One-Pot Synthesis of Thiazoles via Hantzsch Thiazole Reaction and Their Antimicrobial Activity

Prabhunath Yogi; Mohammad Ashid; Nasir Hussain; Saba Khan; Ajit Joshi

doi:10.14233/ajchem.2016.19603

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

Issue Published : December 30, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

One-Pot Synthesis of Thiazoles via Hantzsch Thiazole Reaction and Their Antimicrobial Activity

https://doi.org/10.14233/ajchem.2016.19603

Prabhunath Yogi

Organic Chemistry Laboratory, Department of Chemistry, Mewar University, Gangrar-312 901, India

Mohammad Ashid

Organic Chemistry Laboratory, Department of Chemistry, Mewar University, Gangrar-312 901, India

Nasir Hussain

Organic Chemistry Laboratory, Vidya Bhawan Rural Institute, Udaipur-313 011, India

Saba Khan

Organic Chemistry Laboratory, Vidya Bhawan Rural Institute, Udaipur-313 011, India

Ajit Joshi

Organic Chemistry Laboratory, Department of Chemistry, Mewar University, Gangrar-312 901, India

Corresponding Author(s) : Prabhunath Yogi

prabhunath1987@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 4 (2016): Vol 28 Issue 4
Article Published : December 30, 2015

Abstract

In this work, substituted 2-bromo-1-phenylethanone compounds (1a-c) synthesized by reaction of bromine and various subtituted acetophenone. Compounds (1a-c) treated with thiosemicarbazide and several carbonyl species to gave corresponding substituted 4-phenyl-1,3-thiazole derivatives (2a-c to 6a-c) via multicomponent reaction and Hantzsch thiazole synthesis. All the synthesized compound tested for their antimicrobial activity.

Keywords

Hantzsch thiazole synthesis Pyrazolone Thiazolidione Isatine

Yogi, P., Ashid, M., Hussain, N., Khan, S., & Joshi, A. (2015). One-Pot Synthesis of Thiazoles via Hantzsch Thiazole Reaction and Their Antimicrobial Activity. Asian Journal of Chemistry, 28(4), 927–932. https://doi.org/10.14233/ajchem.2016.19603

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References

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References

K.R.A. Abdellatif, M.A. Abdelgawad, H.A.H. Elshemy and S.S.R. Alsayed, Bioorg. Chem., 64, 1 (2016); doi:10.1016/j.bioorg.2015.11.001.

V.B. Jadhav, M.V. Kulkarni, V.P. Rasal, S.S. Biradar and M.D. Vinay, J. Med. Chem., 43, 1721 (2008); doi:10.1016/j.ejmech.2007.06.023.

R. Budriesi, P. Ioan, A. Locatelli, S. Cosconati, A. Leoni, M.P. Ugenti, A. Andreani, R. Di Toro, A. Bedini, S. Spampinato, L. Marinelli, E. Novellino and A. Chiarini, J. Med. Chem., 51, 1592 (2008); doi:10.1021/jm070681+.

K.F.M. Atta, O.O.M. Farahat, A.Z.A. Ahmed and M.G. Marei, Molecules, 16, 5496 (2011); doi:10.3390/molecules16075496.

T. Juspin, M. Laget, T. Terme, N. Azas and P. Vanelle, Eur. J. Med. Chem., 45, 840 (2010); doi:10.1016/j.ejmech.2009.10.048.

R. Budriesi, P. Ioan, A. Leoni, N. Pedemonte, A. Locatelli, M. Micucci, A. Chiarini and L.J.V. Galietta, J. Med. Chem., 54, 3885 (2011); doi:10.1021/jm200199r.

B.C.C. Cantello, M.A. Cawthorne, G.P. Cottam, P.T. Duff, D. Haigh, R.M. Hindley, C.A. Lister, S.A. Smith and P.L. Thurlby, Med. Chem., 37, 3977 (1994); doi:10.1021/jm00049a017.

A. Chimirri, S. Grasso, C. Molica, A.M. Monforte, P. Monforte, M. Zappala, G. Bruno, F. Nicolo, M. Witvrouw, H. Jonckeere, J. Balzarini and E. De Clercq, Antivir. Chem. Chemother., 8, 363 (1997); doi:10.1177/095632029700800409.

B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, edn 5, p. 807 (1989).

J.M. Lehmann, L.B. Moore, T.A. Smith-Oliver, W.O. Wilkison, T.M. Willson and S.A. Kliewer, J. Biol. Chem., 270, 12953 (1995); doi:10.1074/jbc.270.22.12953.

U. Sehlstedt, P. Aich, J. Bergman, H. Vallberg, B. Nordén and A. Gräslund, J. Mol. Biol., 278, 31 (1998); doi:10.1006/jmbi.1998.1670.

A. Jeney, Bioorg. Med. Chem., 177, 220 (1960).

J.M. Grisar, F.N. Bolkenius, M.A. Petty and J. Verne, J. Med. Chem., 38, 453 (1995); doi:10.1021/jm00003a008.

B. Jójárt, T.A. Martinek and Á. Márki, J. Comput. Aided Mol. Des., 19, 341 (2005); doi:10.1007/s10822-005-7137-0.

S.S. Sangapure and R. Basawaraj, Indian J. Pharm. Sci., 66, 221 (2004).

M. Ono, M.P. Kung, C. Hou and H.F. Kung, Nucl. Med. Biol., 29, 633 (2002); doi:10.1016/S0969-8051(02)00326-8.

W.M. Luo, Q.S. Yu, M. Zhan, D. Parrish, J.R. Deschamps, S.S. Kulkarni, H.W. Holloway, G.M. Alley, D.K. Lahiri, A. Brossi and N.H. Greig, J. Med. Chem., 48, 986 (2005); doi:10.1021/jm049309+.

M. Cowart, R. Faghih, M.P. Curtis, G.A. Gfesser, Y.L. Bennani, L.A. Black, L. Pan, K.C. Marsh, J.P. Sullivan, T.A. Esbenshade, G.B. Fox and A.A. Hancock, J. Med. Chem., 48, 38 (2005); doi:10.1021/jm040118g.

A.F. Abdel-Magid, B.E. Maryanoff, S.J. Mehrman, M.H. Parker and A.B. Reitz, US Patent 276,528 (2006).

M.E. Page, J.F. Cryan, A. Sullivan, A. Dalvi, B. Saucy, D.R. Manning and I. Lucki, J. Pharmacol. Exp. Ther., 302, 1220 (2002); doi:10.1124/jpet.102.034280.

I. Hayakawa, R. Shioya, T. Agatsuma, H. Furukawa, S. Naruto and Y. Sugano, Bioorg. Med. Lett., 14, 4383 (2004); doi:10.1016/j.bmcl.2004.06.067.

M.R. Saberi, T.K. Vinh, S.W. Yee, B.J.N. Griffiths, P.J. Evans and C. Simons, J. Med. Chem., 49, 1016 (2006); doi:10.1021/jm0508282.

S.K. Lee, B. Cui, R.P. Mehta, A.D. Kinghorn and J.M. Pezzuto, Chem. Biol. Interact., 115, 215 (1998); doi:10.1016/S0009-2797(98)00073-8.

S. Pautus, S.W. Yee, M. Jayne, M.P. Coogan and C. Simons, Bioorg. Med. Chem., 14, 3643 (2006); doi:10.1016/j.bmc.2006.01.018.

R.H. Udupi, A.S. Kushnoor and A.R. Bhat, Indian J. Heterocycl. Chem., 8, 63 (1998).

S.S. Korgaokar, P.H. Patil, M.J. Shah and H.H. Parekh, Indian J. Pharm. Sci., 58, 222 (1996).

O.O. Ajani, C.A. Obafemi, C.O. Ikpo, K.O. Ogunniran and O.C. Nwinyi, Chem. Heterocycl. Comp., 45, 1370 (2009); doi:10.1007/s10593-010-0435-z.

D. Nauduri and G.B. Reddy, Chem. Pharm. Bull. (Tokyo), 46, 1254 (1998); doi:10.1248/cpb.46.1254.

E. Palaska, M.I. Aytemir, T. Uzbay and D. Erol, Eur. J. Med. Chem., 36, 539 (2001); doi:10.1016/S0223-5234(01)01243-0.

O. Ruhogluo, Z. Ozdemir, U. Calis, B. Gumusel and A.A. Bilgin, Arzneimittelforschung Drug. Res., 55, 431 (2005); doi:10.1055/s-0031-1296884.

Y. Rajendra Prasad, A. Lakshmana Rao, L. Prasoona, K. Murali and P. Ravi Kumar, Bioorg. Med. Chem. Lett., 15, 5030 (2005); doi:10.1016/j.bmcl.2005.08.040.

Z. Özdemir, H.B. Kandilci, B. Gümüsel, Ü. Çalis and A.A. Bilgin, Eur. J. Med. Chem., 42, 373 (2007); doi:10.1016/j.ejmech.2006.09.006.

E.C. Taylor and H.H. Patel, Tetrahedron, 48, 8089 (1992); doi:10.1016/S0040-4020(01)80479-8.

A.A. Santilli, D.H. Kim and F.J. Gregory, J. Pharm. Sci., 64, 1057 (1975); doi:10.1002/jps.2600640646.

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

One-Pot Synthesis of Thiazoles via Hantzsch Thiazole Reaction and Their Antimicrobial Activity

Corresponding Author(s) : Prabhunath Yogi

Abstract

Keywords

Full Article

Download Citation

References

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