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Abstract
In the present paper, the syntheses of some new thiazoles incorporated with pyran moiety using α-bromo ketones and α,α-dibromo ketone are reported and found that both α-bromo ketones and α,α-dibromo ketone are synthetically equivalent. All the new compounds were characterized by spectral and analytical data. In vitro antibacterial activity shows that some of compounds are more potent than standard drugs against specific bacterial strains. All the compounds show fair antifungal activity, however, none of the compounds is more potent than the standard drug.
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References
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References
O. Kouatly, A. Geronikaki, C. Kamoutsis, D. Hadjipavlou-Litina and P. Eleftheriou, Eur. J. Med. Chem., 44, 1198 (2009); https://doi.org/10.1016/j.ejmech.2008.05.029.
R.S. Giri, H.M. Thaker, T. Giordano, J. Williams, D. Rogers, V. Sudersanam and K.K. Vasu, Eur. J. Med. Chem., 44, 2184 (2009); https://doi.org/10.1016/j.ejmech.2008.10.031.
K. Liaras, A. Geronikaki, J. Glamoclija, A. Ciric and M. Sokovic, Bioorg. Med. Chem., 19, 3135 (2011); https://doi.org/10.1016/j.bmc.2011.04.007.
A.A. Chavan and N.R. Pai, ARKIVOC, 148 (2007); https://doi.org/10.3998/ark.5550190.0008.g16.
J.S. Barradas, M.I. Errea, N.B. D’Accorso, C.S. Sepúlveda and E.B. Damonte, Eur. J. Med. Chem., 46, 259 (2011); https://doi.org/10.1016/j.ejmech.2010.11.012.
S.A.F. Rostom, Bioorg. Med. Chem., 14, 6475 (2006); https://doi.org/10.1016/j.bmc.2006.06.020.
A. Padmaja, C. Rajasekhar, A. Muralikrishna and V. Padmavathi, Eur. J. Med. Chem., 46, 5034 (2011); https://doi.org/10.1016/j.ejmech.2011.08.010.
J.B. Sperry and D.L. Wright, Curr. Opin. Drug Discov. Devel., 8, 723 (2005).
M. Zia-ur-Rehman, J.A. Choudary and S. Ahmad, Bull. Korean Chem. Soc., 26, 1771 (2005); https://doi.org/10.5012/bkcs.2005.26.11.1771.
N. Suzuki, Y. Tanaka and R. Dohmori, Chem. Pharm. Bull. (Tokyo), 28, 235 (1980); https://doi.org/10.1248/cpb.28.235.
G.W.A. Milne, Ashgate Handbook of Antineoplastic Agents, Ashgate Publishing Ltd., UK (2000).
(a) H. Zhao, Drug Discov. Today, 12, 149 (2007); https://doi.org/10.1016/j.drudis.2006.12.003. (b) G. Schneider, P. Schneider and S. Renner, QSAR Comb. Sci., 25, 1162 (2006); https://doi.org/10.1002/qsar.200610091. (c) H.-J. Böhm, A. Flohr and M. Stahl, Drug Discov. Today. Technol., 1, 217 (2004); https://doi.org/10.1016/j.ddtec.2004.10.009.
(a) E. Biron, J. Chatterjee and H. Kessler, Org. Lett., 8, 2417 (2006); https://doi.org/10.1021/ol0607645. (b) S. Deng and J. Taunton, Org. Lett., 7, 299 (2005); https://doi.org/10.1021/ol047660j.
R.E. Dolle, B. Le Bourdonnec, G.A. Morales, K.J. Moriarty and J.M. Salvino, J. Comb. Chem., 8, 597 (2006); https://doi.org/10.1021/cc060095m.
V.K. Ahluwalia, B. Mehta and M. Rawat, Synth. Commun., 22, 2697 (1992); https://doi.org/10.1080/00397919208021670.
V.K. Ahluwalia, K.K. Arora, G. Kaur and B. Mehta, Synth. Commun., 17, 333 (1987); https://doi.org/10.1080/00397918708077314.
V.K. Ahluwalia, B. Mehta and R. Kumar, Synth. Commun., 19, 619 (1989); https://doi.org/10.1080/00397918908050707.
S.P. Singh, D. Kumar, H. Batra, R. Naithani, I. Rozas and J. Elguero, Can. J. Chem., 78, 1109 (2000); https://doi.org/10.1139/v00-104.
O.M. Prakash, A. Kumar, A. Sadana and S.P. Singh, Synth. Commun., 32, 2663 (2002); https://doi.org/10.1081/SCC-120006030.
A. Kumar, O. Prakash, M. Kinger and S.P. Singh, Can. J. Chem., 84, 438 (2006); https://doi.org/10.1139/v06-015.
J. Elguero, A. Martíanez, S.P. Singh, M. Grover and L.S. Tarar, J. Heterocycl. Chem., 27, 865 (1990); https://doi.org/10.1002/jhet.5570270409.
(a) D. Kumar and S.P. Singh, J. Indian Chem. Soc., 83, 419 (2006). (b) O. Prakash, A. Kumar and S.P. Singh, Heterocycles, 63, 1193 (2004); https://doi.org/10.3987/REV-03-572. (c) M. Moreno-Mañas and R. Pleixats, Adv. Heterocycl. Chem., 53, 1 (1992); https://doi.org/10.1016/S0065-2725(08)60861-2.
O. Prakash, D.K. Aneja, K. Hussain, P. Lohan, P. Ranjan, S. Arora, C. Sharma and K.R. Aneja, Eur. J. Med. Chem., 46, 5065 (2011); https://doi.org/10.1016/j.ejmech.2011.08.019.
A. Kumar, R. Prakash and S.P. Singh, Synth. Commun., 35, 461 (2005); https://doi.org/10.1081/SCC-200048970.
T.M. Harris, C.M. Harris and C.K. Brush, J. Org. Chem., 35, 1329 (1970); https://doi.org/10.1021/jo00830a016.
S. Paul, V. Gupta, R. Gupta and A. Loupy, Tetrahedron Lett., 44, 439 (2003); https://doi.org/10.1016/S0040-4039(02)02601-1.