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Synthesis, Spectral Studies and Antibacterial Activity of 3-(4-Phenyl-2,3-dihydro-1,5-benzodiazepin-2-yl)chromone
Corresponding Author(s) : Vinay Prabha Sharma
Asian Journal of Chemistry,
Vol. 26 No. 13 (2014): Vol 26 Issue 13
Abstract
3-(4-Phenyl-2,3-dihydro-1,5-benzodiazepin-2-yl)chromone (PHBDC) has been synthesized by reacting 1-phenyl-3-(chromon-3-yl)-2-propene-1-one (chalcone) with o-phenylenediamine. Structures of chalcone as well as PHBDC were established on the basis of elemental analysis, IR and PMR spectral studies. 3-(4-Phenyl-2,3-dihydro-1,5-benzodiazepin-2-yl)chromone has been found to be antibacterial against bacillus bacteria some of which cause food poisoning, anthrax (a malignant boil), etc.
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- (a) V.P. Sharma, P. Kumar and M. Sharma, Asian J. Chem., 23, 4616 (2011); (b) V.B. Halnor, N. R. Dalvi, N. S. Joshi, C. H. Gill and B. K. Karale, Indian J. Chem., 45 B, 288 (2006).
- R. Purnik, Y. Jay Prakesh Rao and G.J. Kurupadam, Indian J. Chem., 41B, 869 (2002).
- S.M. Bhalekar and H.M. Prab, Indian J. Heterocycl. Chem., 17, 285 (2008).
- M. Yamada and K. Koyama, Japan Kokai Tokyo Koha Jp, 07,165,748 (1995); Chem. Abstr., 124, 7336a (1996).
- V. Gupta and U. Mishra, Indian J. Heterocycl. Chem., 17, 281 (2008).
- R.G. Naik, S.L. Kattige, S.A.V. Bhat, B. Alreja, N.J. Desouza and R.H. Rupp, Tetrahedron Lett., 44, 2081 (1988); doi:10.1016/S0040-4020(01)90352-7.
- C. P. Garg, V. P. Sharma and R.P. Kapoor, Indian J. Chem., 24B, 1197 (1985).
- C.P. Garg, V.P. Sharma, V. Chhabra and R.P. Kapoor, Indian J. Chem., 27B, 469 (1988).
- G.S. Barsoum and M.R. Kenawy, Am. Heart, 47, 297 (1954); doi:10.1016/0002-8703(54)90256-2.
- E. Kohlstaedt and K.H. Klinger, Ger. Patent, 1,018,874; Chem. Abstr., 54, 5700 (1960).
- D. Molho, E. Boschetti and L. Fontiane, Fr. M. 2472; Chem. Abstr., 61, 11975 (1964).
- R.I. Fryer, Bicyclic Diazapines in Chemistry of Heterocyclic Compounds, 50, E. Taylor, Ed. Wiley (1992), Chapter II, Chem. Abstr., 73, 100054 w (1970).
- L.H. Sternbach, J. Med. Chem., 22, 1 (1979); doi:10.1021/jm00187a001.
- T.L. Gilchrist, Heterocyclic Chemistry, John Wiley & Sons Inc., New York, p. 346 (1991).
- A. Nohara, T. Umetani and Y. Sanno, Tetrahedron, 30, 3553 (1974); doi:10.1016/S0040-4020(01)97034-6.
- A.G. Nikalje, R.D. Ingle, V.E. Bhingolikar and R.A. Mane, Indian J. Heterocycl. Chem., 13, 37 (2003).
References
(a) V.P. Sharma, P. Kumar and M. Sharma, Asian J. Chem., 23, 4616 (2011); (b) V.B. Halnor, N. R. Dalvi, N. S. Joshi, C. H. Gill and B. K. Karale, Indian J. Chem., 45 B, 288 (2006).
R. Purnik, Y. Jay Prakesh Rao and G.J. Kurupadam, Indian J. Chem., 41B, 869 (2002).
S.M. Bhalekar and H.M. Prab, Indian J. Heterocycl. Chem., 17, 285 (2008).
M. Yamada and K. Koyama, Japan Kokai Tokyo Koha Jp, 07,165,748 (1995); Chem. Abstr., 124, 7336a (1996).
V. Gupta and U. Mishra, Indian J. Heterocycl. Chem., 17, 281 (2008).
R.G. Naik, S.L. Kattige, S.A.V. Bhat, B. Alreja, N.J. Desouza and R.H. Rupp, Tetrahedron Lett., 44, 2081 (1988); doi:10.1016/S0040-4020(01)90352-7.
C. P. Garg, V. P. Sharma and R.P. Kapoor, Indian J. Chem., 24B, 1197 (1985).
C.P. Garg, V.P. Sharma, V. Chhabra and R.P. Kapoor, Indian J. Chem., 27B, 469 (1988).
G.S. Barsoum and M.R. Kenawy, Am. Heart, 47, 297 (1954); doi:10.1016/0002-8703(54)90256-2.
E. Kohlstaedt and K.H. Klinger, Ger. Patent, 1,018,874; Chem. Abstr., 54, 5700 (1960).
D. Molho, E. Boschetti and L. Fontiane, Fr. M. 2472; Chem. Abstr., 61, 11975 (1964).
R.I. Fryer, Bicyclic Diazapines in Chemistry of Heterocyclic Compounds, 50, E. Taylor, Ed. Wiley (1992), Chapter II, Chem. Abstr., 73, 100054 w (1970).
L.H. Sternbach, J. Med. Chem., 22, 1 (1979); doi:10.1021/jm00187a001.
T.L. Gilchrist, Heterocyclic Chemistry, John Wiley & Sons Inc., New York, p. 346 (1991).
A. Nohara, T. Umetani and Y. Sanno, Tetrahedron, 30, 3553 (1974); doi:10.1016/S0040-4020(01)97034-6.
A.G. Nikalje, R.D. Ingle, V.E. Bhingolikar and R.A. Mane, Indian J. Heterocycl. Chem., 13, 37 (2003).