Copyright (c) 2019 AJC
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Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives
Corresponding Author(s) : Mohamad Yusuf
Asian Journal of Chemistry,
Vol. 31 No. 1 (2019): Vol 31 Issue 1
Abstract
In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR, 1H NMR, 13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.
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N.A. Bokach, M.L. Kuznetsov and V.Y. Kukushkin, Coord. Chem. Rev., 255, 2946 (2011); https://doi.org/10.1016/j.ccr.2011.07.001.
M. Al-Ghorbani, U. Al-Timari and T.F.S.A. Khanum, Res. J. Chem. Sci., 4, 60 (2014).
J. Kaur, B. Singh and K.K. Singal, Indian J. Chem., 44B, 1476 (2005).
Y. Xing and N.X. Wang, Coord. Chem. Rev., 256, 938 (2012); https://doi.org/10.1016/j.ccr.2012.01.002.
S. Shah, R. Badru and B. Singh, Synth. Commun., 43, 1073 (2013); https://doi.org/10.1080/00397911.2011.622063.
F.A. Almashal, J. Basrah. Res. Sci., 37, 128 (2011).
R.D. Hinton and E.G. Janzen, J. Org. Chem., 57, 2646 (1992); https://doi.org/10.1021/jo00035a020.
M. Thirumalaikumar, S. Sivasubramanian, A. Ponnuswamy and P. Mohan, Eur. J. Med. Chem., 31, 905 (1996); https://doi.org/10.1016/S0223-5234(97)89854-6.
G. Broggini, C. La Rosa, T. Pilati, A. Terraneo and G. Zecchi, Tetrahedron, 57, 8323 (2001); https://doi.org/10.1016/S0040-4020(01)00785-2.
A. Zeghdaoui, B. Tuccio, J.-P. Finet, V. Cerri and P. Tordo, J. Chem. Soc. Perkin Trans. II, 2087 (1995); https://doi.org/10.1039/P29950002087.
A. Kaur and B. Singh, J. Heterocycl. Chem., 51, 1421 (2014); https://doi.org/10.1002/jhet.1838.
A. Kaur, B. Singh and A.S. Jaggi, Bioorg. Med. Chem. Lett., 23, 797 (2013); https://doi.org/10.1016/j.bmcl.2012.11.080.
R. Badru, S. Shah and B. Singh, J. Heterocycl. Chem., 49, 336 (2012); https://doi.org/10.1002/jhet.794.
T.B. Nguyen, A. Martel, C. Gaulon, R. Dhal and G. Dujardin, Org. Prep. Proced. Int., 42, 387 (2010); https://doi.org/10.1080/00304948.2010.513886.
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A.O. Abdelhamid, A.H. El-Ghandour and A.A.M. El-Reedy, J. Chin. Chem. Soc., 55, 406 (2008); https://doi.org/10.1002/jccs.200800060.
B. Chakraborty, M.S. Chhetri, S. Kafley and A. Samanta, Indian J. Chem., 49B, 209 (2010).
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Basappa, M.P. Sadashiva, K. Mantelingu, S.N. Swamy and K.S. Rangappa, Bioorg. Med. Chem., 11, 4539 (2003); https://doi.org/10.1016/j.bmc.2003.08.007.
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H. Uno, M. Kurokawa, Y. Masuda and H. Nishimura, J. Med. Chem., 22, 180 (1979); https://doi.org/10.1021/jm00188a011.
A. Lilienkampf, M. Pieroni, B. Wan, Y. Wang, S.G. Franzblau and A.P. Kozikowski, J. Med. Chem., 53, 678 (2010); https://doi.org/10.1021/jm901273n.
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T. Ichiba, P.J. Scheuer and M. Kelly-Borges, J. Org. Chem., 58, 4149 (1993); https://doi.org/10.1021/jo00067a062.
R. Badru, P. Anand and B. Singh, Eur. J. Med. Chem., 48, 81 (2012); https://doi.org/10.1016/j.ejmech.2011.11.037.
P. Anand and B. Singh, Mini Rev. Med. Chem., 14, 623 (2014); https://doi.org/10.2174/1389557514999140728102737.
O. Bortolini, I. Mulani, A. De Nino, L. Maiuolo, M. Nardi, B. Russo and S. Avnet, Tetrahedron, 67, 5635 (2011); https://doi.org/10.1016/j.tet.2011.05.098.
S. Yavuz, H. Ozkan, N. Colak and Y. Yildirir, Molecules, 16, 6677 (2011); https://doi.org/10.3390/molecules16086677.
P. Roy and R.K. De, Indian J. Chem., 50B, 1513 (2011).
P. Anand and B. Singh, Bioorg. Med. Chem., 20, 521 (2012); https://doi.org/10.1016/j.bmc.2011.05.027.
N.P. Shetgiri and B.K. Nayak, Indian J. Chem., 44B, 1933 (2005).
P.K. Sarvesh and K. Nizamuddin, Arch. Pharm. Chem. Life Sci., 341, 418 (2008); https://doi.org/10.1002/ardp.200700197.
M. Yusuf and I. Solanki, J. Saudi Chem. Soc., 21, 251 (2017); https://doi.org/10.1016/j.jscs.2015.02.002.
M. Yusuf and M. Kaur, J. Heterocycl. Chem., 54, 735 (2017); https://doi.org/10.1002/jhet.2583.