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Design, Synthesis and Antimicrobial Evaluations of Novel 3,7-Disubstituted 2H-1-Benzopyran-2-ones
Corresponding Author(s) : Parmesh K. Dwivedi
Asian Journal of Chemistry,
Vol. 32 No. 9 (2020): Vol 32 Issue 9, 2020
Abstract
In present study, a novel class of 3,7-disubstituted 2H-1-benzopyran-2-one derivatives (3xa-3zc) bearing a basic ether side chain at C-7 and a substituted phenyl ring at C-3 of the coumarin ring is synthesized. These compounds have been evaluated for antimicrobial (antibacterial/antifungal) activities. Some of the compounds viz. 3xc, 3xe, 3xf, 3yb, 3yc and 3yf have shown significant antifungal activities against selective strains. Compounds 3xe, 3yb and 3yc with the MIC values of 1.56 μg/mL displayed better antifungal activity than fluconazole against Trichophyton mentagrophytes.
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- R.D.H. Murray, Nat. Prod. Rep., 12, 477 (1995); https://doi.org/10.1039/np9951200477
- A. Estévez-Braun and A.G. González, Nat. Prod. Rep., 14, 465 (1997); https://doi.org/10.1039/np9971400465
- R. Pratap and V. Ram, Chem. Rev., 114, 10476 (2014); https://doi.org/10.1021/cr500075s
- F. Borges, F. Roleira, N. Milhazes, L. Santana and E. Uriarte, Curr. Med. Chem., 12, 887 (2005); https://doi.org/10.2174/0929867053507315
- A. Lacy and R. O’Kennedy, Curr. Pharm. Des., 10, 3797 (2004); https://doi.org/10.2174/1381612043382693
- I. Kostova, Curr. Med. Chem. Anticancer Agents, 5, 29 (2005); https://doi.org/10.2174/1568011053352550
- J. Klenkar and M. Molnar, J. Chem. Pharm. Res., 7, 1223 (2015).
- E.A. Fayed, R. Sabour, M.F. Harras and A.B.M. Mehany, Med. Chem. Res., 28, 1284 (2019); https://doi.org/10.1007/s00044-019-02373-x
- C.A. Kontogiorgis and D.J. Hadjipavlou-Litina, J. Med. Chem., 48, 6400 (2005); https://doi.org/10.1021/jm0580149
- Y. Bansal, P. Sethi and G. Bansal, Med. Chem. Res., 22, 3049 (2013); https://doi.org/10.1007/s00044-012-0321-6
- K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas and D.N. Nicolaides, Curr. Pharm. Des., 10, 3813 (2004); https://doi.org/10.2174/1381612043382710
- T. Kawate, N. Iwase, M. Shimizu, S.A. Stanley, S. Wellington, E. Kazyanskaya and D.T. Hung, Bioorg. Med. Chem. Lett., 23, 6052 (2013); https://doi.org/10.1016/j.bmcl.2013.09.035
- B. Ramesh and K.V. Pugalendi, J. Med. Food, 9, 562 (2006); https://doi.org/10.1089/jmf.2006.9.562
- A.P. Dwivedi, S. Kumar, V. Varshney, A.B. Singh, A.K. Srivastava and D.P. Sahu, Bioorg. Med. Chem. Lett., 18, 2301 (2008); https://doi.org/10.1016/j.bmcl.2008.03.003
- M.J. Matos, D. Viña, P. Janeiro, F. Borges, L. Santana and E. Uriarte, Bioorg. Med. Chem. Lett., 20, 5157 (2010); https://doi.org/10.1016/j.bmcl.2010.07.013
- M.J. Matos, S. Vazquez-Rodriguez, E. Uriarte, L. Santana and D. Viña, Bioorg. Med. Chem. Lett., 21, 4224 (2011); https://doi.org/10.1016/j.bmcl.2011.05.074
- M.J. Matos, S. Vilar, R.M. Gonzalez-Franco, E. Uriarte, L. Santana, C. Friedman, N.P. Tatonetti, D. Viña and J.A. Fontenla, Eur. J. Med. Chem., 63, 151 (2013); https://doi.org/10.1016/j.ejmech.2013.02.009
- T. Ojala, S. Remes, P. Haansuu, H. Vuorela, R. Hiltunen, K. Haahtela and P. Vuorela, J. Ethnopharmacol., 73, 299 (2000); https://doi.org/10.1016/S0378-8741(00)00279-8
- M. Kawase, B. Varu, A. Shah, N. Motohashi, S. Tani, S. Debnath, S. Saito, S. Mahapatra, S.G. Dastidar and A.N. Chakrabarty, Arzneimittelforschung, 51, 67 (2001); https://doi.org/10.1055/s-0031-1300030
- P. Curir, F. Galeotti, M. Dolci, E. Barile and V. Lanzotti, J. Nat. Prod., 70, 1668 (2007); https://doi.org/10.1021/np070295v
- C. Montagner, S.M. de Souza, C. Groposo, F. Delle Monache, E.F.A. Smânia and A. Smânia Jr., Naturforsch., 63, 21 (2008); https://doi.org/10.1515/znc-2008-1-205
- T. Dandena and E. Milkyas, Adv. Pharmacol. Sci., 2019, 5419854 (2019); https://doi.org/10.1155/2019/5419854
- J. Sahoo and S.K. Paidesetty, J. Taibah Univ. Med. Sci., 12, 115 (2017); https://doi.org/10.1016/j.jtumed.2017.10.007
- M. Tegtmeier and W. Legrum, Arch. Pharm., 331, 143 (1998); https://doi.org/10.1002/(SICI)1521-4184(199804)331:4<143::AIDARDP143>3.0.CO;2-D
- V.M. Navarro-García, G. Rojas, M. Avilés, M. Fuentes and G. Zepeda, Mycoses, 54, e569 (2011); https://doi.org/10.1111/j.1439-0507.2010.01993.x
- M. Dakanali, E. Roussakis, A.R. Kay and H.E. Katerinopoulos, Tetrahedron Lett., 46, 4193 (2005); https://doi.org/10.1016/j.tetlet.2005.04.059
- D. Hadjipavlou-litina, C. Kontogiorgis, E. Pontiki, M. Dakanali, A. Akoumianaki and H.E. Katerinopoulos, J. Enzyme Inhib. Med. Chem., 22, 287 (2007); https://doi.org/10.1080/14756360601073914
- Z.M. Nofal, M.I. El-Zahar and S.S. Abd El-Karim, Molecules, 5, 99 (2000); https://doi.org/10.3390/50200099
- N. Batra, S. Batra, A. Prateek and B.N. Prakash, Int. J. Pharm., 3, 24 (2012).
- A.S. Negi, D. Chaturvedi, A. Gupta, S. Ray, A. Dwivedy and M.M. Singh, Bioorg. Med. Chem. Lett., 15, 99 (2005); https://doi.org/10.1016/j.bmcl.2004.10.031
- D. Chaturvedi, S. Ray, A.K. Srivastava and R. Chander, Bioorg. Med. Chem., 16, 2489 (2008); https://doi.org/10.1016/j.bmc.2007.11.062
- D. Chaturvedi, A.K. Chaturvedi, N. Mishra and V. Mishra, Org. Chem. Int., 10, 9148 (2012); https://doi.org/10.1039/C2OB26230D
- D. Chaturvedi, P.K. Dwivedi, A.K. Chaturvedi, N. Mishra, H.H. Siddiqui and V. Mishra, Med. Chem. Res., 24, 2799 (2015); https://doi.org/10.1007/s00044-015-1331-y
- D. Chaturvedi, S. Zaidi, A.K. Chaturvedi, S. Vaid and A.K. Saxena, Indian J. Chem., 54B, 1019 (2016).
References
R.D.H. Murray, Nat. Prod. Rep., 12, 477 (1995); https://doi.org/10.1039/np9951200477
A. Estévez-Braun and A.G. González, Nat. Prod. Rep., 14, 465 (1997); https://doi.org/10.1039/np9971400465
R. Pratap and V. Ram, Chem. Rev., 114, 10476 (2014); https://doi.org/10.1021/cr500075s
F. Borges, F. Roleira, N. Milhazes, L. Santana and E. Uriarte, Curr. Med. Chem., 12, 887 (2005); https://doi.org/10.2174/0929867053507315
A. Lacy and R. O’Kennedy, Curr. Pharm. Des., 10, 3797 (2004); https://doi.org/10.2174/1381612043382693
I. Kostova, Curr. Med. Chem. Anticancer Agents, 5, 29 (2005); https://doi.org/10.2174/1568011053352550
J. Klenkar and M. Molnar, J. Chem. Pharm. Res., 7, 1223 (2015).
E.A. Fayed, R. Sabour, M.F. Harras and A.B.M. Mehany, Med. Chem. Res., 28, 1284 (2019); https://doi.org/10.1007/s00044-019-02373-x
C.A. Kontogiorgis and D.J. Hadjipavlou-Litina, J. Med. Chem., 48, 6400 (2005); https://doi.org/10.1021/jm0580149
Y. Bansal, P. Sethi and G. Bansal, Med. Chem. Res., 22, 3049 (2013); https://doi.org/10.1007/s00044-012-0321-6
K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas and D.N. Nicolaides, Curr. Pharm. Des., 10, 3813 (2004); https://doi.org/10.2174/1381612043382710
T. Kawate, N. Iwase, M. Shimizu, S.A. Stanley, S. Wellington, E. Kazyanskaya and D.T. Hung, Bioorg. Med. Chem. Lett., 23, 6052 (2013); https://doi.org/10.1016/j.bmcl.2013.09.035
B. Ramesh and K.V. Pugalendi, J. Med. Food, 9, 562 (2006); https://doi.org/10.1089/jmf.2006.9.562
A.P. Dwivedi, S. Kumar, V. Varshney, A.B. Singh, A.K. Srivastava and D.P. Sahu, Bioorg. Med. Chem. Lett., 18, 2301 (2008); https://doi.org/10.1016/j.bmcl.2008.03.003
M.J. Matos, D. Viña, P. Janeiro, F. Borges, L. Santana and E. Uriarte, Bioorg. Med. Chem. Lett., 20, 5157 (2010); https://doi.org/10.1016/j.bmcl.2010.07.013
M.J. Matos, S. Vazquez-Rodriguez, E. Uriarte, L. Santana and D. Viña, Bioorg. Med. Chem. Lett., 21, 4224 (2011); https://doi.org/10.1016/j.bmcl.2011.05.074
M.J. Matos, S. Vilar, R.M. Gonzalez-Franco, E. Uriarte, L. Santana, C. Friedman, N.P. Tatonetti, D. Viña and J.A. Fontenla, Eur. J. Med. Chem., 63, 151 (2013); https://doi.org/10.1016/j.ejmech.2013.02.009
T. Ojala, S. Remes, P. Haansuu, H. Vuorela, R. Hiltunen, K. Haahtela and P. Vuorela, J. Ethnopharmacol., 73, 299 (2000); https://doi.org/10.1016/S0378-8741(00)00279-8
M. Kawase, B. Varu, A. Shah, N. Motohashi, S. Tani, S. Debnath, S. Saito, S. Mahapatra, S.G. Dastidar and A.N. Chakrabarty, Arzneimittelforschung, 51, 67 (2001); https://doi.org/10.1055/s-0031-1300030
P. Curir, F. Galeotti, M. Dolci, E. Barile and V. Lanzotti, J. Nat. Prod., 70, 1668 (2007); https://doi.org/10.1021/np070295v
C. Montagner, S.M. de Souza, C. Groposo, F. Delle Monache, E.F.A. Smânia and A. Smânia Jr., Naturforsch., 63, 21 (2008); https://doi.org/10.1515/znc-2008-1-205
T. Dandena and E. Milkyas, Adv. Pharmacol. Sci., 2019, 5419854 (2019); https://doi.org/10.1155/2019/5419854
J. Sahoo and S.K. Paidesetty, J. Taibah Univ. Med. Sci., 12, 115 (2017); https://doi.org/10.1016/j.jtumed.2017.10.007
M. Tegtmeier and W. Legrum, Arch. Pharm., 331, 143 (1998); https://doi.org/10.1002/(SICI)1521-4184(199804)331:4<143::AIDARDP143>3.0.CO;2-D
V.M. Navarro-García, G. Rojas, M. Avilés, M. Fuentes and G. Zepeda, Mycoses, 54, e569 (2011); https://doi.org/10.1111/j.1439-0507.2010.01993.x
M. Dakanali, E. Roussakis, A.R. Kay and H.E. Katerinopoulos, Tetrahedron Lett., 46, 4193 (2005); https://doi.org/10.1016/j.tetlet.2005.04.059
D. Hadjipavlou-litina, C. Kontogiorgis, E. Pontiki, M. Dakanali, A. Akoumianaki and H.E. Katerinopoulos, J. Enzyme Inhib. Med. Chem., 22, 287 (2007); https://doi.org/10.1080/14756360601073914
Z.M. Nofal, M.I. El-Zahar and S.S. Abd El-Karim, Molecules, 5, 99 (2000); https://doi.org/10.3390/50200099
N. Batra, S. Batra, A. Prateek and B.N. Prakash, Int. J. Pharm., 3, 24 (2012).
A.S. Negi, D. Chaturvedi, A. Gupta, S. Ray, A. Dwivedy and M.M. Singh, Bioorg. Med. Chem. Lett., 15, 99 (2005); https://doi.org/10.1016/j.bmcl.2004.10.031
D. Chaturvedi, S. Ray, A.K. Srivastava and R. Chander, Bioorg. Med. Chem., 16, 2489 (2008); https://doi.org/10.1016/j.bmc.2007.11.062
D. Chaturvedi, A.K. Chaturvedi, N. Mishra and V. Mishra, Org. Chem. Int., 10, 9148 (2012); https://doi.org/10.1039/C2OB26230D
D. Chaturvedi, P.K. Dwivedi, A.K. Chaturvedi, N. Mishra, H.H. Siddiqui and V. Mishra, Med. Chem. Res., 24, 2799 (2015); https://doi.org/10.1007/s00044-015-1331-y
D. Chaturvedi, S. Zaidi, A.K. Chaturvedi, S. Vaid and A.K. Saxena, Indian J. Chem., 54B, 1019 (2016).