*Corresponding Author Address: B. Vishwanathan, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS
University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India; E-mail: vishwanathan_b@yahoo.co.in
World Journal of Pharmaceutical Sciences
ISSN (Print): 2321-3310; ISSN (Online): 2321-3086
Published by Atom and Cell Publishers © All Rights Reserved
Available online at: http://www.wjpsonline.org/
Original Article
Anticoagulant evaluation of 1,3,4-oxadiazole derivatives derived from benzimidazole
B. Vishwanathan*and B.M. Gurupadayya
Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara
Nagar, Mysore, Karnataka-570 015, India
Received: 22-11-2014 / Revised: 31-12-2014 / Accepted: 02-01-2015
Abstract
In the present study, a series of 1,3,4-oxadiazole derivatives (4a-4k) derived from benzimidazole were evaluated
for ex vivo anticoagulant activity. The anticoagulant study was performed for increase in prothrombin time (PT)
and activated partial thromboplastin time (aPTT) at a test dose of 25 mg kg
-1
. The results of ex vivo
anticoagulant evaluation revealed that the tested compounds 4a-4k exhibited moderate increase in PT with
respect to acenocoumarol (1 mg kg
-1
) employed as reference drug for increase in PT. While the compounds 4a-
4k exhibited minimal increase in aPTT in comparison to unfractionated heparin (500 IU kg
-1
) employed as
reference drug for increase in aPTT. Compounds, 4c, 4b and 4k exhibited substantial anticoagulant activity with
increase in PT 32 ± 0.7, 36 ± 0.5 and 41 ± 0.4 s, respectively to that of the reference drug acenocoumarol (48 ±
0.5 s).
Keywords: 1,3,4-Oxadiazole; Activated Partial Thromboplastin Time; Benzimidazole; Prothrombin Time.
INTRODUCTION
The lacunae in present medication for management
of arterial thromboembolism (ATE) disorders by
anticoagulant therapy are having recurrent ATE
episodes. ATE is the most common cause of
cardioembolic events including myocardial
infarction, ischemic stroke, and limb gangrene.
ATE is currently the leading cause of death and
illness in developed countries, principal causes of
morbidity and mortality world-wide.[1] Clinical
studies highlight that anticoagulants are the drugs
of choice for the prevention and treatment of ATE
disorders, and prophylaxis of thrombotic events in
both pre- and post-surgery in clinical practices.[2]
Warfarin, acenocoumarol and phenprocoumon
which are the major 4-hydroxycoumarin
derivatives presently available in clinical use as
oral anticoagulants have been the core of
anticoagulantion therapy for more than two
decades.[3] Generally known as antivitamin K,
pharmacological 4-hydroxycoumarin
anticoagulants are vitamin K epoxide reductase
(VKOR) inhibitors. Vitamin K is converted to its
active form by the enzyme VKOR and recycled to
vitamin K 2,3-epoxide to maintain the coagulation
cycle.[4] 4-hydroxycoumarin derivatives like
warfarin, acenocoumarol and phenprocoumon
antagonize VKOR, thus preventing vitamin K
recycling and resulting in an accumulation of
abnormal form of coagulation protein, known as
proteins induced by vitamin K antagonism or des-
Ȗ-carboxyprothrombin leading to inhibition of the
coagulation process. The narrow therapeutic index
and other major clinical drawbacks like drug-drug
interaction, food-drug interaction, purple toe
syndrome, eclampsia, risk of haemorrhage etc., call
for continuous therapeutic drug monitoring for 4-
hydroxycoumarin anticoagulants. These entire
therapeutic shortcomings indicate the need for
better anticoagulant agents with clinical advantage.
In our previous study, we had reported the
synthesis and characterization of 1,3,4-oxadiaozle
derivatives 4a-4k (Fig. 1), from (1H-
benzo[d]imidazol-2-yl)methanamine.[5] Wherein,
N-[(1H-benzo[d]imidazol-2-yl)methyl](5-
substituted-1,3,4-oxadiazol-2-yl)methanamine; 4a-
4j (Table 1) were prepared by nucleophilic addition
of aryl/heteroaryl/aliphatic carboxylic acids with 2-
[(1H-benzo[d]imidazol-2-yl) methylamino]
acetohydrazide in presence of phosphorous
oxychloride. The acetohydrazide derivative was
prepared by condensation of ethyl 2-[(1H-
benzo[d]imidazol-2-yl)methylamino]acetate with
hydrazine monohydrate. The ester derivative was
prepared by N-alkylation of (1H-benzo[d]imidazol-
2-yl)methanamine with ethyl 2-chloroacetate in the
presence of anhydrous potassium carbonate. The