Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Novel Oxazolidinone Derivatives Bearing Benzo[b]thiophene Moiety and their Antimicrobial Evaluation
Corresponding Author(s) : Vijay J. Medhane
Asian Journal of Chemistry,
Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022
Abstract
Literature survey revealed that the oxazolidinone derivatives exhibit pharmacological significance. Thus, by targeting to design new antimicrobial agent, a novel series of oxazolidinone derivatives (11a-t) having benzo[b]thiophene moiety were synthesized. Chemical structures of the synthesized compounds were confirmed through spectroscopic techniques such as IR, NMR and Mass spectroscopy. All the new synthesized compounds were subjected to in vitro antimicrobial testing by estimating zone of inhibition toward Gram-positive pathogens like Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 25923 and Streptococcus pyogens ATCC 8668.
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- A.K. Barker, K. Brown, M. Ahsan, S. Sengupta and N. Safdar, BMC Public Health, 17, 333 (2017); https://doi.org/10.1186/s12889-017-4261-4
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- Y. Li and W. Xu, Biosci. Rep., 38, BSR20171125 (2018); https://doi.org/10.1042/BSR20171125
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- M.S. Malamas, J. Sredy, C. Moxham, A. Katz, W. Xu, R. McDevitt, F.O. Adebayo, D.R. Sawicki, L. Seestaller, D. Sullivan and J.R. Taylor, J. Med. Chem., 43, 1293 (2000); https://doi.org/10.1021/jm990560c
- D.A. Kennedy and L.A. Summers, Heterocycl. Chem., 18, 409 (1981); https://doi.org/10.1002/jhet.5570180236
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- P. Lu, M.L. Schrag, D.E. Slaughter, C.E. Raab, M. Shou and A.D. Rodrigues, Drug Metab. Dispos., 31, 1352 (2003); https://doi.org/10.1124/dmd.31.11.1352
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References
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K.P. Rakesh, M.H. Marichannegowda, S. Srivastava, X. Chen, S. Long, C.S. Karthik, P. Mallu and H.L. Qin, ACS Comb. Sci., 20, 681 (2018); https://doi.org/10.1021/acscombsci.8b00088
M.K. Byrne, S. Miellet, A. McGlinn, J. Fish, S. Meedya, N. Reynolds and A.M. van Oijen, BMC Public Health, 19, 1425 (2019); https://doi.org/10.1186/s12889-019-7796-8
G.-F. Zha, J. Leng, N. Darshini, T. Shubhavathi, H.K. Vivek, A.M. Asiri, H.M. Marwani, K.P. Rakesh, N. Mallesha and H.-L. Qin, Bioorg. Med. Chem. Lett., 27, 3148 (2017); https://doi.org/10.1016/j.bmcl.2017.05.032
K. Lewis, Nat. Rev. Drug Discov., 12, 371 (2013); https://doi.org/10.1038/nrd3975
V.M. D’Costa, C.E. King, L. Kalan, M. Morar, W.L. Sung, C. Schwarz, D. Froese, G. Zazula, F. Calmels, R. Debruyne, G.B. Golding, H.N. Poinar and G.D. Wright, Nature, 477, 457 (2011); https://doi.org/10.1038/nature10388
N. Pandit, R.K. Singla and B. Shrivastava, Int. J. Med. Chem., 2012, 1 (2012); https://doi.org/10.1155/2012/159285
J.V.N.V. Prasad, Curr. Opin. Microbiol., 10, 454 (2007); https://doi.org/10.1016/j.mib.2007.08.001
L.M. Deshpande, M. Castanheira, R.K. Flamm and R.E. Mendes, J. Antimicrob. Chemother., 73, 2314 (2018); https://doi.org/10.1093/jac/dky188
R.K. Flamm, D.J. Farrell, H.S. Sader and R.N. Jones, J. Antimicrob. Chemother., 69, 1589 (2014); https://doi.org/10.1093/jac/dku025
M.A. Pfaller, R.K. Flamm, R.N. Jones, D.J. Farrell and R.E. Mendes, J. Antimicrob. Chemother., 60, 5393 (2016); https://doi.org/10.1128/AAC.00881-16
C. Roger, J.A. Roberts and L. Muller, Clin. Pharmacokinet., 57, 559 (2018); https://doi.org/10.1007/s40262-017-0601-x
S.M.R. Hashemian, T. Farhadi and M. Ganjparvar, Drug Des. Devel. Ther., 12, 1759 (2018); https://doi.org/10.2147/DDDT.S164515
Y. Li and W. Xu, Biosci. Rep., 38, BSR20171125 (2018); https://doi.org/10.1042/BSR20171125
L. Maarouf, H. Omar, M. El-Nakeeb and A. Abouelfetouh, Eur. J. Clin. Microbiol. Infect. Dis., 40, 815 (2021); https://doi.org/10.1007/s10096-020-04045-w
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M.J. Pucci and K. Bush, Clin. Microbiol. Rev., 26, 792 (2013); https://doi.org/10.1128/CMR.00033-13
C.W. Ford, G.E. Zurenko and M.R. Barbachyn, Curr. Drug Targets Infect. Disord., 1, 181 (2001); https://doi.org/10.2174/1568005014606099
L.L. Silver, Clin. Microbiol. Rev., 24, 71 (2011); https://doi.org/10.1128/CMR.00030-10
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H.U. Bryant and W.H. Dere, Proc. Soc. Exp. Biol. Med., 217, 45 (1998); https://doi.org/10.3181/00379727-217-44204
Z. Qin, I. Kastrati, R.E.P. Chandrasena, H. Liu, P. Yao, P.A. Petukhov, J.L. Bolton and G.R.J. Thatcher, J. Med. Chem., 50, 2682 (2007); https://doi.org/10.1021/jm070079j
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G. Naganagowda and B. Padmashali, Phosphorus Sulfur Silicon Rel. Elem., 185, 1691 (2010); https://doi.org/10.1080/10426500903241713
M.S. Malamas, J. Sredy, C. Moxham, A. Katz, W. Xu, R. McDevitt, F.O. Adebayo, D.R. Sawicki, L. Seestaller, D. Sullivan and J.R. Taylor, J. Med. Chem., 43, 1293 (2000); https://doi.org/10.1021/jm990560c
D.A. Kennedy and L.A. Summers, Heterocycl. Chem., 18, 409 (1981); https://doi.org/10.1002/jhet.5570180236
C.D. Jones, M.G. Jevnikar, A.J. Pike, M.K. Peters, L.J. Black, A.R. Thompson, J.F. Falcone and J.A. Clemens, J. Med. Chem., 27, 1057 (1984); https://doi.org/10.1021/jm00374a021
V.C. Jordan, J. Med. Chem., 46, 883 (2003); https://doi.org/10.1021/jm020449y
V.C. Jordan, J. Med. Chem., 46, 1081 (2003); https://doi.org/10.1021/jm020450x
P. Lu, M.L. Schrag, D.E. Slaughter, C.E. Raab, M. Shou and A.D. Rodrigues, Drug Metab. Dispos., 31, 1352 (2003); https://doi.org/10.1124/dmd.31.11.1352
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D.N. Wilson, Nat. Rev. Microbiol., 12, 35 (2014); https://doi.org/10.1038/nrmicro3155
G.R. Jadhav, D.G. Deshmukh, V.J. Medhane, V.B. Gaikwad and A.D. Bholay, Heterocycl. Commun., 22, 123 (2016); https://doi.org/10.1515/hc-2015-0215