Cyclization Reactions for Synthesis of Benzthiazole- A Review

Authors

  • Praul Singh Advance Institute of Biotech and Paramedical Sciences, Naramau, Kanpur.
  • Ashish Srivastava Pranveer Singh Institute of Technology, Bhauti, Kanpur.
  • Abhinav Prasoon Mishra Pranveer Singh Institute of Technology, Bhauti, Kanpur.
  • Reena Mehtab Pranveer Singh Institute of Technology, Bhauti, Kanpur.

Keywords:

Benzothiazole, Cyclization, Catalysts

Abstract

Benzoheterocycles such as benzothiazoles can serve as unique and versatile scaffolds for experimental drug design. Among the all benzoheterocycles, benzothiazole has considerable place in research area especially in synthetic as well as in pharmaceutical chemistry because of its potent and significant pharmacological activities. Various benzothiazoles such as 2-aryl benzothiazole received much attention due to unique structure. Development of combination of 2- aminobenzothiazoles with other heterocyclic is a well known approach to design new drug like molecules, which allows achieving new pharmacological profile, action, toxicity lowering. In this review, we discussed various methods to synthesize as well as cyclization of benzothiazole derivatives and various structural alterations conducted on benzothiazole ring and preferential specificities imparted in their biological responses.

References

1. Bose, D.S., Idrees, M., 2007. A convenient access to substituted benzothiazole scaffolds via intramolecular
cyclization of thioformanilides. Tetrahedron Letters., vol. 48, pp. 669–672.
2. Carolina, B., Fernando, B., Pedro, U., Elena, F., Carmen, C., Sergio, C., 2003. Synthesis of 2 substituted benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides. Tetrahedron Letters., vol. 44, pp. 6073–6077.
3. Chandrappa S., Vinaya, K., Muddegowda, U., Kanchugarakoppal, S.R., 2011. One-pot approach
for the synthesis of 2-aryl benzothiazoles via a twocomponent coupling of gem-dibromomethylarenes and o-aminothiophenols. Tetrahedron Letters., vol.52, pp. 5474–5477.
4. Chaudhary, P., Sharma, P. K., Sharma, A., Varshney, Jonish., 2010. Recent advances in pharmacological
activity of benzothiazole derivatives. International Journal of Current Pharmaceutical Research., vol. 2,
issue 4, pp. 5-11.
5. Gupta, A., Rawat, S., 2010. Synthesis and Cyclization of Benzothiazole: Review. Journal of Current Pharmaceutical Research ., vol.3, issue 1, pp. 13-23.
6. Gupta, S., Ajmera, N., Gautam, N., Sharma, R., Gauatam, D., 2009. Novel synthesis and biological activity study
of pyrimido [2,1-b] benzothiazoles. Ind J Chem., vol.13 issue 48B, pp. 853-858.
7. Heo, Y., Song, Y., Kim, B., Heo, J., 2006. A highly regioselective synthesis of 2-aryl-6- chlorobenzothiazoles employing microwave-promoted Suzuki-Miyaura coupling reaction. Tetrahedron Letters., vol.47, pp. 3091-3094.
8. Hutchinson, I., Chua, M.S., Browne, H.L., Trapani, V. Bradshaw, T.D., Westwell, A.D., 2001.Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl) benzothiazole Amino Acid Prodrugs. J Med Chem., vol.44, pp. 1446-1449.
9. Jaseer, E.A., Prasad, D.J.C., Dandapat, A., Sekar, G., 2010. An efficient copper (II)-catalyzed synthesis of
benzothiazoles through intramolecular couplingcyclization of N-(2-chlorophenyl) benzothioamides. Tetrahedron Letters., vol.51, pp. 5009–5012.
10. Khokra, S.L., Arora, K., Mehta, H., Aggarwal, A., Yadav, M., 2011. Common Methods to Synthesize Benzothiazole Derivatives and Their Medicinal Significance. International Journal of Pharmaceutical Sciences and Research., vol.2, issue 6, pp. 1356-1377.
11. Kini, S., Swain, S., Gandhi, A., 2007. Synthesis and Evaluation of novel Benzothiazole Derivates against
Human Cervical Cancer cell lines. Ind J Pharm Sci., pp. 46-50.
12. Kumbhare, R.M., Ingle, V.N., 2009. Synthesis of novel benzothiozole and benzisoxazole functionalized
unsymmetrical alkanes and study of their antimicrobial activity. Ind J Chem., issue 48B, pp. 996-1000.
13. Maharan, M., William, S., Ramzy, F., Sembel, A., 2007. Synthesis and in vitro Evaluation of new benzothiazolederivaties as schistosomicidal agents. Molecules., vol.12, pp. 622-633.
14. Murthi, Y., Pathak, D., 2008. Synthesis and Antimicrobial screening of Substituted 2-Mercaptobenzothiazoles. J
Pharm Res., vol.7, issue 3, pp. 153-155.
15. Paramashivappa, R., Phanikumar, P., Subbarao, P., Srinivasarao, A., 2003. Design synthesis and biological
evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors.
Bioorg Med Chem Lett., vol.13, pp. 657-660.
16. Rajeeva, B., Srinivasulu, N., Shantakumar, S., 2009. Synthesis and Antimicrobial activity of some new
2-substituted benzothiazole derivatives. E-Journal of Chemistry., vol.6, issue 3, pp. 775-779.
17. Reddy, P., Lin, Y., Chang, H., 2007. Synthesis of novel benzothiazole compounds with an extended conjugated
system. Arcivoc., vol. 16, pp. 113-122.
18. Shivaraj, H., Gazi, S., Patil, S., Surwas, S., 2010. Synthesis and biological evaluation of some benzothiazole
derivatives. Asian J Research Chem., vol. 3, issue 2, pp. 421-427.
19. Shukla, J., Hazra, K., Rashmi, P., Nargund, L.V.G., 2011. Synthesis and antibacterial activity of some novel
fluorobenzothiazole derivatives. Pelagia Research Library Der Chemica Sinica., vol.2, issue 3, pp. 4-10.
20. Stanton, H.L.K., Gambari, R., Chung, H.C., Johny, C.O.T., Filly, C., Albert, S.C.C., 2008. Synthesis and anti-cancer
activity of benzothiazole containing phthalimide on human carcinoma cell lines. Bioorg Med Chem., vol.16,
pp. 3626-3631.
21. Umesh, R.P., Jyotirling, R.M., Dhanaji, V.J., Ramrao, A.M.J., 2009. Bakers’ yeast catalyzed synthesis of
benzothiazoles in an organic medium. Tetrahedron Letters., vol.50, pp. 1352-1354.
22. Wang, M., Gao. M., Mock, B., Miller, K., Sledge, G., Hutchins, G., Zheng, Q., 2006. Synthesis of C-11 labelled
fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agent. Bioorg Med Chem., vol.14,
pp. 8599-8607.
23. Xue-Jun, M., Jian-Ping, Z., Run-Sheng, Z., Jun-Chen, W., 2005. Mn(III)-Promoted cyclization of substituted thioformanilides under microwave irradiation: a new reagent for 2-substituted benzothiazoles. Tetrahedron
Letters., vol.46, pp. 4345–4347.

Downloads

Published

2018-10-26

How to Cite

Singh, P., Srivastava, A., Mishra, A. P., & Mehtab, R. (2018). Cyclization Reactions for Synthesis of Benzthiazole- A Review. Journal of Drug Discovery and Development ( ISSN:2581-6861), 1(1), 4-12. Retrieved from http://medicaljournalshouse.com/index.php/JDrug-Discovery-Development/article/view/48

Issue

Vol. 1 No. 1 (2017): Journal of Drug Discovery and Development

Section

Articles

License

We, the undersigned, give an undertaking to the following effect with regard to our article entitled
“_______________________________________________________________________________________________________________________________________________________________________________
________________________________________________________________________________” submitted for publication in (Journal title)________________________________________________ _______________________________________________________Vol.________, Year _________:-

1. The article mentioned above has not been published or submitted to or accepted for publication in any form, in any other journal.

2. We also vouchsafe that the authorship of this article will not be contested by anyone whose name(s) is/are not listed by us here.

3. I/We declare that I/We contributed significantly towards the research study i.e., (a) conception, design and/or analysis and interpretation of data and to (b) drafting the article or revising it critically for important intellectual content and on (c) final approval of the version to be published.

4. I/We hereby acknowledge ADRs conflict of interest policy requirement to scrupulously avoid direct and indirect conflicts of interest and, accordingly, hereby agree to promptly inform the editor or editor's designee of any business, commercial, or other proprietary support, relationships, or interests that I/We may have which relate directly or indirectly to the subject of the work.

5. I/We also agree to the authorship of the article in the following sequence:-

Authors' Names (in sequence) Signature of Authors
1. _____________________________________ _____________________________________
2. _____________________________________ _____________________________________
3. _____________________________________ _____________________________________
4. _____________________________________ _____________________________________
5. _____________________________________ _____________________________________
6. _____________________________________ _____________________________________
7. _____________________________________ _____________________________________
8. _____________________________________ _____________________________________

Important

(I). All the authors are required to sign independently in this form in the sequence given above. In case an author has left the institution/ country and whose whereabouts are not known, the senior author may sign on his/ her behalf taking the responsibility.

(ii). No addition/ deletion/ or any change in the sequence of the authorship will be permissible at a later stage, without valid reasons and permission of the Editor.

(iii). If the authorship is contested at any stage, the article will be either returned or will not be
processed for publication till the issue is solved.