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This work is licensed under a Creative Commons Attribution 4.0 International License.
Green Synthesis Approaches of 2-Bromo-4-methyl thiazole-5-carboxamide Derivatives as Potent Microbial Agents
Corresponding Author(s) : Satyanarayana Battu
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
As a part of our ongoing research in the development of new, selective and environmental friendly methodologies, herein we report a new series of 2-bromo-4-methylthiazole-5-carboxamide derivatives using polyethylene glycol-400 (PEG-400) as a solvent. All the newly synthesized compounds were screened to their in vitro antimicrobial activities and all the compounds exhibited remarkable growth inhibition of wide spectrum of Gram-positive bacteria and Gram-negative bacteria. Molecular docking was done performed computational software GOLD (Genetic algorithm based, flexible ligand, partial flexibility for protein).
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- J. Quiroga, P. Hernandez, B. Insuasty, R. Abonia, J. Cobo, A. Sanchez, M. Nogueras and J.N. Low, J. Chem. Soc., Perkin Trans. 1, 4, 555 (2002); https://doi.org/10.1039/b109676a.
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References
J. Quiroga, P. Hernandez, B. Insuasty, R. Abonia, J. Cobo, A. Sanchez, M. Nogueras and J.N. Low, J. Chem. Soc., Perkin Trans. 1, 4, 555 (2002); https://doi.org/10.1039/b109676a.
I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Westwell and M.F.G. Stevens, J. Med. Chem., 45, 744 (2002); https://doi.org/10.1021/jm011025r.
M.T. Chhabria, S. Patel, P. Modi and P.S. Brahmkshatriya, Curr. Top. Med. Chem., 16, 2841 (2016); https://doi.org/10.2174/1568026616666160506130731.
A.R. Ali, E.R. El-Bendary, M.A. Ghaly and I.A. Shehata, Eur. J. Med. Chem., 75, 492 (2014); https://doi.org/10.1016/j.ejmech.2013.12.010.
L. Bettendorff, F. Mastrogiacomo, S.J. Kish and T. Grisar, J. Neurochem., 66, 250 (1996); https://doi.org/10.1046/j.1471-4159.1996.66010250.x.
Y. Yamada, N. Seki, T. Kitahara, M. Takahashi and M. Matsui, Agric. Bio. Chem., 34, 780 (1970).
E.H. White, F. McCapra, G.F. Field and W.D. McElroy, J. Am. Chem. Soc., 83, 2402 (1961); https://doi.org/10.1021/ja01471a051.
K.D. Hargrave, F.K. Hess and J.T. Oliver, J. Med. Chem., 26, 1158 (1983); https://doi.org/10.1021/jm00362a014.
P. Karegoudar, M.S. Karthikeyan, D.J. Prasad, M. Mahalinga, B.S. Holla and N.S. Kumari, Eur. J. Med. Chem., 43, 261 (2008); https://doi.org/10.1016/j.ejmech.2007.03.014.
N. Masuda, O. Yamamoto, M. Fujii, T. Ohgami, A. Moritomo, T. Kontani, S. Kageyama and M. Ohta, Synth. Commun., 35, 2305 (2005); https://doi.org/10.1080/00397910500186730.
D. González Cabrera, F. Douelle, T.-S. Feng, A.T. Nchinda, Y. Younis, K.L. White, Q. Wu, E. Ryan, J.N. Burrows, D. Waterson, M.J. Witty, S. Wittlin, S.A. Charman and K. Chibale, J. Med. Chem., 54, 7713 (2011); https://doi.org/10.1021/jm201108k.
W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G.J. Taylor, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko, I. Sircar and B.A. Steinbaugh, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.
R.N. Sharma, F.P. Xavier, K.K. Vasu, S.C. Chaturvedi and S.S. Pancholi, J. Enzyme Inhib. Med. Chem., 24, 890 (2009); https://doi.org/10.1080/14756360802519558.
J J.C. Jaen, L.D. Wise, B.W. Caprathe, H. Tecle, S. Bergmeier, C.C. Humblet, T.G. Heffner, L.T. Meltzer and T.A. Pugsley, J. Med. Chem., 33, 311 (1990); https://doi.org/10.1021/jm00163a051.
V. Ravichandran, B.R. Prashantha Kumar, S. Sankar and R.K. Agrawal, Eur. J. Med. Chem., 44, 1180 (2009); https://doi.org/10.1016/j.ejmech.2008.05.036.
N. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey and E. Kendi, Arch. Pharm. Pharm. Med. Chem., 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AIDARDP343>3.0.CO;2-0.
J.S. Carter, S. Kramer, J.J. Talley, T. Penning, P. Collins, M.J. Graneto, K. Seibert, C. Koboldt, J. Masferrer and B. Zweifel, Bioorg. Med. Chem. Lett., 9, 1171 (1999); https://doi.org/10.1016/S0960-894X(99)00157-2.
A. Badorc, M.F. Bordes, P. De Cointet, P. Savi, A. Bernat, A. Lale, M. Petitou, J.P. Maffrand and J.M. Herbert, J. Med. Chem., 40, 3393 (1997); https://doi.org/10.1021/jm970240y.
J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen and F.U. Geschke, J. Med. Chem., 44, 619 (2001); https://doi.org/10.1021/jm0010623.
T.-B. Wei and Y.-M. Zhang, Synth. Commun., 29, 2943 (1999); https://doi.org/10.1080/00397919908086466.
J. Chen, S.K. Spear, J.G. Huddleston and R.D. Rogers, Green Chem., 7, 64 (2005); https://doi.org/10.1039/b413546f.
S. Chandrasekhar, C. Narsihmulu, S.S. Sultana and N.R. Reddy, Org. Lett., 4, 4399 (2002); https://doi.org/10.1021/ol0266976.
K.S. Kim, S.D. Kimball, R.N. Misra, D.B. Rawlins, J.T. Hunt, H.-Y. Xiao, S. Lu, L. Qian, W.-C. Han, W. Shan, T. Mitt, Z.-W. Cai, M.A. Poss, H. Zhu, J.S. Sack, J.S. Tokarski, C.Y. Chang, N. Pavletich, A. Kamath, W.G. Humphreys, P. Marathe, I. Bursuker, K.A. Kellar, U. Roongta, R. Batorsky, J.G. Mulheron, D. Bol, C.R. Fairchild, F.Y. Lee and K.R. Webster, J. Med. Chem., 45, 3905 (2002); https://doi.org/10.1021/jm0201520.
E. Valeur and M. Bradley, Chem. Soc. Rev., 38, 606 (2009); https://doi.org/10.1039/B701677H.
I.M. Kompis, K. Islam and R.L. Then, Chem. Rev., 105, 593 (2005); https://doi.org/10.1021/cr0301144.