In an attempt to find a new class of antimicrobial agents, a series of indolothiazolidinone, oxazolidinone, and azetidene analogs of benzenesulfonyl chloride have been synthesized and evaluated for their antibacterial activity against S. aureus, S. typhi and E. coli, expressed as the minimum inhibitory concentration (MIC50,μg/mL). Some of the synthesized compounds (4a–4d, 5a– 5d, and 6a–6d) exhibit promising antibacterial activity that is attributed to their spiro structure.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
U. Misra, A. Hitkari, A. K. Saxena, et al., Eur. J. Med. Chem., 31, 629 (1996).
P. K. Dubey, T. Venkateshwar Kumar, P. Reddanna, and K. Anil Kumar, Indian J. Chem., 45B, 2128 (2006).
R. Sharma, Chem. Abstr., 136, 134670d (2002).
V. N. Sonar, Y. Shaik Khadar, and N. Sreenivasulu, Ind. J. Heterocycl. Chem., 19, 299 (2001).
E. Bansal, V. K. Srivastava, and A. Kumar, Indian J. Chem., 39B, 357 (2000).
M. Amir, N. Dhar, and S. K. Tiwari, Indian J. Chem., 36B,96 (1997).
A. P. Rani, K. Bajaj, V. K. Srivastava, et al., Arzneim Forsch. Drug Res., 55, 31 (2003).
P. Sharma, A. Kumar, and P. Pandey, Indian J. Chem., 45B, 2077 (2006).
S. J. Biradar and Y. S. Manjunath, Indian J. Chem., 43B, 389 (2004).
T. R. Pardasani, P. Pardasani, D. Sherry, and V. Chaturvedi, Indian J. Chem., 40B, 1275 (2001).
S. G. Gadaginamath, S. A. Shyadligeri, and R. R. Kavali, Indian J. Chem., 37B, 1137 (1998).
J. Mohan and V. Kumar, Indian J. Chem., 36B, 1030 (1997).
(a) R. M. Williams and R. J. Cox, Acc. Chem. Res., 36, 127 (2003); (b) C. V. Galliford and K. A. Scheidt, Angew. Chem. Int. Ed., 46, 8748 (2007); (c) C. B. Cui, H. Kakeya, and H. Osada, J. Antibiot., 49, 832 (1996); (d) C. B. Cui, H. Kakeya, and H. Osada, Tetrahedron, 52, 12651 (1996); (e) C. B. Cui, H. Kakeya, and H. Osada, Tetrahedron, 53, 59 (1997); (f) C. B. Cui, H. Kakeya, G. Okada, et al., J. Antibiot., 48, 1382 (1995); (g) C. B. Cui, H. Kakeya, G. Okada, et al., J. Antibiot., 49, 527 (1996); (h) T.-H. Kang, K. Matsumoto, Y. Murakami, et al., Eur. J. Pharmacol., 444, 39 (2002).
(a) C. Fischer, C. Meyers, and E. M. Carreira, Helv. Chim. Acta, 83, 1175 (2000); (b) P. B. Alper, C. Meyers, A. Lerchner, et al., Angew. Chem. Int. Ed., 38, 3186 (1999); (c) A. Ashimori, B. Bachand, L. E. Overmann, and D. J. Poon, J. Am. Chem. Soc., 120, 6477 (1998); (d) T. Matsuura, L. E. Overmann, and D. J. Poon, J. Am. Chem. Soc., 120, 6500 (1998).
L. Jaish and S. K. Srivastava, Chem. Abstr., 136, 805 (2002).
K. S. Srivastava, L. S. Srivastava, and D. S. Srivastava, Indian J. Chem., 39B, 464 (2000).
V. Lather and R. V. P. Chowdary, Indian J. Pharm Sci., 65, 576 (2003).
M. K. Thaker, V. V. Kacchadia, and S. H. Joshi, Indian J. Chem., 42B, 1544 (2003).
N. B. Patel and S. D. Patel, Pharm. Chem. J., 43, 305 (2009).
Clinical and Laboratory Standard Institute (Formerly NCCLS), Methods for Determining Bactericidal Activity of Antimicrobial Agents: Approved Guidelines (Approved Standard M26-A) [ISBN 1-56238-384-1] (NCCLS, Wayne, Pennsylvania, USA, 1999).
Acknowledgements
The authors are grateful to University Grant Commission, New Delhi, and to the University of Mumbai for financial support. We greatly appreciate the supportive environment encouraged at C. K. Thakur College and thanks to Dr. S. T. Gadade, Principal, C. K. Thakur College, for providing laboratory and other facilities.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Deokar, H., Chaskar, J. & Chaskar, A. Synthesis, screening and antimicrobial activity evaluation of spiro indolothiazolidinone, oxazolidinone and azetidene derivatives of benzenesulfonyl chloride. Pharm Chem J 46, 429–434 (2012). https://doi.org/10.1007/s11094-012-0814-0
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-012-0814-0