SYNTHESIS, CHARACTERIZATION AND IN VITRO ANTIMICROBIAL EVALUATION OF SOME NEW AMIDES OF THIOMORPHOLINE CARBOXYLATE

Authors

  • Vasudeva Reddy Nagavelli Department of Chemistry, Kakatiya University, Warangal 506009 India.
  • Kumaraswamy B Department of Chemistry, Kakatiya University, Warangal 506009 India.
  • Ranjith Kumar T Department of Chemistry, Kakatiya University, Warangal 506009 India.
  • Narsimha S Department of Chemistry, Kakatiya University, Warangal 506009 India.

Keywords:

Antimicrobial activity, Thiomorpholine, Trimethylaluminum, LiHMDS

Abstract

Objective: Synthesis and antimicrobial evaluation of some new amides of Thiomorpholine caboxylate.

Methods: A series of new amides of Thiomorpholine caboxylate were synthesized by reacting 4-tert-butyl 2-methyl thiomorpholine-2,4-dicarboxylate 1,1-dioxide with primary amines in presence of Trimethyl aluminum in toluene at ambient temperature in good yields. 4-tert-butyl 2-methyl thiomorpholine-2,4-dicarboxylate 1,1-dioxide was synthesized by reacting tert-butyl thiomorpholine-4-carboxylate 1,1-dioxide with methyl chloroformate in presence of LiHMDS (1M in THF) at -78oC for the first time. The newly synthesized compounds were characterized by IR, 1HNMR, 13C NMR, Mass spectral studies and elemental analysis.

Results: A series of new amides of Thiomorpholine carboxylate were synthesized in good yields and all the compounds were screened for their In-vitro antimicrobial activities.

Conclusion: Preliminary results revealed that the synthesized compounds were showed moderate to good antibacterial and antifungal activity.

Downloads

Download data is not yet available.

Author Biography

Vasudeva Reddy Nagavelli, Department of Chemistry, Kakatiya University, Warangal 506009 India.

Chemistry

References

Bei Han, Jing Long Liu, Yi Huan, Peng Li, Qi Wu and Zi Yun Lin et al. Design, synthesis and primary activity of thiomorpholine derivatives as DPP-IV inhibitors. Chin Chem Lett 2012;23(3):297-300.

N. Ziakas, Eleni A. Rekka, Antonios M. Gavalas, Phaedra T. Eleftheriou, Panos N. Kourounaki New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. Bioorg Med Chem 2006;14(16):5616-24.

Michael C, Chrysselis, Eleni A, Rekka and Panos N.Kourounakis. Hypocholesterolemic and Hypolipidemic activity of some novel Morpholine derivatives with Antioxidant Activity. J Med Chem 2000;43 (4): 609–12.

Michael C, Chrysselis, Eleni A, Rekka, Ioanna C. Siskou, and Panos N. Kourakounakis. Nitric Oxide releasing Morpholine derivatives as Hypolipidemic and Antioxidant Agents. J Med Chem 2002; 45 (24): 5406–09.

Shanshan Yan, Marvin J. Miller, Timothy A, Wencewicz and Ute Mollmann. Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry. Bioorg Med Chem Letts 2010;20(3):1302-05.

Carolina de Mattos Duarte,b, Hugo Verlia, Joao Xavier de Araujo-Junior, Isac Almeida de Medeiros, Eliezer J. Barreiro, Carlos Alberto Manssour Fraga. New optimized piperamide analogues with potent in vivo hypotensive properties. Eur J Pharm Sci 2004;23 (4-5) :363–69.

D. Jonathan Bennett,* Alison Anderson, Kirsteen Buchanan, Alan Byford, Andrew Cooke, David K. Gemmell, Niall M.et al. Novel water soluble 2,6-dimethoxyphenyl ester derivatives with intravenous anaesthetic activity.Bioorg Med Chem Letts 2003;13(12) 1971–75.

Joel Morris, Donn G. Wishka, William R. Humphrey, Alice H. Lin, Ann L. Wiltse, Christopher W. Benjamin et al. Synthesis and biological activity of a potent antiplatelet 7-aminofurochromone. Bioorg Med Chem Letts 1994; 4(21): 2621-26.

Senthikumar P, Dinakaran M, Yogeeswari P, Sriram D, China A, Nagaraja V.Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids. E J Med Chem 2009;44(1):345-58.

Sanjay K. Srivastava, Aji Abraham, Beena Bhat, Manu Jaggi, Anu T. Singh, Vinod K. Sanna et al. Synthesis of 13-amino costunolide derivatives as anticancer agents. Bioorg Med Chem Letts 2006;16 (16) :4195 – 99.

Maria Leticia de Castro Barbosa , Gabriela Muniz de Albuquerque Melo, Yolanda Karla Cupertino da Silva , Raquel de Oliveira Lopes, Everton Teno rio de Souza , Aline Cavalcanti de Queiroz c et al. Synthesis and pharmacological evaluation of N-phenyl-acetamide sulfonamides designed as novel non-hepatotoxic analgesic candidates. Eur J Med Chem 2009; 44 (9):3612–20.

Mariangela Biava, Giulio C. Porretta, Giovanna Poce, Alessandro De Logu, Rita Meleddu, Edda De Rossi et.al. 1,5-Diaryl-2-ethyl pyrrole derivatives as antimycobacterial agents: Design, synthesis, and microbiological evaluation. Eur J Med Chem 2009; 44 (11):4734 – 38.

Kunio Saruta, Tsuyoshi Ogiku. A traceless solid phase synthesis of Thiomorpholin-3-ones. Tetrahedron Lett 2008;49(3):424-27.

Stefano Marcaccini, Roberto Pepino, Tomas Torroba, Daniel Miguel and Maria Garcia-Valverde. Synthesis of thiomorpholines by an intramolecular Ugi reaction. Tetrahedron Lett 2002;43(47):8591-93.

Benderly A, Stavchansky S. A new synthesis of carboxylic acid hydrazides via organo aluminum reagents. Tetrahedron Lett 1988;29(7):739-40.

Published

01-09-2014

How to Cite

Nagavelli, V. R., K. B, R. K. T, and N. S. “SYNTHESIS, CHARACTERIZATION AND IN VITRO ANTIMICROBIAL EVALUATION OF SOME NEW AMIDES OF THIOMORPHOLINE CARBOXYLATE”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 9, Sept. 2014, pp. 418-21, https://journals.innovareacademics.in/index.php/ijpps/article/view/2506.

Issue

Section

Original Article(s)