Copyright (c) 2023 Tirth Thaker, Sweta Maurya, Dipen Panchani
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Antimicrobial Screening and ADME Investigations of Novel Bi-Heterocycles containing Benzopyrones with Pyrazolone
Corresponding Author(s) : Tirth Thaker
Asian Journal of Chemistry,
Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024
Abstract
Few 3-methyl-1-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetyl-4,5-dihydro-1H-pyrazol-5-one derivatives were synthesized and their structures were characterized by FTIR, 1H NMR and mass spectrometry. To assess the potential antibacterial action of a conventional medicine, a biological screening was done on Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Pseudomonas aeruginosa. Furthermore, these medicines underwent in silico ADME evaluation. Although all compounds successfully underwent the ADME evaluation, only a limited number of compounds passed the projected toxicity test.
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- D.R. Vianna, G. Bubols, G. Meirelles, B.V. Silva, M. Lanznaster, A. da Rocha, J.M. Monserrat, S.C. Garcia, G. von Poser and V.L. Eifler-Lima, Int. J. Mol. Sci., 13, 7260 (2012); https://doi.org/10.3390/ijms13067260
- C. Elisabeth, A. Bettina, M.G. Roy, C. Francisco, E. Thomas, L. Stephane, P. Bruno and P. Michelle, Eur. J. Med. Chem., 41, 1470 (2006); https://doi.org/10.1016/j.ejmech.2006.06.012
- F.A.-F. Ragab, N.M. Abdel-Gawad, H.H. Georgey and M.F. Said, Chem. Pharm. Bull., 61, 834 (2013); https://doi.org/10.1248/cpb.c13-00314
- R.W. Bürli, H. Xu, X. Zou, K. Muller, J. Golden, M. Frohn, M. Adlam, M.H. Plant, M. Wong, M. McElvain, K. Regal, V.N. Viswanadhan, P. Tagari and R. Hungate, Bioorg. Med. Chem Lett., 16, 3713 (2006); https://doi.org/10.1016/j.bmcl.2006.04.068
- S.A.M. El-Hawash, El-Sayed A.M. Badawey and I.M. El-Ashmawey, J. Med. Chem., 41, 155 (2006); https://doi.org/10.1016/j.ejmech.2005.09.006
- N. Hidehiko, O. Ryo, K. Ayako, S. Takayoshi and M. Naoki, Bioorg. Med. Chem. Lett., 16, 5939 (2006); https://doi.org/10.1016/j.bmcl.2006.09.005
- R. Ramajayam, K.-P. Tan, H.-G. Liu and P.-H. Liang, Bioorg. Med. Chem., 18, 7849 (2010); https://doi.org/10.1016/j.bmc.2010.09.050
- M.J. Ahsan, J.G. Samy, C.B. Jain, K.R. Dutt, H. Khalilullah and M.S. Nomani, Bioorg. Med. Chem. Lett., 22, 969 (2012); https://doi.org/10.1016/j.bmcl.2011.12.014
- F. Moreau, N. Desroy, J.M. Genevard, V. Vongsouthi, V. Gerusz, G. Le Fralliec, C. Oliveira, S. Floquet, A. Denis, S. Escaich, M. Busemann, K. Wolf and A. Aschenbrenner, Bioorg. Med. Chem. Lett., 18, 4022 (2008); https://doi.org/10.1016/j.bmcl.2008.05.117
- S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr and H.M.A. Ashour, Bioorg. Med. Chem., 17, 882 (2009); https://doi.org/10.1016/j.bmc.2008.11.035
- K.K. Sivakumar and A. Rajasekaran, J. Pharm. Bioallied Sci., 5, 126 (2013); https://doi.org/10.4103/0975-7406.111828
- K.K. Sivakumar, A. Rajasekharan, R. Rao and B. Narasimhan, Indian J. Pharm. Sci., 75, 463 (2013); https://doi.org/10.4103/0250474X.119832
- S.V. Bhandari, S.C. Dangre, K.G. Bothara, A.A. Patil, A.P. Sarkate, D.K. Lokwani, S.T. Gore, B.J. Deshmane, V.T. Raparti and C.V. Khachane, Eur. J. Med. Chem., 44, 4622 (2009); https://doi.org/10.1016/j.ejmech.2009.06.035
- T. Watanabe and M. Egawa, J. Pharmacol. Exp. Ther., 268, 1597 (1994); https://doi.org/10.1016/S0021-5198(19)51716-4
- H. Kawai, H. Nakai, M. Suga, S. Yuki, T. Watanabe and K.I. Saito, J. Pharmacol. Exp. Ther., 281, 921 (1997).
- A. Kimata, H. Nakagawa, R. Ohyama, T. Fukuuchi, S. Ohta, T. Suzuki and N. Miyata, J. Med. Chem., 50, 5053 (2007); https://doi.org/10.1021/jm070688r
- Y. Higashi, D. Jitsuiki, K. Chayama and M. Yoshizumi, Recent Adv. Cardiovasc. Drug Discov., 1, 85 (2006); https://doi.org/10.2174/157489006775244191
- A. Schonberg and N. Latif, J. Am. Chem. Soc., 76, 6208 (1954); https://doi.org/10.1021/ja01652a112
- A.K. Mitra, S.K. Misra and A. Patra, Synth. Commun., 10, 915 (1980); https://doi.org/10.1080/00397918008061851
- L.A. Singer and N.P. Kong, J. Am. Chem. Soc., 88, 5213 (1966); https://doi.org/10.1021/ja00974a033
- M. Loncaric, D. Gaso-Sokac, S. Jokic and M. Molnar, Biomolecules, 10, 151 (2020); https://doi.org/10.3390/biom10010151
- M.S.Y. Khan and M. Akhtar, Indian J. Chem., 42B, 900 (2003).
- A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45(4_ts), 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
- A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
- A. Daina and V. Zoete, ChemMedChem, 11, 1117 (2016); https://doi.org/10.1002/cmdc.201600182
References
D.R. Vianna, G. Bubols, G. Meirelles, B.V. Silva, M. Lanznaster, A. da Rocha, J.M. Monserrat, S.C. Garcia, G. von Poser and V.L. Eifler-Lima, Int. J. Mol. Sci., 13, 7260 (2012); https://doi.org/10.3390/ijms13067260
C. Elisabeth, A. Bettina, M.G. Roy, C. Francisco, E. Thomas, L. Stephane, P. Bruno and P. Michelle, Eur. J. Med. Chem., 41, 1470 (2006); https://doi.org/10.1016/j.ejmech.2006.06.012
F.A.-F. Ragab, N.M. Abdel-Gawad, H.H. Georgey and M.F. Said, Chem. Pharm. Bull., 61, 834 (2013); https://doi.org/10.1248/cpb.c13-00314
R.W. Bürli, H. Xu, X. Zou, K. Muller, J. Golden, M. Frohn, M. Adlam, M.H. Plant, M. Wong, M. McElvain, K. Regal, V.N. Viswanadhan, P. Tagari and R. Hungate, Bioorg. Med. Chem Lett., 16, 3713 (2006); https://doi.org/10.1016/j.bmcl.2006.04.068
S.A.M. El-Hawash, El-Sayed A.M. Badawey and I.M. El-Ashmawey, J. Med. Chem., 41, 155 (2006); https://doi.org/10.1016/j.ejmech.2005.09.006
N. Hidehiko, O. Ryo, K. Ayako, S. Takayoshi and M. Naoki, Bioorg. Med. Chem. Lett., 16, 5939 (2006); https://doi.org/10.1016/j.bmcl.2006.09.005
R. Ramajayam, K.-P. Tan, H.-G. Liu and P.-H. Liang, Bioorg. Med. Chem., 18, 7849 (2010); https://doi.org/10.1016/j.bmc.2010.09.050
M.J. Ahsan, J.G. Samy, C.B. Jain, K.R. Dutt, H. Khalilullah and M.S. Nomani, Bioorg. Med. Chem. Lett., 22, 969 (2012); https://doi.org/10.1016/j.bmcl.2011.12.014
F. Moreau, N. Desroy, J.M. Genevard, V. Vongsouthi, V. Gerusz, G. Le Fralliec, C. Oliveira, S. Floquet, A. Denis, S. Escaich, M. Busemann, K. Wolf and A. Aschenbrenner, Bioorg. Med. Chem. Lett., 18, 4022 (2008); https://doi.org/10.1016/j.bmcl.2008.05.117
S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr and H.M.A. Ashour, Bioorg. Med. Chem., 17, 882 (2009); https://doi.org/10.1016/j.bmc.2008.11.035
K.K. Sivakumar and A. Rajasekaran, J. Pharm. Bioallied Sci., 5, 126 (2013); https://doi.org/10.4103/0975-7406.111828
K.K. Sivakumar, A. Rajasekharan, R. Rao and B. Narasimhan, Indian J. Pharm. Sci., 75, 463 (2013); https://doi.org/10.4103/0250474X.119832
S.V. Bhandari, S.C. Dangre, K.G. Bothara, A.A. Patil, A.P. Sarkate, D.K. Lokwani, S.T. Gore, B.J. Deshmane, V.T. Raparti and C.V. Khachane, Eur. J. Med. Chem., 44, 4622 (2009); https://doi.org/10.1016/j.ejmech.2009.06.035
T. Watanabe and M. Egawa, J. Pharmacol. Exp. Ther., 268, 1597 (1994); https://doi.org/10.1016/S0021-5198(19)51716-4
H. Kawai, H. Nakai, M. Suga, S. Yuki, T. Watanabe and K.I. Saito, J. Pharmacol. Exp. Ther., 281, 921 (1997).
A. Kimata, H. Nakagawa, R. Ohyama, T. Fukuuchi, S. Ohta, T. Suzuki and N. Miyata, J. Med. Chem., 50, 5053 (2007); https://doi.org/10.1021/jm070688r
Y. Higashi, D. Jitsuiki, K. Chayama and M. Yoshizumi, Recent Adv. Cardiovasc. Drug Discov., 1, 85 (2006); https://doi.org/10.2174/157489006775244191
A. Schonberg and N. Latif, J. Am. Chem. Soc., 76, 6208 (1954); https://doi.org/10.1021/ja01652a112
A.K. Mitra, S.K. Misra and A. Patra, Synth. Commun., 10, 915 (1980); https://doi.org/10.1080/00397918008061851
L.A. Singer and N.P. Kong, J. Am. Chem. Soc., 88, 5213 (1966); https://doi.org/10.1021/ja00974a033
M. Loncaric, D. Gaso-Sokac, S. Jokic and M. Molnar, Biomolecules, 10, 151 (2020); https://doi.org/10.3390/biom10010151
M.S.Y. Khan and M. Akhtar, Indian J. Chem., 42B, 900 (2003).
A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45(4_ts), 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
A. Daina and V. Zoete, ChemMedChem, 11, 1117 (2016); https://doi.org/10.1002/cmdc.201600182