Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Design, Synthesis, Molecular Docking and Antimicrobial Evaluation of Some Tosyl Carbamate Derivatives
Corresponding Author(s) : Mannuthusamy Gopalakrishnan
Asian Journal of Chemistry,
Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Abstract
A series of tosyl carbamates have been synthesized and screened for their antibacterial and antifungal activities. All the synthesized compounds were characterized by spectral techniques (IR, 1H, 13C NMR and mass) and elemental analysis. in silico Molecular docking method was performed to study their antimicrobial activity against the target protein 1T9U. Compound 27 showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains and compound 19 showed good antifungal activity. Molecular docking results revealed that the compound 19 exhibits minimum CDOCKER energy. Tosyl carbamate derivatives having good antimicrobial activities compared to that standard and all the synthesized compounds exhibits moderate CDOCKER scores.
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- A.L. Dopp, J.M. Miller and J.E. Tisdale, Drugs, 68, 607 (2008); https://doi.org/10.2165/00003495-200868050-00004
- M.J. Gunthorpe, C.H. Large and R. Sankar, Epilepsia, 53, 412 (2012); https://doi.org/10.1111/j.1528-1167.2011.03365.x
- J.C. Adkins and R.N. Brogden, Drugs, 55, 121 (1998); https://doi.org/10.2165/00003495-199855010-00008
- C.J. Dunn and K.L. Goa, Drugs, 61, 285 (2001); https://doi.org/10.2165/00003495-200161020-00012
- S.D. Anderson, Treat. Respir. Med., 3, 365 (2004); https://doi.org/10.2165/00151829-200403060-00004
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- T. Narasaiah and D.S. Rao, Der Pharm. Lett., 4, 854 (2012).
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- M.M. Patel and L.J. Patel, Scientific World J., 2014, 897187 (2014); https://doi.org/10.1155/2014/897187
- G. Wu, D.H. Robertson, C.L. Brooks and M. Vieth, J. Comput. Chem., 24, 1549 (2003); https://doi.org/10.1002/jcc.10306
- S. Murakami, R. Nakashima, E. Yamashita and A. Yamaguchi, Nature, 149, 587 (2002); https://doi.org/10.1038/nature01050
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- N.M.M. Hamada and N.Y.M. Abdo, Molecules, 20, 10468 (2015); https://doi.org/10.3390/molecules200610468
References
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L. Pasquato, G. Modena, L. Cotarca, P. Delogu and S. Mantovani, J. Org. Chem., 65, 8224 (2000); https://doi.org/10.1021/jo000820u
G. Raspoet, M.T. Nguyen, M. McGarraghy and A.F. Hegarty, J. Org. Chem., 63, 6878 (1998); https://doi.org/10.1021/jo9806411
A. Inesi, V. Mucciante and L. Rossi, J. Org. Chem., 63, 1337 (1998); https://doi.org/10.1021/jo971695y
F. Vacondio, C. Silva, M. Mor and B. Testa, Drug Metab. Rev., 42, 551 (2010); https://doi.org/10.3109/03602531003745960
A.L. Dopp, J.M. Miller and J.E. Tisdale, Drugs, 68, 607 (2008); https://doi.org/10.2165/00003495-200868050-00004
M.J. Gunthorpe, C.H. Large and R. Sankar, Epilepsia, 53, 412 (2012); https://doi.org/10.1111/j.1528-1167.2011.03365.x
J.C. Adkins and R.N. Brogden, Drugs, 55, 121 (1998); https://doi.org/10.2165/00003495-199855010-00008
C.J. Dunn and K.L. Goa, Drugs, 61, 285 (2001); https://doi.org/10.2165/00003495-200161020-00012
S.D. Anderson, Treat. Respir. Med., 3, 365 (2004); https://doi.org/10.2165/00151829-200403060-00004
C.M. Bonuccelli, Clin. Exp. Allergy Rev., 1, 274 (2001); https://doi.org/10.1046/j.1472-9725.2001.t01-1-00013.x
C. Fortin and V. Joly, Anti-Infect. Ther., 2, 671 (2004); https://doi.org/10.1586/14789072.2.5.671
N.Y. Rakhmanina and J.N. van den Anker, Drug Metab. Toxicol., 6, 95 (2010); https://doi.org/10.1517/17425250903483207
S.M. Clarke and F.M. Mulcahy, HIV Med., 1(Suppl. 1), 15 (2000); https://doi.org/10.1046/j.1468-1293.2000.00004.x
E. Martinez, M.A. Garcia-Viejo, J.L. Blanco, L. Bianchi, E. Buira, I. Conget, R. Casamitjana, J. Mallolas and J.M. Gatell, Clin. Infect. Dis., 31, 1266 (2000); https://doi.org/10.1086/317426
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T. Asaka, A. Manaka and H. Sugiyama, Curr. Top. Med. Chem., 3, 961 (2003); https://doi.org/10.2174/1568026033452140
K. Miller, B. Neilan and D.M.Y. Sze, Recent Pat. AntiCancer Drug Discov., 3, 14 (2003); https://doi.org/10.2174/157489208783478685
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N. Pendem, Y.R. Nelli, C. Douat, L. Fischer, M. Laguerre, E. Ennifar, B. Kauffmann and G. Guichard, Angew. Chem. Int. Ed., 52, 4147 (2013); https://doi.org/10.1002/anie.201209838
A. Scozzafava, T. Owa, A. Mastrolorenzo and C.T. Supuran, Curr. Med. Chem., 10, 925 (2003); https://doi.org/10.2174/0929867033457647
P. Deprez, J. Guillaume, R. Becker, A. Corbier, S. Didierlaurent, M. Fortin, D. Frechet, G. Hamon and B. Heckmann, J. Med. Chem., 38, 2357 (1995); https://doi.org/10.1021/jm00013a013
J.A. Campbell and D.J. Hart, J. Org. Chem., 58, 2900 (1993); https://doi.org/10.1021/jo00062a041
S. Manabe, M. Yamaguchi and Y. Ito, Chem. Commun., 49, 8332 (2013); https://doi.org/10.1039/c3cc43968b
G.M. Atkins and E.M. Burgess, J. Am. Chem. Soc., 90, 4744 (1968); https://doi.org/10.1021/ja01019a052
F. Zani and P. Vicini, Arch. Pharm., 331, 219 (1998); https://doi.org/10.1002/(SICI)1521-4184(199806)331:6<219::AIDARDP219>3.0.CO;2-U
S. Alyar and N.J. Karacan, Enzyme Inhib. Med. Chem., 24, 986 (2009); https://doi.org/10.1080/14756360802561220
F.M.A. Bar, M.A. Khanfar, A.Y. Elnagar, H. Liu, A.M. Zaghloul, F.A. Badria, P.W. Sylvester, K.F. Ahmad, K.P. Raisch and K.A. El Sayed, J. Nat. Prod., 72, 1643 (2009); https://doi.org/10.1021/np900312u
C. Hansch, P.G. Sammes and J.B. Taylor, Comprehensive Medicinal Chemistry; Pergamon Press: Oxford, vol. 2, 71 (1998).
T. Owa and T. Nagasu, Expert Opin. Ther. Pat., 10, 1725 (2000); https://doi.org/10.1517/13543776.10.11.1725
C.W. Thornber, Chem. Soc. Rev., 8, 563 (1979); https://doi.org/10.1039/cs9790800563
R.C. Ogden and C.W. Flexner, Protease Inhibitors in AIDS Therapy. Marcel Dekker: New York, USA (2001).
I. Nishimori, D. Vullo, A. Innocenti, A. Scozzafava, A. Mastrolorenzo and C.T. Supuran, Bioorg. Med. Chem. Lett., 15, 3828 (2005); https://doi.org/10.1016/j.bmcl.2005.06.055
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J.A. Picard, P.M. O’Brien, D.R. Sliskovic, M.K. Anderson, R.F. Bousley, K.L. Hamelehle, B.R. Krause and R.L. Stanfield, J. Med. Chem., 39, 1243 (1996); https://doi.org/10.1021/jm9509455
A.E. Boyd, Diabetes, 37, 847 (1988); https://doi.org/10.2337/diab.37.7.847
C.T. Supuran, A. Casini and A. Scozzafava, Med. Res. Rev., 23, 535 (2003); https://doi.org/10.1002/med.10047
T. Narasaiah and D.S. Rao, Der Pharm. Lett., 4, 854 (2012).
T. Holas, K. Vávrová, M. Síma, J. Klimentová and A. Hrabálek, Bioorg. Med. Chem., 14, 7671 (2006); https://doi.org/10.1016/j.bmc.2006.08.014
C.R. Noller and V. Baliah, J. Am. Chem. Soc., 70, 3853 (1948); https://doi.org/10.1021/ja01191a092
M.M. Patel and L.J. Patel, Scientific World J., 2014, 897187 (2014); https://doi.org/10.1155/2014/897187
G. Wu, D.H. Robertson, C.L. Brooks and M. Vieth, J. Comput. Chem., 24, 1549 (2003); https://doi.org/10.1002/jcc.10306
S. Murakami, R. Nakashima, E. Yamashita and A. Yamaguchi, Nature, 149, 587 (2002); https://doi.org/10.1038/nature01050
B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan and M. Karplus, J. Comput. Chem., 4, 187 (1983); https://doi.org/10.1002/jcc.540040211
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