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Sulfadiazine Guanidyl Derivatives: Synthesis, Characterization and Docking Studies for Potential Antituberculosis Agents
Corresponding Author(s) : Mahesh Bhat
Asian Journal of Chemistry,
Vol. 30 No. 9 (2018): Vol 30 Issue 9
Abstract
Due to the wide range of pharmacological and biological activities, guanidine considered as one of the attractive pharmacophores. The presence of -CN3 group in guanidine compounds makes them to have efficient affinity towards various substituents with wide range of biochemical activities. In the present study, novel sulfadiazine guanidyl derivatives were synthesized and characterized by FT-IR, LC-MS and NMR spectral studies. The synthesized compounds were screened for antituberculosis activity and molecular docking study with InhA proteins was carried out. It was found that the compounds with electron donating groups exhibited superior activity.
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- Y. Yamamoto and S. Kojima, Synthesis and Chemistry of Guanidine Derivatives: The Chemistry of Amidines and Imidates, John Wiley & Sons Ltd., vol. 2 (1991)
- D. Lednicer and L.A. Mitscher, eds., The Organic Chemistry of Drugs Synthesis; Wiley: New York, vol. II, (1980).
- R.G.S. Berlinck, Fortschr. Chem. Org. Naturst., 66, 119 (1995); https://doi.org/10.1007/978-3-7091-9363-1_2.
- K. Burgess, ed., Solid-Phase Organic Synthesis; John Wiley & Sons: New York, USA (2000).
- G.J. Durant, Chem. Soc. Rev., 14, 375 (1985); https://doi.org/10.1039/cs9851400375.
- A. Echavarren, A. Galan, J.M. Lehn and J. De Mendoza, J. Am. Chem. Soc., 111, 4994 (1989); https://doi.org/10.1021/ja00195a071.
- O. Kamoda, K. Anzai, J. Mizoguchi, M. Shiojiri, T. Yanagi, T. Nishino and S. Kamiya, Antimicrob. Agents Chemother., 50, 3062 (2006); https://doi.org/10.1128/AAC.00036-06.
- M. Bhat and S.L. Belagali, Res. Chem. Intermed., 42, 6195 (2016); https://doi.org/10.1007/s11164-016-2454-6.
- M. Bhat, S.L. Belagali and D.C. Shyamala, The Natural Products J., 7, 286 (2017); https://doi.org/10.2174/2210315507666170530091940.
- M. Bhat and S.L. Belagali, Anti-Infective Agents, 16, 1 (2018); https://doi.org/10.2174/2211352516666180425151720.
- M. Varga, Textbook of Rabbit Medicine, Elsevier Health: UK, edn 2, pp. 137-177 (2014).
- V.P. Arcangelo and A.M. Peterson, Pharmacotherapeutics for Advanced Practice: A Practical Approach, Lippincott Williams & Wilkins, vol. 536, pp 959 (2006).
- M.C.S. Lourenco, M.V.N. de Souza, A.C. Pinheiro, M. de L. Ferreira, R.S.B. Gonçalves, T.C.M. Nogueira and M.A. Peralta, ARKIVOC, 181 (2007); https://doi.org/10.3998/ark.5550190.0008.f18.
- M.K. Raj, C. Balachandran, V. Duraipandiyan, P. Agastian, S. Ignacimuthu and A. Vijayakumar, Med. Chem. Res., 22, 3823 (2013); https://doi.org/10.1007/s00044-012-0393-3.
- M. Fathimunnisa, H. Manikandan, K. Neelakandan, N. Rajendra Prasad, S. Selvanayagam and B. Sridhar, J. Mol. Struct., 1122, 205 (2016); https://doi.org/10.1016/j.molstruc.2016.06.012.
References
Y. Yamamoto and S. Kojima, Synthesis and Chemistry of Guanidine Derivatives: The Chemistry of Amidines and Imidates, John Wiley & Sons Ltd., vol. 2 (1991)
D. Lednicer and L.A. Mitscher, eds., The Organic Chemistry of Drugs Synthesis; Wiley: New York, vol. II, (1980).
R.G.S. Berlinck, Fortschr. Chem. Org. Naturst., 66, 119 (1995); https://doi.org/10.1007/978-3-7091-9363-1_2.
K. Burgess, ed., Solid-Phase Organic Synthesis; John Wiley & Sons: New York, USA (2000).
G.J. Durant, Chem. Soc. Rev., 14, 375 (1985); https://doi.org/10.1039/cs9851400375.
A. Echavarren, A. Galan, J.M. Lehn and J. De Mendoza, J. Am. Chem. Soc., 111, 4994 (1989); https://doi.org/10.1021/ja00195a071.
O. Kamoda, K. Anzai, J. Mizoguchi, M. Shiojiri, T. Yanagi, T. Nishino and S. Kamiya, Antimicrob. Agents Chemother., 50, 3062 (2006); https://doi.org/10.1128/AAC.00036-06.
M. Bhat and S.L. Belagali, Res. Chem. Intermed., 42, 6195 (2016); https://doi.org/10.1007/s11164-016-2454-6.
M. Bhat, S.L. Belagali and D.C. Shyamala, The Natural Products J., 7, 286 (2017); https://doi.org/10.2174/2210315507666170530091940.
M. Bhat and S.L. Belagali, Anti-Infective Agents, 16, 1 (2018); https://doi.org/10.2174/2211352516666180425151720.
M. Varga, Textbook of Rabbit Medicine, Elsevier Health: UK, edn 2, pp. 137-177 (2014).
V.P. Arcangelo and A.M. Peterson, Pharmacotherapeutics for Advanced Practice: A Practical Approach, Lippincott Williams & Wilkins, vol. 536, pp 959 (2006).
M.C.S. Lourenco, M.V.N. de Souza, A.C. Pinheiro, M. de L. Ferreira, R.S.B. Gonçalves, T.C.M. Nogueira and M.A. Peralta, ARKIVOC, 181 (2007); https://doi.org/10.3998/ark.5550190.0008.f18.
M.K. Raj, C. Balachandran, V. Duraipandiyan, P. Agastian, S. Ignacimuthu and A. Vijayakumar, Med. Chem. Res., 22, 3823 (2013); https://doi.org/10.1007/s00044-012-0393-3.
M. Fathimunnisa, H. Manikandan, K. Neelakandan, N. Rajendra Prasad, S. Selvanayagam and B. Sridhar, J. Mol. Struct., 1122, 205 (2016); https://doi.org/10.1016/j.molstruc.2016.06.012.