Generic placeholder image

Current Microwave Chemistry

Editor-in-Chief

ISSN (Print): 2213-3356
ISSN (Online): 2213-3364

Research Article

Microwave Assisted Green Synthesis of Benzimidazole Derivatives and Evaluation of Their Anticonvulsant Activity

Author(s): Biswa Mohan Sahoo*, Bimal Krishna Banik, Mazaharunnisa, Naidu Srinivasa Rao and Bodapati Raju

Volume 6, Issue 1, 2019

Page: [23 - 29] Pages: 7

DOI: 10.2174/2213335606666190429124745

Abstract

Background: Benzimidazole is the fused heterocyclic aromatic compound. It is an essential pharmacophore and privileged structure for the development of new drug molecules. These are bioactive molecules present in various anthelmintic drugs such as albendazole, mebendazole, parbendazole, triclabendazole etc.

Methods: Benzimidazole derivatives are synthesized by reaction between orthophenylene diamine and anthranillic acid followed by acetylation in the presence of acetic anhydride. Finally, the acetylated products undergo Claisen-Schimdt condensation with various substituted benzaldehydes to produce corresponding benzimidazole derivatives or chalcones. Both conventional and microwave irradiation technology are followed to get the titled compounds. The titled compounds are screened for their anticonvulsant and neurotoxicity activity.

Results: By the help of microwave synthesis, the yield of product was increased in less reaction time. So, it follows Green chemistry approach by making above reactions eco-friendly. Some of the compounds exhibited significant anticonvulsant activity as compared to standard drug.

Conclusion: In the present investigation, we have synthesized novel benzimdazole derivatives with chalone moiety to improve the biological activity. The compounds were obtained under microwave reaction with high yield in a short reaction time.

Keywords: Benzaldehydes, benzimidazole, chalcones, green synthesis, microwave, neurotoxicity, SAR study.

Graphical Abstract

[1]
Bansal, R.K. Heterocyclic chemistry: Chemistry and reaction of heterocyclic compound, 5th ed; New Age International Publisher, 2017.
[2]
Joule, J.A.; Mills, K. Heterocyclic Chemistry, 5th ed; Wiley-Blackwell Science: New York, 2000.
[3]
Gribble, G.W.; Gilchrist, T.L. Progress in Heterocyclic Chemistry., 1st ed. Elsevier. 14, 2002, https://www.elsevier.com/books/ progress-in-heterocyclic-chemistry/gribble/978-0-08-044190-0
[4]
Katritzky, A.R.; Boulton, J.A.; Lagowski, J.M. Advances in heterocyclic chemistry: Nomenclature of heterocyclic compounds, 1st ed; Academic Press: New York, 1963.
[5]
Shaharyar, M.; Mazumder, A. Benzimidazoles: A biologically active compounds. Arab. J. Chem., 2017, 10, S157-S173.
[6]
Eicher, T.H.; Hauptmann, S. The chemistry of heterocycles: Structure, reactions, syntheses, and applications, 2nd ed; Wiley-VCH, 2003.
[7]
Rangappa, S.K.; Hiremathad, A.; Budagumpi, S.; Nagaraja, B.M. Comprehensive review in current developments of Benzimidazole based medicinal chemistry. Chem. Biol. Drug Des., 2014, 86(1), 19-65.
[8]
Pathak, D.; Siddiqui, N.; Bhanupriya, B.; Ahsan, W.; Alam, S.M. Benzimidazoles: A new profile of biological activities. Der Pharm. Lett, 2010, 2(2), 27-34.
[9]
Singh, P.; Anand, A.; Kumar, V. Recent developments in biological activities of chalcones: A mini review. Eur. J. Med. Chem., 2014, 85, 758-777.
[10]
Zhuang, C.; Zhang, W.; Sheng, C.; Xing, C.; Miao, Z. Chalcone: A privileged structure in medicinal chemistry. Chem. Rev., 2017, 117(12), 7762-7810.
[11]
Yazdan, S.K.; Sagar, D.V.; Shaik, A.B. Chemical and biological potentials of Chalcones: A Review. Org. Med. Chem, 2015, 1(1), 1-8.
[12]
Kang, Y.H.; Pezzuto, J. Induction of Quinone reductase as a primary screen for natural product anti-carcinogens. Methods Enzymol., 2004, 382, 380-414.
[13]
Lidstrom, P. Microwave assisted organic: A review. Tetrahedron, 2001, 57(45), 9225-9283.
[14]
Ugwu, D. Synthesis and pharmacological applications of chalcones-A review. Int. J. Chem. Sci., 2015, 13(1), 459-500.
[15]
Chhonker, Y.S.; Veenu, B. Synthesis and pharmacological evaluation of some new 2-phenyl benzimidazoles derivatives and their Schiff’s bases. Eur. J. Chem., 2009, 6(1), 342-346.
[16]
Jubie, S.; Rajesh, K.R.; Yellareddy, B. Microwave assisted synthesis of some novel benzimidazole substituted fluoroquinolones and their antimicrobial evaluation. J. Pharm. Sci. Res., 2010, 2(2), 69-76.
[17]
Oztekin, A.; Kaessler, A. Comparative studies on conventional and microwave synthesis of some benzimidazole, benzothiazole and indole derivatives and testing on inhibition of hyaluronidase. Molecules, 2008, 13(4), 736-748.
[18]
Reddy, B.A. Synthesis, characterization and biological evaluation of 1,2-disubstituted benzimidazole derivatives using Mannich bases. Eur. J. Chem., 2010, 7(1), 222-226.
[19]
Ansari, K.F.; Lal, C. Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives. Eur. J. Med. Chem., 2009, 44(10), 4028-4033.
[20]
Rakesh, J.K.; Jawahar, J.L. Synthesis of Benzimidazole derivatives: As anti-hypertensive agents. Eur. J. Chem., 2006, 3(13), 278-285.
[21]
Sonwane, S.K.; Dua, R. Synthesis of some novel 2-azetidinone derivatives of 2-methylbenzimidazole by conventional and microwave assisted and evaluation of their antimicrobial efficacy. Der Pharma. Lett., 2010, 2(2), 159-167.
[22]
Singh, J.; Grover, P. Synthesis, anticonvulsant activity and comparative QSAR study of some novel 1,2,5-trisubstituted benzimidazole derivatives. Acta Pharm. Sci., 2010, 52, 511-522.
[23]
Krall, R.L.; Penry, J.K.; White, B.G.; Kupferberg, H.J.; Swinyard, E.A. Antiepileptic drug development: II. Anticonvulsant drug screening. Epilepsia, 1978, 19(4), 409-428.
[24]
Dunham, M.S.; Miya, T.A. A note on a simple apparatus for detecting neurological deficit in rats and mice. J. Am. Pharm. Assoc. (Sci Edit.), 1957, 46(3), 208-209.
[25]
Yadav, G.; Ganguly, S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. Eur. J. Med. Chem., 2015, 97, 419-443.

© 2024 Bentham Science Publishers | Privacy Policy