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Efficient Synthesis of 5(4H)-Imidazolones and in vitro Antifungal Activity Studies Against Selected Phytopathogens
Corresponding Author(s) : Christopher Voosala
Asian Journal of Chemistry,
Vol. 26 No. 10 (2014): Vol 26 Issue 10
Abstract
A series of five new 1-(substituted phenyl)-2-phenyl-4-(substituted benzylidine)imidazole-5-one derivatives (or) 5(4H)-imidazolones have been synthesized adopting SiO2, Al2O3-90 and Y-faujasite (Y-H type) zeolite as catalysts. These compounds were assayed for their antifungal activity on three different selected phytopathogens which disparately affects the Jowar crop (Sorghum vulgare) of poaceae family. Among the screened target molecules, compound 18 exhibited potent inhibitory activity compared to the standard drug bavistine, which is worth for further investigation.
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- A.C. Cuckler, A.B. Kupferberg and N. Hillman, Antibiot. Chemother., 5, 540 (1955).
- H.K. Urman, O. Bulay, D.B. Clayson and P. Shubik, Cancer Lett., 1, 69 (1975); doi:10.1016/S0304-3835(75)95362-8.
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- H. Lehr, S. Karlan and M.W. Goldberg, J. Am. Chem. Soc., 75, 3640 (1953); doi:10.1021/ja01111a011.
- L.D.S. Yadav and S. Singh, Synthesis, 63 (2003); doi:10.1055/s-2003-36257.
- Z. Hell, A. Cwik, Z. Finta and Z. Horváth, J. Mol. Catal. A, 184, 191 (2002); doi:10.1016/S1381-1169(01)00518-0.
- R. Roy, Science, 238, 1664 (1987); doi:10.1126/science.238.4834.1664.
- A.L. McKenna in Kirk-othmer, Encyclopedia of Chemical Technology, Aluminium Carboxylates, Wiley, New York, vol. 2, p. 273 (1991).
- Y.L.N. Murthy, V. Christopher, U.V. Prasad, P.B. Bisht, D.V. Ramanaih, B.S. Kalanoor and S.A. Ali, Synth. Met., 160, 535 (2010); doi:10.1016/j.synthmet.2009.11.029.
- K. Smith, M. Butters and B. Nay, Synthesis, 1985, 1157 (1985); doi:10.1055/s-1985-31462.
- P. Ratnasamy, A.P. Singh and S. Sharma, Appl. Catal. A, 135, 25 (1996); doi:10.1016/0926-860X(95)00210-3.
- S.A. Siddiqui, S.R. Bhusare and D.V. Jarikote, Bull. Korean Chem. Soc., 22, 1033 (2001).
- C.P. Pauli and P. Bazerque, Acta Biol. Med. Exper., 15, 113 (1990).]
- P.R. Murray, E.J. Baron and M.A. Pfaller, Manual of clinical Microbiology, ASM Press, Washington D.C., edn 6 (1995).
References
A.C. Cuckler, A.B. Kupferberg and N. Hillman, Antibiot. Chemother., 5, 540 (1955).
H.K. Urman, O. Bulay, D.B. Clayson and P. Shubik, Cancer Lett., 1, 69 (1975); doi:10.1016/S0304-3835(75)95362-8.
W.B. Wright Jr. and H.J. Brabander, J. Org. Chem., 26, 4051 (1961); doi:10.1021/jo01068a098.
V. Niedbalia and I. Buctteher, Chem. Abstr., 94, 15732 (1981).
K.J. Shaw, P.W. Erhardt, A.A. Hagedom, C.A. Pease, W.R. Ingebretsen and J.R. Wiggins, J. Med. Chem., 35, 1267 (1992); doi:10.1021/jm00085a014.
A. Nefzi, J.M. Ostresh and R.A. Houghten, Chem. Rev., 97, 449 (1997); doi:10.1021/cr960010b.
J.W. Cornforth and H.T. Huang, J. Chem. Soc., 731 (1948); doi:10.1039/jr9480000731.
H. Lehr, S. Karlan and M.W. Goldberg, J. Am. Chem. Soc., 75, 3640 (1953); doi:10.1021/ja01111a011.
L.D.S. Yadav and S. Singh, Synthesis, 63 (2003); doi:10.1055/s-2003-36257.
Z. Hell, A. Cwik, Z. Finta and Z. Horváth, J. Mol. Catal. A, 184, 191 (2002); doi:10.1016/S1381-1169(01)00518-0.
R. Roy, Science, 238, 1664 (1987); doi:10.1126/science.238.4834.1664.
A.L. McKenna in Kirk-othmer, Encyclopedia of Chemical Technology, Aluminium Carboxylates, Wiley, New York, vol. 2, p. 273 (1991).
Y.L.N. Murthy, V. Christopher, U.V. Prasad, P.B. Bisht, D.V. Ramanaih, B.S. Kalanoor and S.A. Ali, Synth. Met., 160, 535 (2010); doi:10.1016/j.synthmet.2009.11.029.
K. Smith, M. Butters and B. Nay, Synthesis, 1985, 1157 (1985); doi:10.1055/s-1985-31462.
P. Ratnasamy, A.P. Singh and S. Sharma, Appl. Catal. A, 135, 25 (1996); doi:10.1016/0926-860X(95)00210-3.
S.A. Siddiqui, S.R. Bhusare and D.V. Jarikote, Bull. Korean Chem. Soc., 22, 1033 (2001).
C.P. Pauli and P. Bazerque, Acta Biol. Med. Exper., 15, 113 (1990).]
P.R. Murray, E.J. Baron and M.A. Pfaller, Manual of clinical Microbiology, ASM Press, Washington D.C., edn 6 (1995).