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Synthesis, Characterization and Bioevaluation of (Z)-4-Substituted phenyl-2-((2-oxoindolin-3-ylidene)aminocyclopent-1-ene carbodithioate) Derivatives from 2-Aminocyclopent-1-ene Carbodithioic Acid
Corresponding Author(s) : Y.L.N. Murthy
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
A series of oxoindoline derivatives 6(a-e) have been synthesized. Treatment of cyclopentanone (1) with carbon disulphide (2) in liq. NH3 yielded 2-amino-cyclopent-1-enecarbodithioic acid (3) which on further treatment with isatin (4) in ethanol under reflux conditions for 2 h gave (Z)-2-(2-oxoindolin)-aminocyclopentene carbodithioic acid (5). Compound 5 was treated with different 1,4 diaryl substituents in THF resulted the formation of the target molecule viz., oxoindoline derivatives 6(a-e). These compounds were evaluated in vitro antimicrobial activities by agar well dilution method. Oxoindoline derivatives exhibited the broad spectrum of antibacterial activity (compounds 3, 5, 6a, 6c, 6e) and mild activity (6b and 6d), besides potent antifungal activity.
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- J.F.M. Silva, S.J. Garden and A.C. Pinto, J. Braz. Chem. Soc., 12, 273 (2001); doi:10.1590/S0103-50532001000300002.
- M. Farghaly, B.F. Abdel-Wahab and E.M. Ahmed, Chem. Heterocycl. Comp., 45, 539 (2009); doi:10.1007/s10593-009-0301-z .
- S.N. Pandeya, Pharm. Turc., 40, 33 (1998).
- M. Sarangapani, Indian J. Heterocycl. Chem., 3, 257 (1994).
- R.S. Varma and W.L. Nobles, J. Pharm. Sci., 64, 881 (1975); doi:10.1002/jps.2600640539.
- S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Farmaco, 54, 624 (1999); doi:10.1016/S0014-827X(99)00075-0.
- S.P. Singh and S.K. Shukla, Curr. Sci., 52, 766 (1983).
- S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Eur. J. Med. Chem., 35, 249 (2000); doi:10.1016/S0223-5234(00)00125-2.
- S.N. Pandeya, P. Yogeeswari, D. Sriram, E. de Clercq, C. Pannecouque and M. Witvrouw, Chemotherapy, 45, 192 (1999); doi:10.1159/000007182.
- G. Chen, Y. Wang, X.J. Hao, S.Z. Mu and Q.Y. Sun, Chem. Cent. J., 5, 37 (2011); doi:10.1186/1752-153X-5-37.
- C. David and T. Marie, Chem. Abstr., 124, 343271 (1996).
- M. Sarangapani, Indian J. Pharm. Sci., 59, 105 (1997).
- S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Med. Chem., 16, 129 (2002); doi:10.1016/S0928-0987(02)00077-5.
- M. Varma, S.N. Pandeya and K.N. Singh, Acta Pharm., 54, 49 (2004).
- S.K. Sridhar, Indian Drugs, 38, 174 (2011).
References
J.F.M. Silva, S.J. Garden and A.C. Pinto, J. Braz. Chem. Soc., 12, 273 (2001); doi:10.1590/S0103-50532001000300002.
M. Farghaly, B.F. Abdel-Wahab and E.M. Ahmed, Chem. Heterocycl. Comp., 45, 539 (2009); doi:10.1007/s10593-009-0301-z .
S.N. Pandeya, Pharm. Turc., 40, 33 (1998).
M. Sarangapani, Indian J. Heterocycl. Chem., 3, 257 (1994).
R.S. Varma and W.L. Nobles, J. Pharm. Sci., 64, 881 (1975); doi:10.1002/jps.2600640539.
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Farmaco, 54, 624 (1999); doi:10.1016/S0014-827X(99)00075-0.
S.P. Singh and S.K. Shukla, Curr. Sci., 52, 766 (1983).
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Eur. J. Med. Chem., 35, 249 (2000); doi:10.1016/S0223-5234(00)00125-2.
S.N. Pandeya, P. Yogeeswari, D. Sriram, E. de Clercq, C. Pannecouque and M. Witvrouw, Chemotherapy, 45, 192 (1999); doi:10.1159/000007182.
G. Chen, Y. Wang, X.J. Hao, S.Z. Mu and Q.Y. Sun, Chem. Cent. J., 5, 37 (2011); doi:10.1186/1752-153X-5-37.
C. David and T. Marie, Chem. Abstr., 124, 343271 (1996).
M. Sarangapani, Indian J. Pharm. Sci., 59, 105 (1997).
S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Med. Chem., 16, 129 (2002); doi:10.1016/S0928-0987(02)00077-5.
M. Varma, S.N. Pandeya and K.N. Singh, Acta Pharm., 54, 49 (2004).
S.K. Sridhar, Indian Drugs, 38, 174 (2011).