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Synthesis, Characterization and Antimicrobial Activity of Some Novel Mannich Bases of Indole-2,3-dione
Corresponding Author(s) : Shobhit Shrivastava
Asian Journal of Chemistry,
Vol. 35 No. 5 (2023): Vol 35 Issue 5, 2023
Abstract
Indole-2,3-dione (isatin) and its 5-substituted derivatives have been reacted with N2-benzylidenepyridine-2,6-diamine to form Schiff bases and the Mannich bases of these compounds were synthesized by reacting them with some secondary amines in presence of formaldehyde. Their chemical structures have been confirmed by mean of their IR and 1H NMR. Antimicrobial screening of synthesized compounds was done by well diffusion method against 4 pathogenic bacteria and 2 pathogenic fungi. Amongst the tested compounds 3-{[6-(benzylideneamino)pyridin-2-yl]imino}-1-(piperazin-1-ylmethyl)-5-fluoro-indolin-2-one and 3-{[6-(benzylideneamino)pyridin-2-yl]-imino}-1-(morpholin-4-ylmethyl)-5-fluoro-indolin-2-one showed significant antibacterial activity and 3-{[6-(benzylideneamino)pyridin-2-yl]imino}-1-(piperazin-1-ylmethyl)-5-methyl-indolin-2-one and 3-{[6-(benzylideneamino)pyridin-2-yl]imino}-1-(morpholin-4-ylmethyl)-5-methyl-indolin-2-one showed the favourable antifungal activity.
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R.P. Gupta, B.N. Yadav and A.K. Srivastava, Proc. Indian Acad. Sci. Sect. A Phys. Sci., 94, 475 (1985); https://doi.org/10.1007/BF02867443
S.N. Pandeya, D. Sriram, G. Nath and E. DeClercq, Eur. J. Pharm. Sci., 9, 25 (1999); https://doi.org/10.1016/S0928-0987(99)00038-X
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Il Farmaco, 54, 624 (1999); https://doi.org/10.1016/S0014-827X(99)00075-0
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Pharm. Acta Helv., 74, 11 (1999); https://doi.org/10.1016/S0031-6865(99)00010-2
S.K. Sridhar, M. Saravanan and A. Ramesh, Eur. J. Med. Chem., 36, 615 (2001); https://doi.org/10.1016/S0223-5234(01)01255-7
S.N. Pandeya, P. Yogeeshwari, D. Sriram and G. Nath, Indian J. Pharm. Sci., 63, 209 (2002).
U.K. Singh, S.N. Pandeya, A. Singh, B.K. Srivastava and M. Pandey, Int. J. Pharm. Sci. Drug Res., 2, 151 (2010).
H. Sachdeva, D. Dwivedi, H.L. Singh and K.P. Sharma, J. Chil. Chem. Soc., 57, 1348 (2012); https://doi.org/10.4067/S0717-97072012000400004
K. Meenakshi, N. Gopal and M. Sarangapani, Int. J. Pharm. Pharm. Sci., 6, 318 (2014).
P. Sinduja, G. Sammaiah and K. Swathi, Int. J. Pharm. Biol. Sci., 8, 214 (2018).
N. Terzioglu, N. Karali, A. Gürsoy, C. Pannecouque, P. Leysen, J. Paeshuyse, J. Neyts, and E. De Clercq, ARKIVOC, 109 (2006); https://doi.org/10.3998/ark.5550190.0007.113
L. Sebastian, A. Desai, M.N. Shampur, Y. Perumal, D. Sriram and R. Vasanthapuram, Virol. J., 5, 64 (2008); https://doi.org/10.1186/1743-422X-5-64
S.K. Sridhar and A. Ramesh, Biol. Pharm. Bull., 24, 1149 (2001); https://doi.org/10.1248/bpb.24.1149
V.A. Muthukumar, S. George and V. Vaidhyalingam, Biol. Pharm. Bull., 31, 1461 (2008); https://doi.org/10.1248/bpb.31.1461
C.R. Prakash, S. Raja and G. Saravanan, Int. J. Pharm. Pharm. Sci., 6, 160 (2014).
P.K. Sharma, S. Balwani, D. Mathur, S. Malhotra, B.K. Singh, A.K. Prasad, C. Len, E.V. Van der Eycken, B. Ghosh, N.G.J. Richards and V.S. Parmar, J. Enzyme Inhib. Med. Chem., 31, 1520 (2016); https://doi.org/10.3109/14756366.2016.1151015
S.S. Jabbar, S.M. Najim and A.A. Fadhil, Int. Res. J. Pharm., 10, 75 (2019); https://doi.org/10.7897/2230-8407.100246
S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Pharm. Sci., 16, 129 (2002); https://doi.org/10.1016/S0928-0987(02)00077-5
A.A. Kulkarni, S.B. Wankhede, N.D. Dhawale, P.B. Yadav, V.V. Deore and I.D. Gonjari, Arab. J. Chem., 10, S184 (2017); https://doi.org/10.1016/j.arabjc.2012.07.020
S.N. Pandeya, D. Sriram, P. Yogeeswari and S. Ananthan, Chemotherapy, 47, 266 (2001); https://doi.org/10.1159/000048533
T. Aboul-Fadl and A.S. Fayzah Bin-Jubair, Int. J. Res. Pharm. Sci., 1, 113 (2010).
N. Karali, A. Gursoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Ozbey, V. Kovalishyn and A. Dimoglo, Bioorg. Med. Chem., 15, 5888 (2007); https://doi.org/10.1016/j.bmc.2007.05.063
D. Sriram, A. Aubry, P. Yogeeswari and L.M. Fisher, Bioorg. Med. Chem. Lett., 16, 2982 (2006); https://doi.org/10.1016/j.bmcl.2006.02.065
S.K. Sahu, M.A. Azam, M. Banerjee, S. Acharrya, C.C. Behera and S. Si, J. Braz. Chem. Soc., 19, 963 (2008); https://doi.org/10.1590/S0103-50532008000500023
N. Karali, N. Terzioglu and A. Gürsoy, Arch. Pharm., 335, 374 (2002); https://doi.org/10.1002/1521-4184(200211)335:8<374::AID-ARDP374>3.0.CO;2-K
A.T. Taher, N.A. Khalil and E.M. Ahmed, Arch. Pharm. Res., 34, 1615 (2011); https://doi.org/10.1007/s12272-011-1005-3
S.A. Ibrahim and T. Elsaman, J. Pharm. Res. Int., 21, 1 (2018).
S.N. Pandeya, D. Sriram and E. De Clercq, Indian J. Pharm. Sci., 60, 207 (1998).
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Indian J. Pharm. Sci., 61, 358 (1999).
S.N. Pandeya, P. Yogeeswari, D. Sriram, E. de Clercq, C. Pannecouque and M. Witvrouw, Chemotherapy, 45, 192 (1999); https://doi.org/10.1159/000007182
S.N. Pandeya, D. Sriram, G. Nath and E. de Clercq, Arzneimittel-forschung, 50, 55 (2000); https://doi.org/10.1055/s-0031-1300164
A.W. Bauer, W.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45(4_ts), 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493