DESIGN, SYNTHESIS AND ANTIMICROBIAL EVALUATION OF SOME MANNICH BASE DERIVATIVE OF 2-(SUBTITUTED)-5-AMINO-THIADIAZOLES

  • K Balaji GITAM University
  • Priyanka Bhatt GITAM University
  • D. Mallika GITAM University
  • Anjali Jha Department of Chemistry, GIS, GITAM University, Rushikonda, Visakhapatnam, 530045, India

Abstract

Objective: The major objective of the present study was to design, synthesize some Mannich base derivative of 2-substituted-5-amino thiadiazoles with primary amines/phthalimide and formaldehyde anticipating effective as antimicrobial agents.

Methods: The efficient syntheses of substituted thiadiazole were done simply by reaction of substituted benzoic acid with thiosemicarbazide in presence of only conc. sulphuric acid. The isolated products were further subjected for Mannich reaction and evaluated for antibacterial activity.

Results: Three substituted thiadiazoles (BA-1 to BA-3) were synthesized by solvent less efficient synthesis and their Mannich base derivates were also prepared with phthalimide, p-nitro/methyl/chloro-aniline. All characterized products were screened for antibacterial and antifungal activities. Among these compounds having nitro group (3,7,13) showed maximum activity followed by phthalimide, chloro and methyl groups.

Conclusion: Thiadiazole-Mannich bases derivatives exhibited better antimicrobial activities then their starting components (BA-1 to BA-3) indicated joining different pharmacophore in the same molecule have increased activity.

 

Keywords: Thiadiazole Mannich bases derivatives, Characterization, Antimicrobial activities

Downloads

Download data is not yet available.

References

1. Küçükgüzel G, Kocatepe A, Clercq ED, Şahin F, Güllüce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem 2006;41:353–9.
2. Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumar NS. Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. Eur J Med Chem 2008;43:261–7.
3. Basavaraja KM, Somasekhar B, Appalaraju S. Synthesis and biological activity of some 2-[3-substituted-2-thione-1,3,4-thiazole-5-yl]aminobenzothiazoles. Indian J Heterocycl Chem 2008;18:69–72.
4. AgarwalT, Gupta P, Asthana S, Khursheed A. In silico analysis to access the antibacterial effect of thiazides on pdfs: molecular docking approach. Int J Pharm Pharm Sci 2014;6:387-91.
5. Verma A, Saraf SK. 4-Thiazolidinone–Abiologically actives caffold. Eur J Med Chem 2008;43:897–905.
6. Jiang B, Gu X. H Syntheses and cytotoxicity evaluation of bis (indolyl) thiazole, bis (indolyl) pyrazinone and bis (indolyl) pyrazine: analogues of cytxic marine bis (indole) alkaloid. Bioorg Med Chem 2000:8:363–71.
7. Pawar S, Sawant S, Nerkar A, Bhosale A. In silico design, synthesis and pharmacological screening of novel 2-(6-substituted benzo [d] thiazol-2-yl) isoindoline-1, 3-diones as potential cox-2 inhibitors for anti-inflammatory activity. Int J Pharm Pharm Sci 2014;6:353-7.
8. Ravichandran V, Mohan S, Kumar KS. Synthesis and antimicrobial activity of Mannich bases of isatin and its derivatives with 2-[(2,6-dichlorophenyl)amino]phenylacetic acid (07-2496LP). ARKIVOC J 2007;14:51-7.
9. Syamala M. Recent progress in three-component reactions. Organic Preparations and Procedures International: Journal Organic Synthesis 2009;41:1–68.
10. Bala S, Sharma N, Kajal A, Kamboj S, Saini V. Mannich bases: an important pharmacophore in present scenario. Int J Med Chem 2014. Available from: URL: http://dx.doi.org/10.1155/ 2014/191072. [Last accessed on 10 Jun 2015]
11. Subramaniapillai SG. Mannich reaction: A versatile and convenient approach to bioactive Skeletons. J Chem Sci 2013;125 : 467–82.
12. Meenakshi K, Gopal N, Sarangapani M. Synthesis, characterization and antimicrobial activity of some novel Schiff and mannich bases of isatin. Int J Pharm Pharm Sci 2014;6:318-22.
13. Pandey VK, Negi HS, Joshi MN, Bajpai SK. Synthesis and biological activity of some new benzophenothiazines. Indian J Chem 2003;42B:206–10.
14. Rahman A, Choudhary MI, Thomsen WJ. Bioassay techniques for drug development. Harwood Academic Publishers, The Netherlands; 2001. p. 16
15. Jha A, Murthy YLN, Sanyal U, Durga G. Rapid synthesis, characterization, anticancer and antimicrobial activity studies of substituted thiadiazoles and their di nucleating ligand metal complexes. Med Chem Res 2012;21:2548-56.
16. Ghatolea AM, Lanjewarb KR, Gaidhane MK. Synthesis and anti-microbial activity of some substituted bis[2-((e)-2-(4-benzylideneamino)thiazol-4-yl)-4-methylphenol] metal complexes. Int J Pharm Pharm Sci 2014;6:142-6.
17. Vishnuvardhanaraj G, Tamilvendan D, Amaladasan M. Synthesis, characterization and biological activities of cinnamaldehyde’s Mannich bases. Int J Pharm Pharm Sci 2013;5:821-5.
18. Bamnela R, Shrivastava SP. Synthesis and evaluation of some N-Mannich base of isoindol-1,3(2H-dione) derivatives as potential antimicrobial, anthelmintic and in secticidal agents. Indian J Chem 2014;53B:1128-35.
19. Sahin D, Bayrak H, Demirbas A, Demirbas N, Karaoglu SA. Design and synthesis of new 1, 2, 4-triazole derivatives containing morpholine moiety as antimicrobial agents. Turk J Chem 2012;36:411–26.
20. Kanchana SN, Burra V, Nath KR. Novel synthesis and anti-microbial activity study of innovative mannich bases containing 2-phenoxy-1,3,2-dioxa phospholanes and indole systems. Orient J Chem 2014;30:1349-60.
21. Al-Azzawi AM, Al-Razzak MSA. Synthesis, characterization and antibacterial screening of new Schiff bases linked to phthalimide. Int J Res Pharm Chem 2013;3:682-90.
22. Desai NC, Pandya DD, Kotadiya GM, Desai P. Synthesis and characterization of novel benzimidazole bearing pyrazoline derivatives as potential antimicrobial agents. Med Chem Res 2014;23:1474-87.
23. Moger M, Satam V, Govindaraju DRC, Paniraj AS, Gopinath VS, Hindupur RM, et al. Synthesis and antimicrobial properties of 1,3,4-oxadiazole analogs containing dibenzosuberane moiety. J Braz Chem Soc 2014;25:104-11.
24. De P, Baltas M, Bedos-Belval F. Cinnamic acid derivatives as anticancer agents-a review. Curr Med Chem 2011;18:1672-703.
Statistics
689 Views | 1375 Downloads
How to Cite
Balaji, K., P. Bhatt, D. Mallika, and A. Jha. “DESIGN, SYNTHESIS AND ANTIMICROBIAL EVALUATION OF SOME MANNICH BASE DERIVATIVE OF 2-(SUBTITUTED)-5-AMINO-THIADIAZOLES”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 7, no. 11, Aug. 2015, pp. 145-9, https://innovareacademics.in/journals/index.php/ijpps/article/view/7961.
Section
Original Article(s)