Medicinal Chemistry-Ii: 1.anti-Infective Agents: F

k.sathamhusian,r.rajesh,m.
senthilkumar Anthelmintics
professer.G.Rathinavel M.pharm
MEDICINAL
CHEMISTRY-II
1.Anti-infective agents:
F.ANTHELMINTICS:
Anthelmintics or anti-helminthics are a group of anti-
parasitic drugs that expel parasitic worm and other
internal parasites.
The term anthelmintic is restricted to drugs acting locally to expel
parasites from gastro intestinal tract. There are several types of worms
which penetrate other tissues, drugs which act on these parasitic
infections are also known as anthelmintics.The worm parasites of man
belong to two phyla: Nemathelminthes (roundworms) and
platyhelminthes (flatworms). The roundworms include hookworm,
whipworm, pinworm Strongyloides stercoralis, Trichinella spiralis and
Wuchereria bancrofti.
CLASSIFICATION
Anthelmintics are classified based upon their chemical structures.
1.Piperazines:: ex.. Diethylcarbamazine , Piperazine citrate.
2.Benzimidazoles: ex. Albendazole, Mebendazole, Thiabendazole.
3.Heterocyclics: ex. Oxamniquine, Praziquantel.
4.Natural products: ex. Ivermectin, Avermectin.
5. vinyl pyrimidines: ex. Pyrantel, Oxantel.
6.Amide: ex. Niclosamide .
MEDICINAL CHEMSISTRY-II Page 1

k.sathamhusian,r.rajesh,m.senthilkumar Anthelmintics
7.Nitro derivative: ex. Niridazole.

8.Imidazo thiazole: ex. Levamisole.
Example: (in chapter)

(*-means synthesis of drug)
Piperazinesalts(*)
DEC(Diethyl carbamazepine*)
Thiabendazole(*)
Mebendazole(*)
Albendazole
Niclosamide
Oxamniquine
Praziquantal and Ivermectin.
1.Piperazinesalts(*)
H
N O OH
O
O
HO OH
N OH
H
piperazine citrate
Piperazine other name called as hexahydropyrazine and

Diethylenediamine.
Synthesis:
The two molecules of aminoethanol converted as a
piperazine with loss of two molecules of
water.Afterpiperazine react with citric acid to form a
piperazinecitrate.Example of piperazine derivative
compound in the anthelmintics drug is called DEC(Diethyl
carbamazepine).
Step I:
H
NH2 HO N
+ + 2 H2O
N
OH H2N H
(2 molecules of aminoethanol) (piperazine) (water)
Step II:
H O OH H
N O N O OH
O O
O
+ HO OH . HO
OH OH
N N OH
H H
piperazine citric acid piperazine citrate
Uses:
It is used as an anthelminticsthe treatmentof round worm
(As carislumbricoids) and pin worm.
2.DEC:(Diethyl carbamazepine*)
Diethyl carbamazepine is a piperazine salt derivative
compound the chemical name is N,N-Diethyl-4-methyl
piperazine 1-carboxamide.it is a anthelmintic drug or anti-
helminthics or anti-parasitic drug.
Structure:
CH3
N O
CH3 CH3
IUPAC NAME:(N,N-Diethyl-4-methyl piperazine 1-

carboxamide)
Synthesis:
The methylpiperazine react with cobalt chloride(cocl2)
with loss of Hcl.After react with diethyl amine to form a

DEC(Diethyl carbamazepine in the chemical name is N,N-

Diethyl-4-methyl piperazine 1-carboxamide.
Step I:
CH3 CH3
N
N O
Cl
+ -HCL
Cl N
N
H
Cl O
methyl cobalt
chloride 1-methyl piperazine
piperazine
carbonyl chloride
Step II:
CH3
CH3
N
N CH3 heat
+ HN
-hcl N
N CH3
N O
Cl O
diethyl amine
1-methyl piperazine
carbonyl chloride CH3 CH3
diethyl carbamazipine
Uses:

It is effective against filariasis and tablets form as

cariasis.
.
3.Thiabendazole:(*)
Structure:
H
N S
N
N
Iupac name:
4-(1H-1,3-benzodiazole-2-yl)-1,3-thiazole
Synthesis:

N
Naclo N Cl
Alcl3 NH
N
+ NH N
S NH N
NH2
4-cyano aniline S
thiazole S
thiazole 4-iminomethane thiazole 4-iminomethane
phenyl amine phenyl amino chloride
H
Koh N N
N
Thiabendazole
Uses:
It is used as fungicide(fungal in orangefruits),parasiticide(hook worm
and round warm).
4.MEBENDAZOLE:(*)
Mebendazole is a benzimidazole derivative coumound.
Structure:
CH3
O O
H
N O
NH

IUPAC NAME:
Methyl(5 benzoyl-1,H-benzimidazol-2yl)carbamate.
Synthesis:
step 1: H
N
H HO O
N NH
NH2 + -HCOOH N O
O OH
HO
N
benzimidazole-2-amino
2-amino benzimidazole oxalic acid carboxilic acid
step 2: O H
N
Cl S Cl
H NH
N
NH
+ HO CH3
-water N O
O
N O (-H2O)
CH3
HO
benzimidazole methanol Methyl(1,H-benzimidazol-2
-2-aminocarboxilicacid
yl)carbamate.

O
H
step 3: O N
H
N NH
NH + Cl
-Hcl N O
O O
N
O CH3
CH3
Methyl(1,H-benzimidazol-2 benzoyl chloride Methyl

yl)carbamate. (5 benzoyl-1,H-benzimidazol-2yl)
carbamate
(Mebendazole)
USES:
It is highly effective broadspectrum antihelmintic indicate for the
treatement of nematode infestations including round warm,hook warm.
5.Albendazole:
Albendazole is a medication used for the treatment of a variety of
parasitic worm infestations.it is useful for pinworm disease ,hydatid
disease and ascariasis.it is a imidazole derivative compound.
Structure:
CH3
O
H
S N O
H3C
NH
Iupac name:
Methyl[5-(propylthio)-1H-benzimidazole-2-yl]carbamate
Uses:
1.it is effective first line of treatement
against(flatworms,tapeworm,nematodes,myiasis)
2.anti-protozoal agent.
6..NICLOSAMIDE:
O
+
N -
O O
Cl
NH
Cl
OH
IUPAC NAME:
5chloro-n-(2chloro-4-nitrophenyl)2-hydroxybenzamide.
USE:
1.It is a salicylamide compound. It is used as piscicide.
2.Treatment of warm infections.
3.It is used as treatment of tapeworms and not effective against other
worms.such as pinworms (or) roundworms.

7.OXAMINOQUINE:
HO
- CH3
O +
NH
N N
H
O CH3
IUPAC NAME:
1,2,3,4 tetrahydro-2-isopropylaminomethyl-7-nitro-6-quinolyl methanol.
USE:
It is used for treatment of schistomiasis.
It is equally effective as praziquanter for treating mansoni
infections
8.PRAZIQUANTEL:
O
N
N

IUPAC NAME:
2(cyclo hexyl carbonyl)1,3,6,7,-tetraahydro-pyrazino isoquinoline-4-
one.
USE:
1. It is used for the treatment of tapeworms and fakes.
2. It is used to disease caused by infection with several types of
internal/gastrointestinal and external parasites.
9.IVERMECTIN:(natural drug)
B1a:
H3C CH3
O CH3 CH3
HO O
O O
CH3
O H
O H C CH3
H3C O O 3
O O
H3C
OH
O CH3
H
OH
B1B:

H3C CH3
O CH3 CH3
HO O
O O CH3
O H
O H C CH3
H3C O O 3
O O
H3C
OH
O CH3
H
OH
IUPAC NAME:
1.( 22,23 dihydroavermectin) b1a AND 2.(22,23 dihydroavermectin )
B1b.
USE:
It is used to treat head
lice,scabies,riverblindness,strongyloidiasis,lymphaticfilariasis.
It is also used to treatment of onchoceriasis.it is a natural drug
isolated from natural sources.


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k.sathamhusian,r.rajesh,m.

MEDICINAL CHEMSISTRY-II Page 1

7.Nitro derivative: ex. Niridazole.

Example: (in chapter)

Piperazine other name called as hexahydropyrazine and

(2 molecules of aminoethanol) (piperazine) (water)

IUPAC NAME:(N,N-Diethyl-4-methyl piperazine 1-

MEDICINAL CHEMSISTRY-II Page 4

DEC(Diethyl carbamazepine in the chemical name is N,N-

MEDICINAL CHEMSISTRY-II Page 5

It is effective against filariasis and tablets form as

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Methyl(1,H-benzimidazol-2 benzoyl chloride Methyl

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