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Abstract
In the present paper, we report herein synthesis of 5-aryl-3-(4-chloro- 6-methyl-2H-pyran-2-on-3-yl)-1-phenylpyrazoles. All the compounds were characterized by spectroscopic methods such as IR, NMR and analytic methods and evaluated for their antibacterial and antifungal activities. It is found that some of these compounds are potent antimicrobial agents.
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References
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- M. Shahar Yar, M.A. Bakht, A.A. Siddiqui, M.M. Abdullah and E. De Clercq, J. Enzyme Inhib. Med. Chem., 24, 876 (2009); https://doi.org/10.1080/14756360802447917.
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- S.S. Korgaokar, P.H. Patil, M.J. Shah and H.H. Parekh, Indian J. Pharm. Sci., 58, 222 (1996).
- R.H. Udupi, A.S. Kushnoor and A.R. Bhat, Indian J. Heterocycl. Chem., 8, 63 (1998).
- A. Burguete, E. Pontiki, D. Hadjipavlou-Litina, R. Villar, E. Vicente, B. Solano, S. Ancizu, S. Pérez-Silanes, I. Aldana and A. Monge, Bioorg. Med. Chem. Lett., 17, 6439 (2007); https://doi.org/10.1016/j.bmcl.2007.10.002.
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- Z.Y. Lu, W.G. Zhu, Q. Jiang and M.G. Xie, Chin. Chem. Lett., 10, 679 (1999).
- S.S. Parmar, B.R. Pandey, C. Dwivedi and R.D. Harbison, J. Pharm. Sci., 63, 1152 (1974); https://doi.org/10.1002/jps.2600630730.
- E. Takabatake, R. Kodama, Y. Tanaka, R. Dohmori, H. Tachizawa and T. Naito, Chem. Pharm. Bull. (Tokyo), 18, 1900 (1970); https://doi.org/10.1248/cpb.18.1900.
- K.R. Aneja, C. Sharma and R. Joshi, Int. J. Ortorhinolaryngol., 74, 604 (2010); https://doi.org/10.1016/j.ijporl.2010.03.001.
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- (a) L.S. Goodman and A. Gilman, The Pharmacological Basis of Therapeutics, Macmillan, New York (1980); (b) M. Wachter and M. Ferro, 1,5-Diaryl-3-substitutedPyrazoles Pharmaceutical Compositions and Use, US Patent 4826868 (1989).
- (a) H.V. Secor and J.F. DeBardeleben, J. Med. Chem., 14, 997 (1971); https://doi.org/10.1021/jm00292a032. (b) V.J. Bauer, H.P. Dalalian, W.J. Fanshawe, S.R. Safir, E.C. Tocus and C.R. Boshart, J. Med. Chem., 11, 981 (1968); https://doi.org/10.1021/jm00311a015.
- O. Prakash, A. Kumar, M. Kinger and S.P. Singh, Indian J. Chem., 44B, 456 (2006).
- G.K. Sabitha, G.S.K. Kumar Reddy, C.S. Reddy, N. Fatima and J.S. Yadav, Synthesis, 1267 (2003); https://doi.org/10.1055/s-2003-39410.
- N. Nakamichi, Y. Kawashita and M. Hayashi, Org. Lett., 4, 3955 (2002); https://doi.org/10.1021/ol0268135.
- J.N. Shah and C.K. Shah, J. Org. Chem., 43, 1266 (1978); https://doi.org/10.1021/jo00400a060.
- I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1967); https://doi.org/10.1016/0040-4020(68)88080-9.
- P.D. Lokhande, B.Y. Waghamare and S.S. Sakate, Indian J. Chem., 44B, 2338 (2005).
References
P. Manoj Kumar, R. Ajay Kumar and T.K. Ravi, Indian J. Pharm. Sci., 67, 755 (2005).
M. Shahar Yar, M.A. Bakht, A.A. Siddiqui, M.M. Abdullah and E. De Clercq, J. Enzyme Inhib. Med. Chem., 24, 876 (2009); https://doi.org/10.1080/14756360802447917.
M.I. Hussain and S. Shukla, Indian J. Chem., 25B, 983 (1986).
S.B. jadhav, R.A. shastri, K.V. Gaikwad and S.V. Gaikwad, E-J. Chem., 6, 183 (2009); https://doi.org/10.1155/2009/361564.
H. Kawazura, Y. Takahashi, Y. Shiga, F. Shimada, N. Ohto and A. Tamura, Jpn. J. Pharmacol., 73, 317 (1997); https://doi.org/10.1254/jjp.73.317.
F.F. Barsoum, H.M. Hosni and A.S. Girgis, Bioorg. Med. Chem., 14, 3929 (2006); https://doi.org/10.1016/j.bmc.2006.01.042.
S.S. Korgaokar, P.H. Patil, M.J. Shah and H.H. Parekh, Indian J. Pharm. Sci., 58, 222 (1996).
R.H. Udupi, A.S. Kushnoor and A.R. Bhat, Indian J. Heterocycl. Chem., 8, 63 (1998).
A. Burguete, E. Pontiki, D. Hadjipavlou-Litina, R. Villar, E. Vicente, B. Solano, S. Ancizu, S. Pérez-Silanes, I. Aldana and A. Monge, Bioorg. Med. Chem. Lett., 17, 6439 (2007); https://doi.org/10.1016/j.bmcl.2007.10.002.
A.A. Siddiqui, M.A. Rahman, M. Shaharyar and R. Mishra, Chem. Sci. J., 8, 1 (2010).
Z. Ozdemir, H.B. Kandilci, B. Gümüsel, U. Çalis and A.A. Bilgin, Eur. J. Med. Chem., 42, 373 (2007); https://doi.org/10.1016/j.ejmech.2006.09.006.
V.H. Babu, C.H. Sridevi, A. Joseph and K.K. Srinivasan, Indian J. Pharm. Sci., 69, 470 (2007); https://doi.org/10.4103/0250-474X.34569.
Z.Y. Lu, W.G. Zhu, Q. Jiang and M.G. Xie, Chin. Chem. Lett., 10, 679 (1999).
S.S. Parmar, B.R. Pandey, C. Dwivedi and R.D. Harbison, J. Pharm. Sci., 63, 1152 (1974); https://doi.org/10.1002/jps.2600630730.
E. Takabatake, R. Kodama, Y. Tanaka, R. Dohmori, H. Tachizawa and T. Naito, Chem. Pharm. Bull. (Tokyo), 18, 1900 (1970); https://doi.org/10.1248/cpb.18.1900.
K.R. Aneja, C. Sharma and R. Joshi, Int. J. Ortorhinolaryngol., 74, 604 (2010); https://doi.org/10.1016/j.ijporl.2010.03.001.
I. Ahmad and A.J. Beg, J. Ethnopharmacol., 74, 113 (2001); https://doi.org/10.1016/S0378-8741(00)00335-4.
J.M. Andrews, J. Antimicrob. Chemother., 48(suppl 1), 5 (2001); https://doi.org/10.1093/jac/48.suppl_1.5.
NCCLS, Method for Dilution Antimicrobial Susceptibility Test for Bacteria that Grow Aerobically Approved Standards, National Committee for Clinical Standards, PA, Villanova, edn 5 (2000).
S.K.S. Al-Burtamani, M.O. Fatope, R.G. Marwah, A.K. Onifade and S.H. Al-Saidi, J. Ethnopharmacol., 96, 107 (2005); https://doi.org/10.1016/j.jep.2004.08.039.
D. Kumar and S.P. Singh, Heterocycles, 63, 145 (2004); https://doi.org/10.3987/REV-03-569.
(a) L.S. Goodman and A. Gilman, The Pharmacological Basis of Therapeutics, Macmillan, New York (1980); (b) M. Wachter and M. Ferro, 1,5-Diaryl-3-substitutedPyrazoles Pharmaceutical Compositions and Use, US Patent 4826868 (1989).
(a) H.V. Secor and J.F. DeBardeleben, J. Med. Chem., 14, 997 (1971); https://doi.org/10.1021/jm00292a032. (b) V.J. Bauer, H.P. Dalalian, W.J. Fanshawe, S.R. Safir, E.C. Tocus and C.R. Boshart, J. Med. Chem., 11, 981 (1968); https://doi.org/10.1021/jm00311a015.
O. Prakash, A. Kumar, M. Kinger and S.P. Singh, Indian J. Chem., 44B, 456 (2006).
G.K. Sabitha, G.S.K. Kumar Reddy, C.S. Reddy, N. Fatima and J.S. Yadav, Synthesis, 1267 (2003); https://doi.org/10.1055/s-2003-39410.
N. Nakamichi, Y. Kawashita and M. Hayashi, Org. Lett., 4, 3955 (2002); https://doi.org/10.1021/ol0268135.
J.N. Shah and C.K. Shah, J. Org. Chem., 43, 1266 (1978); https://doi.org/10.1021/jo00400a060.
I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1967); https://doi.org/10.1016/0040-4020(68)88080-9.
P.D. Lokhande, B.Y. Waghamare and S.S. Sakate, Indian J. Chem., 44B, 2338 (2005).