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Synthesis of Potential Biologically Active 4,5-Dimethoxy-2-[3-oxo-3-phenylprop-1-en-1-yl]benzene Sulfonic Acid Derivatives
Corresponding Author(s) : Bilal Shahid
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
A series of potential biologically active 4,5-dimethoxy-2-[3-oxo-3-phenylprop-1-en-1-yl]benzenesulfonamides was synthesized. 3,4-Dimethoxybenzaldehyde was condensed with acetophenone followed by its chlorosulfonation to get 4,5-dimethoxy-2-[3-oxo-3-phenylprop-1-en-1-yl]benzenesulfonyl chloride, which was further reacted with a number of amines and hydrazides to get the 4,5-dimethoxy-2-[3-oxo-3-phenylprop-1-en-1-yl]benzenesulfonic acid derivatives. All the synthesized compounds were subjected to preliminary evaluation for their antibacterial activity against selected strains of gram positive and gram negative bacteria. Some of the assayed compounds showed marked activity.
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- N. Shimada, T. Aoki, S. Sato, Y. Nakamura, S. Tabata and S. Ayabe, Plant Physiol., 131, 941 (2003).
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References
N. Shimada, T. Aoki, S. Sato, Y. Nakamura, S. Tabata and S. Ayabe, Plant Physiol., 131, 941 (2003).
T. Hussain, H.L. Siddiqui, M. Zia-ur-Rehman, M.M. Yasinzai and M. Parvez, Eur. J. Med. Chem., 44, 4654 (2009).
S. Ducki, IDrugs, 10, 42 (2007).
N.J. Lawrence and A. T. McGown, Curr. Pharm. Des., 11, 1679 (2005).
Z. Nowakowska, Eur. J. Med. Chem., 42, 125 (2007).
J.R. Dimmock, D.W. Elias, M.A. Beazely and N.M. Kandepu, Curr. Med. Chem., 6, 1125 (1999).
H.H. Ko, L.T. Tsao, K.L. Yu, C.T. Liu, J.P. Wang and C.N. Lin, Bioorg. Med. Chem., 11, 105 (2003).
A.M. Deshpande, N.P. Argade, A.A. Natu and J. Eckman, Bioorg. Med. Chem., 7, 1237 (1999).
J. Rajas, J.M. Paya, J.N. Dominguez and M.L. Ferrandiz, Bioorg. Med. Chem. Lett., 12, 1951 (2002).
S. Khatib, O. Nerya, R. Musa, M. Shmnel, S. Tamir and J. Vaya, Bioorg. Med. Chem., 13, 433 (2005).
F. Severi, S. Benvenuti, L. Costantino, G. Vampa, M. Melegari and L. Antolini, Eur. J. Med. Chem., 33, 859 (1998).
S. Padhye, A. Ahmad, N. Oswal and F. H Sarkar, J. Hematol. Oncol., 2, 38 (2009).
Y. Satomi, Int. J. Cancer, 55, 506 (1993)
S. Yamamoto, E. Aizu, H. Jiang, T. Nakadate, I. Kiyoto, J.C.Wang and R. Kato, Carcinogenesis, 12, 317 (1991).
C.A. Calliste, J.C. Le Bail, P. Trouillas, C. Pouget, G. Habrioux, A.J. Chulia and J.L. Duroux, Anti-cancer Res., 21, 3949 (2001).
M. Liu, P. Wilairat, S.L. Croft, A. Lay-Choo Tan and M.-L. Go, Bioorg. Med. Chem., 11, 2729 (2003).
J.N. Dominguez, J.E. Charis, G. Lobo, N.G. de Domínguez, M.M. Moreno, F. Riggione, E. Sanchez, J. Olson and P.J. Rosenthal, Eur. J. Med. Chem., 36, 555 (2001).
N. Ahmed, M. Zia-ur-Rehman, H.L. Siddiqui, M.F. Ullah and M. Parvez, Eur. J. Med. Chem., 46, 2368 (2009).
W.D. Seo, J.H. Kim, J.E. Kang, H.W. Ryu, M.J.C. Long, H.S. Lee, M.S. Yang and K.H. Park, Bioorg. Med. Chem. Lett., 15, 5514 (2005).
J.N. Domínguez, C. León, J. Rodrigues, N.G. de Domínguez, J. Gut and P. J. Rosenthal, Farmaco, 60, 307 (2005).
V. Shettigar, J. B.-J. Teh, H.-K. Fun, I. A. Razak, P. S. Patil and S. M. Dharmaprakash, Acta Cryst., E62, o4646 (2006).
J.G. Colle, J.P. Duguid, A.G. Fraser and B.P. Marmion, in eds.: T.J. Mackie and J.E. McCartney, Practical Medical Biology, Churchill Livingstone, London, UK, Vol. 13 (1989).
H. Hanel and W. Raether, Mycoses, 31, 148 (1988).
C. Booth, in eds.: J.R. Norris and D.W. Ribbons, Methods in Microbiology, Academic Press, London, New York, Vol. IV, p. 49-94 (1977).