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Vol. 33 No. 5 (2021): Vol 33 Issue 5, 2021

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Microwave Assisted Synthesis of Quinoline Fused Benzodiazepines as Anxiolytic and Antimicrobial Agents

https://doi.org/10.14233/ajchem.2021.23153%20
S.B. Marganakop
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
R.R. Kamble
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
A.R. Nesaragi
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
P.K. Bayannavar
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
S.D. Joshi
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
P.P. Kattimani
Department of Studies in Chemistry, Karnatak University, Dharwad-580003, India
B.S. Sudha
Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysore-570005, India

Corresponding Author(s) : R.R. Kamble

ravichem@kud.ac.in

Asian Journal of Chemistry, Vol. 33 No. 5 (2021): Vol 33 Issue 5, 2021

Abstract

In the present study, an efficient, facile and green protocol for synthesis of quinoline fused 1,4-benzodiazepine (4a-j) by microwave irradiated condensation of 6/7/8-substituted 3-bromomethyl-2-chloro-quinoline (3a-j) obtained from 2-chloro 6/7/8-substituted quinoline-3-carbaldehyde (1a-j) with 1,2-phenylenediamine was developed. Surflex docking studies with K+ channel is one of the physiological targets and inhibition, which plays a role in the pathophysiology of depression revealed that all these compounds show consensus score in the range 2.71-3.68 indicating the summary of all forces of interaction. Further, compounds 4d, 4g and 4i exhibited potent antibacterial activity.

Keywords

Microwave assisted synthesis Quinoline Benzodiazepine Antidepressant
Marganakop, S., Kamble, R., Nesaragi, A., Bayannavar, P., Joshi, S., Kattimani, P., & Sudha, B. (2021). Microwave Assisted Synthesis of Quinoline Fused Benzodiazepines as Anxiolytic and Antimicrobial Agents. Asian Journal of Chemistry, 33(5), 1107–1114. https://doi.org/10.14233/ajchem.2021.23153
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References
  1. J.-H. Choi, J.-E. Kim and B.-K. Kaang, Mol. Brain, 3, 1 (2010); https://doi.org/10.1186/1756-6606-3-1
  2. R. Dua, S. Shrivastava, S.K. Sonwane and S.K. Srivastava, Adv. Biol. Res., 5, 120 (2011).
  3. D.J. Newman, G.M. Cragg and K.M. Snader, J. Nat. Prod., 66, 1022 (2003); https://doi.org/10.1021/np030096l
  4. Y.-L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu and C.-C. Tzeng, J. Med.Chem., 44, 2374 (2001); https://doi.org/10.1021/jm0100335
  5. L.Y. Vargas M, M.V. Castelli, V.V. Kouznetsov, J.M. Urbina G, S.N. López, M. Sortino, R.D. Enriz, J.C. Ribas and S. Zacchino, Bioorg. Med. Chem., 11, 1531 (2003); https://doi.org/10.1016/S0968-0896(02)00605-3
  6. K.C. Fang, Y.L. Chen, J.Y. Sheu, T.C. Wang and C.C. Tzeng, J. Med. Chem., 43, 3809 (2000); https://doi.org/10.1021/jm000153x
  7. L. Dassonneville, K. Bonjean, M.-C. De Pauw-Gillet, P. Colson, C. Houssier, J. Quetin-Leclercq, L. Angenot and C. Bailly, Biochemistry, 38, 7719 (1999); https://doi.org/10.1021/bi990094t
  8. B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006); https://doi.org/10.1016/j.bmc.2005.10.053
  9. R.I. Fryer, eds.: E.C. Taylor, Bicyclic Diazepines. In Comprehensive Heterocyclic Chemistry, Wiley: New York, Chapter II, p. 50 (1991).
  10. K. Sorra, S.C. Chen, C.F. Chang, S. Pusuluri, K. Mukkanti, C.R. Wu and T.H. Chuang, Int. J. Mol. Sci., 15, 16500 (2014); https://doi.org/10.3390/ijms150916500
  11. M.D. Kelly, A. Smith, G. Banks, P. Wingrove, P.W. Whiting, J. Atack, G.R. Seabrook and K.A. Maubach, Br. J. Pharm., 135, 248 (2002); https://doi.org/10.1038/sj.bjp.0704459
  12. O. Meth-Cohn and B. Tarnowski, Tetrahedron Lett., 21, 3721 (1980); https://doi.org/10.1016/S0040-4039(00)78756-9
  13. T. Tilakraj and S.Y. Ambekar, J. Indian Chem. Soc., 62, 251 (1985).
  14. Z. Cziaky and Z. Szabo, J. Heterocycl. Chem., 32, 755 (1995); https://doi.org/10.1002/jhet.5570320311
  15. K.R. Rao, N. Bhanumathi and P.B. Sattur, J. Heterocycl. Chem., 28, 1339 (1991); https://doi.org/10.1002/jhet.5570280527
  16. P.B. Sattur, N. Bhanumathi and K.R. Rao, Heterocycles, 24, 1683 (1986); https://doi.org/10.3987/R-1986-06-1683
  17. J.M. Bakke and J. Riha, J. Heterocycl. Chem., 38, 99 (2001); https://doi.org/10.1002/jhet.5570380114
  18. B. Elisabet, L. Enric, V. Miquel and D.P. Maria, eds.: V. Janka, 1,4- Benzodiazepines and New Derivatives, Intech Open Ltd, London, p. 63 (2018).
  19. S.Y. Jeong, T.S. Ha, C.S. Park, D.Y. Uhm and S. Chung, Mol. Cells, 12, 97 (2001).
  20. J.H. Shin, S. Chung, E.J. Park, D.Y. Uhm and C.K. Suh, FEBS Letter, 415, 299 (1997); https://doi.org/10.1016/S0014-5793(97)01144-7
  21. M.P. Kaster, P.K. Ferreira, A.R.S. Santos and A.L.S. Rodrigues, Behav.Brain Res., 165, 204 (2005); https://doi.org/10.1016/j.bbr.2005.06.031
  22. D.A. Doyle, J. Morais Cabral, R.A. Pfuetzner, A. Kuo, J.M. Gulbis, S.L. Cohen, B.T. Chait and R. Mackinnon, Science, 280, 69 (1998); https://doi.org/10.1126/science.280.5360.69
  23. O. Meth-Cohn, B. Narine and B. Tarnowski, J. Chem. Soc. Perkin Trans. I, 1520 (1981); https://doi.org/10.1039/p19810001520
  24. O. Meth-Cohn, B. Narine, A. Tarnowski, R. Hayes, A. Keyzad, S. Rhouati and A. Robinson, J. Chem. Soc. Perkin Trans. I, 2509 (1981); https://doi.org/10.1039/p19810002509
  25. S.K. Shaikh, R.R. Kamble, S.M. Somagond, H.C. Devarajegowda, S.R. Dixit and S.D. Joshi, Eur. J. Med. Chem., 128, 258 (2017); https://doi.org/10.1016/j.ejmech.2017.01.043
  26. J.H. Rigby and D.M. Danca, Tetrahedron Lett., 38, 4969 (1997); https://doi.org/10.1016/S0040-4039(97)01077-0
  27. J. Gasteiger and M. Marsili, Tetrahedron, 36, 3219 (1980); https://doi.org/10.1016/0040-4020(80)80168-2
  28. P.G. Mandhane, R.S. Joshi, P.S. Mahajan, M.D. Nikam, D.R. Nagargoje and C.H. Gill, Arab. J. Chem., 8, 474 (2015); https://doi.org/10.1016/j.arabjc.2011.01.025
  29. P.P. Kattimani, R.R. Kamble and G.Y. Meti, RSC Adv., 5, 29447 (2015); https://doi.org/10.1039/C5RA00021A
  30. C.A. Lipinski, F. Lombardo, B.W. Dominy and P.J. Feeney, Adv. Drug Deliv. Rev., 46, 3 (2001); https://doi.org/10.1016/S0169-409X(00)00129-0
  31. J.P. Stewart, J. Comput. Chem., 10, 209 (1989); https://doi.org/10.1002/jcc.540100208
  32. I.D. Kuntz, J.M. Blaney, S.J. Oatley, R. Langridge and T.E. Ferrin, J. Mol. Biol., 161, 269 (1982); https://doi.org/10.1016/0022-2836(82)90153-X
  33. I. Muegge and Y.C. Martin, J. Med. Chem., 42, 791 (1999); https://doi.org/10.1021/jm980536j
  34. G. Jones, P. Willett, R. Glen, A.R. Leach and R. Taylor, J. Mol. Biol., 267, 727 (1997); https://doi.org/10.1006/jmbi.1996.0897
  35. M.D. Eldridge, C.W. Murray, T.R. Auton, G.V. Paolini and R.P. Mee, J. Comput. Aided Mol. Des., 11, 425 (1997); https://doi.org/10.1023/A:1007996124545
  36. R. Schwalve, L.S. Moore and A.C. Goodwin, Antimicrobial Susceptibility Testing Protocols, CRC Press, Taylor and Francis Group: Boca Raton, pp 75-80 (2007).
  37. M. Basanagouda, K. Shivashankar, M.V. Kulkarni, V.P. Rasal, H. Patel, S.S. Mutha and A.A. Mohite, Eur. J. Med. Chem., 45, 1151 (2010); https://doi.org/10.1016/j.ejmech.2009.12.022
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