ar-H), 4.62 (s, 2H,
CH2)
7l 3400 – 3200 (NH), 3068.53 (Ar-H), 2931.60 and 10.67 (s, 1H, NH), 7.91 (d, 1H, Ar-H, J = 7.82 Hz), 7.73 (q, 2H, Ar-H,
2896.88 (CH2) J = 7.32 Hz), 7.62 (d, 1H, Ar-H, J = 7.91 Hz), 7.41 (t, 2H, Ar-H, J = 8.04 Hz),
7.31 (q, 2H, Ar-H, J = 7.32 Hz), 4.62 (s, 2H of CH2)
562 N. A. Karande and L. G. Rathi

TABLE 3. Anti-inflammatory Activity of Synthesized Compounds 7a – 7l

Compound Dose (mg/kg,
Mean paw edema volume after houra % edema inhibition after hour
No. p.o.)

Control 10 mg/kg 0.188 ± 0.0098 0.348 ± 0.0098 0.598 ± 0.0098 0.658 ± 0.0098 – – – –

Indomethacin 1.5 0.101 ± 0.0098 0.16 ± 0.0063 0.221 ± 0.0040 0.275 ± 0.0054 46.01** 54.06** 62.95** 58.22**

7a 50 0.128 ± 0.0040 0.231 ± 0.0040 0.396 ± 0.0081 0.468 ± 0.0040 31.85 33.49 33.70 28.86

7b 50 0.161 ± 0.0098 0.218 ± 0.0075 0.331 ± 0.0075 0.418 ± 0.0075 14.15** 37.32** 44.56** 36.45**

7c 50 0.171 ± 0.0160 0.318 ± 0.0204 0.548 ± 0.0040 0.641 ± 0.0204 8.84 8.61 8.356 2.53

7d 50 0.156 ± 0.0051 0.260 ± 0.0063 0.4 ± 0.0063 0.53 ± 0.0063 16.81 25.35 33.14 19.49

7e 50 0.158 ± 0.0098 0.278 ± 0.0040 0.418 ± 0.0040 0.551 ± 0.0040 15.92 20.09 30.08 16.20

7f 50 0.175 ± 0.0054 0.295 ± 0.0083 0.445 ± 0.0054 0.5 ± 0.0063 7.07 15.31 25.62 24.05

7g 50 0.153 ± 0.0051 0.248 ± 0.0040 0.346 ± 0.0051 0.456 ± 0.0051 18.58** 28.70** 42.06** 30.63**

7h 50 0.150 ± 0.0089 0.258 ± 0.0098 0.338 ± 0.0032 0.441 ± 0.0036 20.35** 25.83** 43.39** 32.93**

7i 50 0.175 ± 0.0083 0.315 ± 0.0083 0.558 ± 0.0116 0.643 ± 0.0081 7.07 9.56 6.68 2.27

7j 50 0.148 ± 0.0040 0.228 ± 0.0040 0.356 ± 0.0081 0.476 ± 0.0081 21.23** 34.44** 40.38** 27.59**

7k 50 0.150 ± 0.0020 0.230 ± 0.0020 0.340 ± 0.0020 0.401 ± 0.0036 19.91** 33.73** 43.03** 39.01**

7l 50 0.140 ± 0.0012 0.200 ± 0.0016 0.290 ± 0.0012 0.371 ± 0.0024 25.39** 42.39** 51.44** 43.64**

a
Values are presented as mean ± S. E. M (n = 6); data were analyzed by one-way ANOVA followed by Dunnett’s multiple comparison tests.
** p < 0.01 compared to control group.

Flash chromatography was used for purification of synthe-
sized compound using a mixture of ethyl acetate and hexane
(1 : 1) as eluent. The flash chromatograph of 1-(4-fluorophe-
nyl)-2-{[5-(2-chlorophenyl)-4H-1,2,4-triazol-3-yl]sulfanyl}e
thanone 7l is shown in Fig. 1. The IR spectra of 2-{[5-(2-
chlorophenyl)-4H-1,2,4-triazol-3-yl]sulfanyl}-1-(substituted
phenyl)ethanones 7a – 7l showed in each case stretching
bands of NH, Ar-H and CH2 in the regions of 3500 – 3200,
3031 – 3097, and 2985.60 – 2833.24 cm–1, respectively. The
1
H-NMR spectra showed in each case the signal at
d = 7.94 – 7.17 ppm attributed to aromatic protons and at
d = 4.62 – 4.57 ppm due to CH2 protons. The siglet appeared
for NH of the triazole ring in the region of d = 10.77 –
10.57 ppm, integrating one proton. The 13C NMR spectra
showed in each case the carbon of C=O, and triazole ring dis-
played signals at d = 201.11 – 180.85 and 155.28 –
174.94 ppm. The aromatic and CH2 carbon resonated at
d = 163.93 – 112.86 and 56.69 – 44.35 ppm, respectively.
The elemental (CHNS) analyses were found within the limit
of theoretical values.
Anti-Inflammatory Studies
Anti-inflammatory activity data of compounds 7a – 7l
revealed that compound 7l exhibited excellent anti-inflam-
matory activity, while compounds 7b, 7g, 7h, 7j, and 7k
showed good anti-inflammatory activity as compared to that
of standard drug indomethacin. Compounds 7a, 7c, 7d, 7e,
7f, 7i showed lesser degree of activity.
CONCLUSION
We have synthesized a novel series of 2-{[5-(2-chloro-
phenyl)-4H-1,2,4-triazol-3-yl]sulfanyl}-1-(substituted phe-
nyl) ethanones 7a – 7l and studied their anti-inflammatory
activity. The obtained data show that compound 7l possesses
excellent anti-inflammatory activity. These results indicate
the necessity of fluoro substituent in the proposed system for
anti-inflammatory activity.
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