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Microwave Synthesis and Biological Evaluation of Coumarins Substituted Furylpyrazolylpyrazoline
Corresponding Author(s) : Parin V. Shaikh
Asian Journal of Chemistry,
Vol. 35 No. 4 (2023): Vol 35 Issue 4, 2023
Abstract
Some new furaylpyrazolylpyrazoline substituted coumarins were synthesized under microwave irradiation. Target compounds were obtained by cyclization of coumarin chalcones with various substituted hydrazine hydrate and arylhydrazines to give the corresponding pyrazoline by Michael addition reaction (1,4-addition on α,β-unsaturated carbonyl group). Establishment of the structure of the synthesized compounds were based on 1H NMR, 13C NMR, IR, mass spectrometry and elemental analysis data. The synthesized compounds were screened for antibacterial in vitro against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi (bacteria) and Aspergillus niger, Candida albicans (fungi) and some of the compounds are acted as potential antimicrobials.
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- K. Martina, G. Cravotto and R.S. Varma, J. Org. Chem., 86, 13857 (2021); https://doi.org/10.1021/acs.joc.1c00865
- A. Lew, P.O. Krutzik, M.E. Hart and R. Chamberlin, J. Comb. Chem., 4, 95 (2002); https://doi.org/10.1021/cc010048o
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- I.-L. Tsai, M.-F. Wun, C.-M. Teng, T. Ishikawa and I.-S. Chen, Phytochemistry, 48, 1377 (1998); https://doi.org/10.1016/S0031-9422(97)00678-X
- B.S. Dawane, S.G. Konda, G.G. Mandawad and B.M. Shaikh, Eur. J. Med. Chem., 45, 387 (2010); https://doi.org/10.1016/j.ejmech.2009.10.015
- M. Amir, H. Kumar and S.A. Khan, Bioorg. Med. Chem. Lett., 18, 918 (2008); https://doi.org/10.1016/j.bmcl.2007.12.043
- S. Bano, K. Javed, S. Ahmad, I. Rathish, S. Singh and M. Alam, Eur. J. Med. Chem., 46, 5763 (2011); https://doi.org/10.1016/j.ejmech.2011.08.015
- Z. Ozdemir, H.B. Kandilci, B. Gumusel, U. Calis and A.A. Bilgin, Eur. J. Med. Chem., 42, 373 (2007); https://doi.org/10.1016/j.ejmech.2006.09.006
- K. Manna and Y.K. Agrawal, Bioorg. Med. Chem. Lett., 19, 2688 (2009); https://doi.org/10.1016/j.bmcl.2009.03.161
- C.V. Patel Ph, D. Thesis, Synthesis and Antimicrobial Activity Study of Nitrogen Containing Heterocyclic Substituted and Heterocyclic Fused Coumarin Derivatives, Sardar Patel University, Vallabh Vidyanagar (2012).
- A. Bischler, Chem. Ber., 25, 2860 (1892).
- G.S.S. Murthi and M. Basak, J. Indian Chem. Soc., 70, 170 (1993).
- M. Bhalla, P.K. Naithani, A. Kumar and T.N. Bhalla, Indian J. Chem., 31B, 183 (1992).
- D.B. Arunakumar, M.N. Kumarswamy, B.P. Nandeshwarappa, G.K. Prakash, B.S. Sherigara and K.M. Mahadevan, Indian J. Chem., 46B, 336 (2007).
- National Committee for Clinical Laboratory Standards (NCCLS), Performance Standards for Antimicrobial Susceptibility Testing; Twelfth Informational Supplement; NCCLS; West Valley Road 940, Suite 1400, Wayne, Pennsylvania, USA M100-S12 (M7) (2002).
References
K. Martina, G. Cravotto and R.S. Varma, J. Org. Chem., 86, 13857 (2021); https://doi.org/10.1021/acs.joc.1c00865
A. Lew, P.O. Krutzik, M.E. Hart and R. Chamberlin, J. Comb. Chem., 4, 95 (2002); https://doi.org/10.1021/cc010048o
P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); https://doi.org/10.1016/S0040-4020(01)00906-1
H. Nishino, T. Okuyama, M. Takata, S. Shibata, H. Tokuda, J. Takayasu, T. Hasegawa, A. Nishino, H. Ueyama and A. Iwashima, Carcinogenesis, 11, 1557 (1990); https://doi.org/10.1093/carcin/11.9.1557
I.-L. Tsai, M.-F. Wun, C.-M. Teng, T. Ishikawa and I.-S. Chen, Phytochemistry, 48, 1377 (1998); https://doi.org/10.1016/S0031-9422(97)00678-X
B.S. Dawane, S.G. Konda, G.G. Mandawad and B.M. Shaikh, Eur. J. Med. Chem., 45, 387 (2010); https://doi.org/10.1016/j.ejmech.2009.10.015
M. Amir, H. Kumar and S.A. Khan, Bioorg. Med. Chem. Lett., 18, 918 (2008); https://doi.org/10.1016/j.bmcl.2007.12.043
S. Bano, K. Javed, S. Ahmad, I. Rathish, S. Singh and M. Alam, Eur. J. Med. Chem., 46, 5763 (2011); https://doi.org/10.1016/j.ejmech.2011.08.015
Z. Ozdemir, H.B. Kandilci, B. Gumusel, U. Calis and A.A. Bilgin, Eur. J. Med. Chem., 42, 373 (2007); https://doi.org/10.1016/j.ejmech.2006.09.006
K. Manna and Y.K. Agrawal, Bioorg. Med. Chem. Lett., 19, 2688 (2009); https://doi.org/10.1016/j.bmcl.2009.03.161
C.V. Patel Ph, D. Thesis, Synthesis and Antimicrobial Activity Study of Nitrogen Containing Heterocyclic Substituted and Heterocyclic Fused Coumarin Derivatives, Sardar Patel University, Vallabh Vidyanagar (2012).
A. Bischler, Chem. Ber., 25, 2860 (1892).
G.S.S. Murthi and M. Basak, J. Indian Chem. Soc., 70, 170 (1993).
M. Bhalla, P.K. Naithani, A. Kumar and T.N. Bhalla, Indian J. Chem., 31B, 183 (1992).
D.B. Arunakumar, M.N. Kumarswamy, B.P. Nandeshwarappa, G.K. Prakash, B.S. Sherigara and K.M. Mahadevan, Indian J. Chem., 46B, 336 (2007).
National Committee for Clinical Laboratory Standards (NCCLS), Performance Standards for Antimicrobial Susceptibility Testing; Twelfth Informational Supplement; NCCLS; West Valley Road 940, Suite 1400, Wayne, Pennsylvania, USA M100-S12 (M7) (2002).