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Synthesis and Antiviral Activities of Some 2,3-Disubstituted Quinazoline Derivatives
Corresponding Author(s) : V.D. Gupta
Asian Journal of Chemistry,
Vol. 27 No. 12 (2015): Vol 27 Issue 12
Abstract
In the search of new leads towards potent antiviral agents 2,3-disubstituted quinazoline derivatives were synthesized and tested for their antiviral activity. Anthranilic acid (1) on treatment with an aromatic acid chloride in pyridine gives 2-aryl-4-oxo-3H-benzoxazines (2) which in turn reacts with p-amino benzoic acid (PABA) to afford 2-aryl-3-p-carboxylatophenyl-4-oxo-3H-quinazolines (3). The compound 3 further reacts with amido alcohols in the presence of conc. H2SO4 resulting 3-[benzoic acid-(3-phthalimidomethyl/3-ethyl-3H-2-phenyl-4-oxo-quinazolinyl/1-ethyl-7-hydroxy-4-methyl-2-oxo-quinolinyl)]-2-aryl-3H-quinazoline-4-ones (4). The resulting compounds 4a-f have been evaluated for their in vitro and in vivo antiviral activity against JEV and HSV type-I. The synthesized compounds were characterized through their physical and chemical analysis. The obtained results can be used as the key step for the building of novel chemical entities with interesting antiviral activity compare with the standard drugs.
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- A.K. Patidar, M. Jeyakandan, A.K. Mobiya and G. Selvam, Int. J. Pharm. Tech. Res., 3, 386 (2011).
- V.K. Tandon, D.B. Yadav, H.K. Maurya, A.K. Chaturvedi and P.K. Shukla, Bioorg. Med. Chem., 14, 6120 (2006); doi:10.1016/j.bmc.2006.04.029.
- D. Hamre, J. Bernstein and R. Donovick, Proc. Soc. Exp. Biol. Med., 73, 275 (1950); doi:10.3181/00379727-73-17652.
- I. Tamm, H.J. Eggers, R. Bablanian, A.F. Wagner and K. Folkers, Nature, 223, 785 (1969); doi:10.1038/223785a0.
- V.K. Pandey and A.K. Aggarwal, Indian J. Chem., 14, 27 (1980).
- V.K. Pandey, D. Mishra and A. Shukla, Indian Drugs, 31, 532 (1994).
- V.K. Pandey, D. Misra, M.N. Joshi and K. Chandra, Pharmacol. Res. Commun., 20, 153 (1988); doi:10.1016/S0031-6989(88)80008-0.
- V.K. Pandey and H.S. Negi, Indian J. Chem., 42B, 206 (2003).
- V.K. Pandey and A. Shukla, Indian J. Chem., 38B, 1381 (1999).
- V.K. Pandey, K.C. Khulbe, G. Saxena, P. Gupta and K. Chandra, Indian Drugs, 30, 513 (1993).
- V.K. Pandey, A.K. Aggarwal, B.M. Gupta and S.K. Raj, Biol. Memoirs, 9, 197 (1984).
- V.K. Pandey and H.S. Negi, Biol. Memoirs, 25, 29 (1999).
- N.W. Hirwe and K.N. Rana, Chem. Ber., 72, 1346 (1939); doi:10.1002/cber.19390720706.
- V.K. Pandey and L.P. Pathak, Indian J. Chem., 44B, 1940 (2005).
- S.R. Buc, J. Am. Chem. Soc., 69, 254 (1947); doi:10.1021/ja01194a024.
- H. von Pechmann and C. Duisberg, Berichte, 16, 19 (1833).
- J. Tschermiac, German Patent, 134979; Chem. Abstr., vol. 2, 1084 (1902).
References
A.K. Patidar, M. Jeyakandan, A.K. Mobiya and G. Selvam, Int. J. Pharm. Tech. Res., 3, 386 (2011).
V.K. Tandon, D.B. Yadav, H.K. Maurya, A.K. Chaturvedi and P.K. Shukla, Bioorg. Med. Chem., 14, 6120 (2006); doi:10.1016/j.bmc.2006.04.029.
D. Hamre, J. Bernstein and R. Donovick, Proc. Soc. Exp. Biol. Med., 73, 275 (1950); doi:10.3181/00379727-73-17652.
I. Tamm, H.J. Eggers, R. Bablanian, A.F. Wagner and K. Folkers, Nature, 223, 785 (1969); doi:10.1038/223785a0.
V.K. Pandey and A.K. Aggarwal, Indian J. Chem., 14, 27 (1980).
V.K. Pandey, D. Mishra and A. Shukla, Indian Drugs, 31, 532 (1994).
V.K. Pandey, D. Misra, M.N. Joshi and K. Chandra, Pharmacol. Res. Commun., 20, 153 (1988); doi:10.1016/S0031-6989(88)80008-0.
V.K. Pandey and H.S. Negi, Indian J. Chem., 42B, 206 (2003).
V.K. Pandey and A. Shukla, Indian J. Chem., 38B, 1381 (1999).
V.K. Pandey, K.C. Khulbe, G. Saxena, P. Gupta and K. Chandra, Indian Drugs, 30, 513 (1993).
V.K. Pandey, A.K. Aggarwal, B.M. Gupta and S.K. Raj, Biol. Memoirs, 9, 197 (1984).
V.K. Pandey and H.S. Negi, Biol. Memoirs, 25, 29 (1999).
N.W. Hirwe and K.N. Rana, Chem. Ber., 72, 1346 (1939); doi:10.1002/cber.19390720706.
V.K. Pandey and L.P. Pathak, Indian J. Chem., 44B, 1940 (2005).
S.R. Buc, J. Am. Chem. Soc., 69, 254 (1947); doi:10.1021/ja01194a024.
H. von Pechmann and C. Duisberg, Berichte, 16, 19 (1833).
J. Tschermiac, German Patent, 134979; Chem. Abstr., vol. 2, 1084 (1902).