Biology and Chemistry of Benzimidazole Derivatives as Antiulcer Agents: A Review
Subject Areas : Journal of Chemical Health Risks
Geeta Yadav
1
(
Department of Pharmacy, Chandigarh Pharmacy College (CPC), Chandigarh Group of Colleges- CGC, Jhanjeri, Punjab-140307, India
)
Keywords: Benzimidazole, Imidazole, Heterocyclic, Proton pump inhibitors, Clinical drugs,
Abstract :
A flexible heterocyclic moiety found in many synthetic and natural compounds is benzimidazole. Because of its wide-ranging effects, it has drawn interest from researchers all around the world for the treatment of many illnesses. Many proton pump inhibitors that have received clinical approval have been available in the market since the discovery of Omeprazole in 1988, which was the first inhibitor based on benzimidazole. But the primary focus of research is on the necessity of pursuing specific goals in order to lessen the adverse effects of proton pump inhibitors. In order to achieve these goals, numerous different proton pump inhibitor medication combinations have also been tested. At the moment, clinical trials are being conducted on a few novel and inventive formulations. In order to set the stage for future investigations, a thorough analysis of antiulcer benzimidazoles was conducted. Researchers and academicians would find this review paper useful in their efforts to create less hazardous and more therapeutically active benzimidazoles. To the best of our knowledge, this study is the first attempt to compile important developments on benzimidazoles that have been suggested as antiulcer drugs.
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2. Brink N.G., Flokers K., 1949. Vitamin B12. vi. 5,6-dimethylbenzimidazole, a degradation product of vitamin B12. J Am Chem Soc. 71, 2951.
3. Emerson G., Brink N.G., Holly F.W., Koniuszy F., 1950. Vitamin B12. VIII. Vitamin B12-Like Activity of 5,6-Dimethylbenzimidazole and Tests on Related Compounds. J Am Chem Soc. 72, 3084.
4. Jerchel D., Fischer H., Fracht M., 1952. Zur Darstellung der Benzimidazole. Liebigs Ann Chem. 575, 162-173.
5. Raj S, Barnali M., Balamurali M., 2017. Synthesis and Medicinal Applications of Benzimidazoles: An Overview. Curr Org. Syn. 14, 40-60.
6. Alaqeel S.I., 2017. Synthetic approaches to benzimidazoles from o-phenylenediamine: A literature review. J Saudi Chem Soc. 21, 229-237.
7. Salahuddin,. Shaharyar M., Mazumder A., 2017. Benzimidazoles: A biologically active compounds. Arabian J Chem. 10, S157-S173.
8. Song D., Ma S., 2016. Recent Development of Benzimidazole-Containing Antibacterial Agents. Chem Med Chem. 11(7), 646-59.
9. Keri R.S., Hiremathad A., Budagumpi S., Nagaraja B.M., 2015. Comprehensive Review in Current Developments of Benzimidazole-Based Medicinal Chemistry. Chem Biol Drug Des. 86, 19–65.
10. Yadav G., Ganguly S., 2015. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. Eur J Med Chem. 97, 419-443.
11.Fei F., Zhou Z., 2013. New substituted benzimidazole derivatives: a patent review (2010 – 2012). Expert Opin Ther Pat. 23(9),1157-79.
12. BarotK.P., Nikolova S., Ivanov I., Ghate D., Manjunath., 2013. Novel Research Strategies of Benzimidazole Derivatives: A Review. Mini Rev Med Chem. 13(10), 1421-47.
13. Snowden F.M., 2008. Emerging and reemerging diseases: ahistorical perspective. Immunol.Rev.225, 9-26.
14. Wang H., Naghavi M., Allen C., Barber R.M., Bhutta Z.A., Carter A., Casey D.C., Charlson F.J., Chen, A.Z., Coates M.M. and Coggeshall, M., 2016. Global, regional, and national life expectancy, all-cause mortality, and cause-specific mortality for 249 causes of death, 1980–2015: a systematic analysis for the Global Burden of Disease Study 2015. The lancet. 388(10053), 1459-1544.
15. Wang A.Y., Peura D.A., 2011. The prevalence and incidence of Helicobacter pylori–associated peptic ulcer disease and upper gastrointestinal bleeding throughout the world. Gastrointestinal Endoscopy Clinics. 21(4), 613-635.
16. Marshall B., Warren J.R., Blincow E., Phillips M., Goodwin C.S., Murray R., Blackbourn S., Waters T. and Sanderson C., 1988. Prospective double-blind trial of duodenal ulcer relapse after eradication of Campylobacter pylori. The Lancet. 332(8626-8627), 1437-1442.
17. Marshall B.J., Warren J.R., 1984. Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration. Lancet. 323, 1311–1315.
18. Malfertheiner P., Megraud F., O'Morain C.A., Atherton J., Axon A.T., Bazzoli F., Gensini G.F., Gisbert J.P., Graham D.Y., Rokkas T. and El-Omar E.M., 2012. Management of Helicobacter pylori infection—the Maastricht IV/Florence consensus report. Gut. 61(5), 646-664.
19. Yuan Y., Ford A.C., Khan K.J., Gisbert J.P., Forman D., Leontiadis G.I., Tse F., Calvet X., Fallone C., Fischbach L., Oderda G., 2013. Optimum duration of regimens for Helicobacter pylori eradication. Cochrane Database of Systematic Reviews. 11(12), CD008337.
20. Robert S., McDonald I.M., Burger’s Medicinal Chemistry & Drug Discovery, 6thed., John Wiley and Sons, New Jersey, 2003, pp.86-121.
21. Lindberg P., Nordberg P., Alminger T., Braendstroem A., Wallmark, B., 1986. The mechanism of action of the antisecretory agent omeprazole. Journal of Medicinal Chemistry. 29(8), 1327-1329.
22. Sachs G., Shin J.M., Briving C., Wallmark B., Hersey S., 1995. The pharmacology of the gastric acid pump: the H+, K+ ATPase. Annual Review of Pharmacology and Toxicology. 35(1), 277-305.
23. Ife R.J., Dyke C.A., Keeling D.J., Meenan E., Meeson M.L., Parsons M.E., Price C.A., Theobald C.J., Underwood, A.H., 1989. 2-[[(4-Amino-2-pyridyl) methyl] sulfinyl] benzimidazole H+/K+-ATPase inhibitors. The relationship between pyridine basicity, stability, and activity. Journal of medicinal chemistry. 32(8), 1970-1977.
24. Shin J.M., Cho Y.M., Sachs, G., 2004. Chemistry of covalent inhibition of the gastric (H+, K+)-ATPase by proton pump inhibitors. Journal of the American Chemical Society. 126(25), 7800-7811.
25. Besancon M., Shin J.M., Mercier F., Munson K., Miller M., Hersey, Sachs, G., 1993. Membrane topology and omeprazole labeling of the gastric hydrogen ion-potassium-adenosinetriphosphatase. Biochemistry. 32(9), 2345-2355.
26. Shin J.M., Homerin M., Domagala F., Ficheux H., Sachs, G., 2006. Characterization of the inhibitory activity of tenatoprazole on the gastric H+, K+-ATPase in vitro and in vivo. Biochemical pharmacology. 71(6), 837-849.
27. Stedman C.A.M., Barclay M.L., 2000. Comparison of the pharmacokinetics, acid suppression and efficacy of proton pump inhibitors. Alimentary Pharmacology & Therapeutics. 14(8), 963-978.
28. Sachs G., 2003. Physiology of the parietal cell and therapeutic implications. Pharmacotherapy: The Journal of Human Pharmacology and Drug Therapy. 23(10P2), 68S - 73S.
29. Sachs G., 2001. Improving on PPI-based therapy of GORD. Eur J Gastroenterol Hepatol. 13 (Suppl. 1), S35–41.
30. Sih J.C., bin Im W., Robert A., Graber D.R., Blakeman, D.P., 1991. Studies on (H+/K+)-ATPase inhibitors of gastric acid secretion. Prodrugs of 2-[(2-pyridinylmethyl) sulfinyl] benzimidazole proton-pump inhibitors. Journal of Medicinal Chemistry. 34(3), 1049-1062.
31. Seth S.D., Text Book of Pharmacology, 2nd ed., Elsevier: New Delhi, 1999, pp. 390- 391.
32. Wright, J.B., 1951. The chemistry of the benzimidazoles. Chemical Reviews. 48(3), 397-541.
33. Leeson P.D., Baker R., Carling R.W., Curtis N.R., Moore K.W., Williams B.J., Foster A.C., Donald A.E., Kemp J.A., Marshall G.R., 1991. Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor. J Med Chem. 34, 1243-1252
34. Louvet P., Lallement G., Pernot-Marino I., Luu-Duc C., Blanchet G., 1993. Novel benzimidazoles as ligands for the strychnine-insensitive N-methyl-d-aspartate-linked glycine receptor. European Journal of Medicinal Chemistry. 28(1), 71-75.
35.Berger M.L., Schödl C., Noe C.R., 1996. Benzimidazole‐type Glycine Antagonists: The Role of the Ring Nitrogen Atoms. Archive der Pharmazie. 329(3), 121-124.
36. Ingle R.G., Magar D.D., 2011. Heterocyclic chemistry of Benzimidazoles and potential activities of derivatives. Int J Drug Res Technol. 1(1), 26-32.
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