Synthesis Of Some New Benzimidazole Acetic Acid Derivatives And Evaluation For Their Antimicrobial And Antitubercular Activities
Substituted benzimidazole have received considerable attention during last few decades as they are endowed with variety of biological activities and have wide range of therapeutic properties. A literature survey indicates that benzimidazole derivatives possess different biological activities such as anti-microbial activity, anti-ulcer ,antiparasitic, antiprotozoal , antiviral and antitubercular.
Physical properties shown that, Benzimidazoles have high melting points, Benzimidazoles are usually soluble in polar solvents and sparingly soluble in non polar solvent,Benzimidazoles are weakly basic, being some what less basic than imidazole, Benzimidazoles are also sufficiently acidic to be generally soluble in aqueous alkali . The acidic properties of benzimidazoles, like those of imidazole, seem to be due to stabilization of the ion by resonance. The pKa value of benzimidazoles (pKa=5.30)
A new series of benzimidazoles acetic acid derivatives were synthesized by reacting 2(2-substituted phenyl ethenyl) 1H benzimidazole with chloroacetic acid under reflux. The structures of these compounds were established by means of IR, 1H-NMR, 13C-NMR and elemental analysis. All compounds were evaluated for antibacterial, antifungal and antitubercular activities.
Most of the compounds have shown significant antibacterial, antifungal and antitubercular activity when compared with the standard drug Stryptomycin.
Jadhav G.R.,Shaikh M.V.,Kale R.P. et.al. SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents . Eur.j. med. Chem.2008:1-16.
Tripathi KD. Essential of Medical Pharmacology 5th edition, Jaypee publishers. New Delhi 2003:698 – 699.
Rajendra Prasad, “Management of Multi-Drug Resistant Tuberculosis:
Practitioner's view point.” Ind J Tuber.,2007; 54: 3-11.
Yadav R, Srivastava SD, Srivastava SK., Synthesis antimicrobial and anti-inflammatory activities of 4-oxothiazolidines and their 5-arylidines. Ind. J. Chem, 2005; 44(B): 1262-1266.
Fatma E.Goda, Atif S, et.al. Synthesis, biological evaluation and molecular modeling investigation of new benzimidazole analogs as antiviral agents.Saudi pharm.journal. 2008;16:103-111
A R Prasad, A Narashima Rao, fused thiazoles: synthesis and antifungal activity of 2-arylidene-thiazolo [3’,2’:1,2]imidazo[5,4-b] pyrindin-3(2H)-ones, 2-arylidenethiazolo-[3,2-a] benzimidazol-3(2H)-ones and 6-arylidenethiazolo[3,2-b]-s-triazol-5(6H)-ones. Ind. j.chem.1986; 25 B:776-778.
Agarwal Alka, Agarwal Shiv K., Bhankuni D. S. antiparasitic agents: Part XVI –synthesis of 5(6)-substituted benzimidazole-2-carbamates as anthelminitic agents.Ind J. Chem, 1993;32B: 413-456.
A. L. Barry, “The antimicrobial susceptibility test: principle & practices”, edited by IIIus Leu & Febiger, Philadelphia, Pa. USA, 180; Biol. Abstr; 64, 1976, 25783.
Elmer W K, Stephen D A, William M J, Paul C S, Washing Jr C W, Text Book of Diagnostic Microbiology, 5th ed; Lippincot- publishers; 2002.
Agrawal RK, Sharma S., A new synthesis of substituted benzimidazole-2-ones. Ind. J. Chem, 1982; 21 (b): 967-968.
Vijayender KR, Mogilaiah K, Sreenivasulu B., Synthesis of 2-(2-amino-2-pyridyl) benzimidazoles. Ind. J. Chem, 1984; 23 (B): 866-867.
Katoch V.M. New generation methods for drug susceptibility testing for tuberculosis Ind. J.Tuberc.2008;55:61-63.
Burger A et. al., Comprehensive Medicinal Chemistry. 1990; 23:22.
Camille, G.Wermuth. The Practice of Medicinal Chemistry. Elsevier. 2001; 2: 29.
Martin, Y.C et. al., Modern Drug Research, Paths to Better and Safer Drugs, ed 5, New York, 1989: 243-73.
Lindberg, P. and Mitscher, L. A. European Journal of Medicinal Chemistry. 1998; 6: 243-73.
John B Wright et. al. The chemistry of benzimidazoles. Chemical Reviews. 1951; 3 (3):397-541.
. Day AR. Electronic mechanism of organic synthesis. 1951; 2: 242-243.
Preston PN. Synthesis Reactions and Spectroscopic properties of benzimidazoles.
Chemical Reviews. 1974; 15 : 279-314
Shriner RL and Robert W Upson. Synthesis of bis-benzimidazoles from diabasic
acids.Journal of Organic Chemistry. 1941; 63(8) : 2277
E.C. S. Krieg, N. R. In Micorobiology, , ed 5, Tata McGrawHill Publication, 1986:
Kokare, C. C. In Pharmaceutical Microbiology, ed 4, Nirali Prakashan, 2007, pp 1.1-
11, 2.1- 2.11.
Robert Fd.Wilson and Gisvold`s Text book of organic medicinal and pharmaceutical
chemistry, ed 8, j b Lippincott company,Philadelphia, 1996: 354-375.
Goodman Gilman, Alfred and McGraw-Hill, The Pharmacological Basis of
Therapeutics, edMcGraw-Hill Medical Publishing Division, 2001, pp 1284.
Fromtling R A, Recent Trends in the Discovery, Development and Evaluation of
Antifungal Agents, ed 7, Prous Barcelona, 1987:12-25.
Sung yun cho et. al., Synthesis and SAR of benzimidazole derivatives containing
oxycyclic and pyridine as a gastric H+-K+-ATPase inhibitors. Bull Kor Chemical
Society. 2001; 22: 1217-1223.
Kubo K et. al., Synthesis of 2-[ [ 4- fluroalkoxy -2-pyridyl] methyl] sulfinyl] –
Hbenzimidazole as anti-ulcer agents. Chem Pharma Bull. 1900; 38: 2853-2858.
Dunn GL et. al., Anti parasitic agents I 2-(nitroheterocyclic) benzimidazoles,
benzoxazoles and benzthiazoles. Journal of Medicinal Chemistr. 1966; 9: 751-75.
Gualtiere F et. al., Benzothiazoles and benzoxazole analogues of 2-(α-
hydroxybenzyl) benzimidazole. Journal of Medicinal Chemistry. 1971; 14: 546-549.
Ramesh Dhani et al. Reactivity Of Novel Substituted Benzimidazole Derivatives
IJAPN. 2011 July – Sept. 1(3) : 114 – 120.
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