Design; Synthesis and Antihypertensive activity of 4'-(2-{2-[(2-chlorobenzylidene)-amino]-phenyl}-5-nitro-benzoimidazol-1-ylmethyl)] biphenyl-2-carboxylic acid
Keywords:
Benzimidazoles, biphenyl-2-carboxylic acid, angiotensin II, hypertensionAbstract
In the present study, a series of 4`-(2-{2-[(2-chloro-benzylidene)- amino]-phenyl}-5-nitro-benzoimidazol-1-ylmethyl)] biphenyl-2- carboxylic acid derivatives are synthesized by A one-step coupling of substituted benzimidazoles with biphenyl carboxylic moiety mediated by potassium carbonate is described. The biphenyl carboxylic moiety was prepared from 9-H-fluorenone and substituted benzimidazoles were synthesized from ophenylenediamine with anthranilic acid.
References
Goodman G, The Pharmacological Basis
of Therapeutics, 7th Ed., McGraw-Hill,
New York ed., 1985, pp.639–659.
Juillerat J.L, Celerier J, Chapuis B.C,
Nguyen G, Wostle W, Maerki H.P, Janzer
R.C. Rennin and angiotensinogen
expression and functions in growth and
apoptosis of human glioblastoma. Br J
Cancer 2004; 90: 1059-1068.
FogartyD.J, Sanchez-Gomez M.V, Matute
C. Multiple angiotensin receptor subtype
in normal and tumor astrocyte in vitro.
Glia 2002;39: 304-314.
Tiziano T, Vincenzo C, Simona R,
Adriano M. Proposal of a new binding
orientation for non-peptide ATI
antagonists: Homology modeling, docking
and three dimensional quantitative
structure-activity relationship analysis. J
Med Chem 2006;49: 4305-4316.
Wong PC, Barnes TB, Chiu AT. Losartan
(DuP 753), an Orally Active Nonpeptide
Angiotensin II Receptor Antagonist.
Cardiovasc Drug Rev 1991; 9: 317-319.
Bali A, Bansal Y, Sugumaran M, Saggu
J.S, Balakumar P, Kaur G, Bansal G,
Sharma A, Singh M. Design, synthesis and
evaluation of novelly substituted
benzimidazole compounds as angiotensin
II receptor antagonists. Bioorg Med Chem
Lett 2005;15,3962-3965.
Jat R.K,Jat J.L, Pathak D.P.Synthesis of
Benzimidazole Derivatives: As Antihypertensive Agents.E Journal of
Chemistry 2006;3:(13), 278-285.
Dhvanit I. S, Sharma M, Bansal Y,Bansal
G, M. Singh. Angiotensin II AT1 receptor
antagonists: Design, synthesis and
evaluation of substituted carboxamido
benzimidazole derivatives European
Journal of Medicinal Chemistry 2008;43,
-1812.
Badyal D.K, Lata H, Dadhich A.P.Indian J
of Pharmacology 2003; 35(66), 349-362.
Bunag R.D, McCubbin J.W, Page I.H.
Lack of correlation between direct and
indirect measurements of arterial pressure
in unanaesthetized rats. Cardiovasc Res
;5(1): 24-31.
Gupta S.K.Drug Screening methods,
Jaypee Brothers Medical Publisher, New
Delhi,2004; pp 236-246.
Shreenivas M.T, Chetan B.P, Bhat A.R,
Synthesis and Pharmacological Evaluation
of Certain Schiff Bases and Thiazoldine
Derivatives as AT1 Angiotension-II (AII)
Receptor Antagonists. Journal of
Pharmaceutical Science and Technology
; 1 (2), 88-94.
Fieser M, Fieser L. Reagents for organic
synthesis 1969; 2, pp. 389.
Saggu J.S, Sharma R,Dureja H,Kumar V.
Benzimidazoles with biphenyls: Synthesis
of 5-substituted-2-npropyl- 1-[(2’-
carboxybiphenyl-4-yl-) methyl]
benzimidazoles. J Indian Inst Sci 2002;82,
–182.