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Synthesis and Antimicrobial Evaluation of Some New Thiazolo Imidazole Analogs
Corresponding Author(s) : S. Ramamurthy
Asian Journal of Chemistry,
Vol. 29 No. 12 (2017): Vol 29 Issue 12
Abstract
Thiazole and imidazole derivatives have attracted medicinal chemists owing to their extensive biological activities. Present paper describes the synthesis of some new thiazolo imidazole derivatives. 4-Substituted phenacyl bromides were prepared from substituted acetophenones. The products were condensed with thiourea to obtain 2-amino-4-(4-substituted phenyl)thiazoles which on further reaction with 4-substituted phenacyl bromides resulted in 3,6-di(substituted phenyl)imidazo[2,1-b] thiazoles (3a-3i). The formation of all the compounds was established by spectral techniques like IR, 1H NMR and Mass spectral data. The title compounds were screened for their antimicrobial activity against Gram-positive bacteria S. aureus and B. subtilis, Gram-negative bacteria E. coli and K. pneumoniae and the fungal strains like A. niger, C. albicans and C. neoformans. The results indicated that the compounds coded 3a, 3c, 3g and 3i showed significant activity than the remaining compounds.
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- B.K. Sarojini, B.G. Krishna, C.G. Darshanraj, H. Manjunatha and B.R. Bharath, Eur. J. Med. Chem., 45, 3490 (2010); https://doi.org/10.1016/j.ejmech.2010.03.039.
- G. Turan-Zitouni, S. Demirayak, A. Özdemir, Z.A. Kaplancikli and M.T. Yildiz, Eur. J. Med. Chem., 39, 267 (2004); https://doi.org/10.1016/j.ejmech.2003.11.001.
- H.I. El-Subbagh and A.M. Al-Obaid, Eur. J. Med. Chem., 31, 1017 (1996); https://doi.org/10.1016/S0223-5234(97)86181-8.
- D. Rodriguez-Lucena, F. Gaboriau, F. Rivault, I.J. Schalk, G. Lescoat and G.L.A. Mislin, Bioorg. Med. Chem., 8, 689 (2010); https://doi.org/10.1016/j.bmc.2009.11.057.
- R.G. Kalkhambkar, G.M. Kulkarni, H. Shivkumar and R.N. Rao, Eur. J. Chem., 42, 1272 (2007); https://doi.org/10.1016/j.ejmech.2007.01.023.
- B.S. Holla, K.V. Malini, B.S. Rao, B.K. Sarojini and N.S. Kumari, Eur. J. Med. Chem., 38, 313 (2003); https://doi.org/10.1016/S0223-5234(02)01447-2.
- F. Azam, I.A. Alkskas, S.L. Khokra and O. Prakash, Eur. J. Med. Chem., 44, 203 (2009); https://doi.org/10.1016/j.ejmech.2008.02.007.
- M. Himaja, K. Rai, K.V. Anish, M.V. Ramana and A.A. Karigar, J. Pharm. Scient. Innovat., 1, 67 (2012).
- D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq and J. Balzarini, Eur. J. Med. Chem., 44, 2347 (2009); https://doi.org/10.1016/j.ejmech.2008.08.010.
- D. Zampieri, M.G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone and S. Pricl, Bioorg. Med. Chem., 15, 7444 (2007); https://doi.org/10.1016/j.bmc.2007.07.023.
- C. Congiu, M.T. Cocco and V. Onnis, Bioorg. Med. Chem. Lett., 18, 989 (2008); https://doi.org/10.1016/j.bmcl.2007.12.023.
- A. Puratchikody and M. Doble, Bioorg. Med. Chem., 15, 1083 (2007); https://doi.org/10.1016/j.bmc.2006.10.025.
- F. Hadizadeh, H. Hosseinzadeh, V.S. Motamed Shariaty, M. Seifi and S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).
- F. Suzuki, T. Kuroda, Y. Nakasato, H. Manabe, K. Ohmori, S. Kitamura, S. Ichikawa and T. Ohno, J. Med. Chem., 35, 4045 (1992); https://doi.org/10.1021/jm00100a009.
- D. Olender, J. Zwawiak, V. Lukianchuk, R. Lesyk,A. Kropacz,A. Fojutowski and L. Zaprutko, Eur. J. Med. Chem., 44, 645 (2009); https://doi.org/10.1016/j.ejmech.2008.05.016.
- N.U. Güzeldemirci and Ö. Kücükbasmaci, Eur. J. Med. Chem., 45, 63 (2010); https://doi.org/10.1016/j.ejmech.2009.09.024.
- H. Ding, Z. Chen, C. Zhang, T. Xin, Y. Wang, H. Song, Y. Jiang, Y. Chen, Y. Xu and C. Tan, Molecules, 17, 4703 (2012); https://doi.org/10.3390/molecules17044703.
- J.-H. Park and C.-H. Oh, Bull. Korean Chem. Soc., 31, 2854 (2010); https://doi.org/10.5012/bkcs.2010.31.10.2854.
- A. Andreani, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi and M. Rambaldi, Eur. J. Med. Chem., 36, 743 (2001); https://doi.org/10.1016/S0223-5234(01)01266-1.
- M.B. Tehrani, S. Emami, M. Asadi, M. Saeedi, M. Mirzahekmati, S.M. Ebrahimi, M. Mahdavi, H. Nadri,A. Moradi, F.H. Moghadam, S. Farzipour, M. Vosooghi, A. Foroumadi and A. Shafiee, Eur. J. Med. Chem., 87, 759 (2014); https://doi.org/10.1016/j.ejmech.2014.10.011.
- B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, edn 5, p. 1050 (2010).
- R. Mallikarjuna Rao, G. Nagaraja Reddy and J. Sreeramulu, J. Res. Lib. Der Pharm. Chem., 3, 301(2011).
- M. Senthilraja and P. Giriraj, Int. J. Pharm. Pharm. Sci., 2, 65 (2010).
- N.C. Desai, D. Dave, M.D. Shah and G.D. Vyas, Indian. J. Chem., 39B, 277 (2000).
- J. Saravanan and S. Mohan, Asian J. Chem., 15, 67 (2003).
- S.P. Govinda and S. Mohan, Indian. J. Heterocycl. Chem., 7, 205 (1998).
References
B.K. Sarojini, B.G. Krishna, C.G. Darshanraj, H. Manjunatha and B.R. Bharath, Eur. J. Med. Chem., 45, 3490 (2010); https://doi.org/10.1016/j.ejmech.2010.03.039.
G. Turan-Zitouni, S. Demirayak, A. Özdemir, Z.A. Kaplancikli and M.T. Yildiz, Eur. J. Med. Chem., 39, 267 (2004); https://doi.org/10.1016/j.ejmech.2003.11.001.
H.I. El-Subbagh and A.M. Al-Obaid, Eur. J. Med. Chem., 31, 1017 (1996); https://doi.org/10.1016/S0223-5234(97)86181-8.
D. Rodriguez-Lucena, F. Gaboriau, F. Rivault, I.J. Schalk, G. Lescoat and G.L.A. Mislin, Bioorg. Med. Chem., 8, 689 (2010); https://doi.org/10.1016/j.bmc.2009.11.057.
R.G. Kalkhambkar, G.M. Kulkarni, H. Shivkumar and R.N. Rao, Eur. J. Chem., 42, 1272 (2007); https://doi.org/10.1016/j.ejmech.2007.01.023.
B.S. Holla, K.V. Malini, B.S. Rao, B.K. Sarojini and N.S. Kumari, Eur. J. Med. Chem., 38, 313 (2003); https://doi.org/10.1016/S0223-5234(02)01447-2.
F. Azam, I.A. Alkskas, S.L. Khokra and O. Prakash, Eur. J. Med. Chem., 44, 203 (2009); https://doi.org/10.1016/j.ejmech.2008.02.007.
M. Himaja, K. Rai, K.V. Anish, M.V. Ramana and A.A. Karigar, J. Pharm. Scient. Innovat., 1, 67 (2012).
D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq and J. Balzarini, Eur. J. Med. Chem., 44, 2347 (2009); https://doi.org/10.1016/j.ejmech.2008.08.010.
D. Zampieri, M.G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone and S. Pricl, Bioorg. Med. Chem., 15, 7444 (2007); https://doi.org/10.1016/j.bmc.2007.07.023.
C. Congiu, M.T. Cocco and V. Onnis, Bioorg. Med. Chem. Lett., 18, 989 (2008); https://doi.org/10.1016/j.bmcl.2007.12.023.
A. Puratchikody and M. Doble, Bioorg. Med. Chem., 15, 1083 (2007); https://doi.org/10.1016/j.bmc.2006.10.025.
F. Hadizadeh, H. Hosseinzadeh, V.S. Motamed Shariaty, M. Seifi and S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).
F. Suzuki, T. Kuroda, Y. Nakasato, H. Manabe, K. Ohmori, S. Kitamura, S. Ichikawa and T. Ohno, J. Med. Chem., 35, 4045 (1992); https://doi.org/10.1021/jm00100a009.
D. Olender, J. Zwawiak, V. Lukianchuk, R. Lesyk,A. Kropacz,A. Fojutowski and L. Zaprutko, Eur. J. Med. Chem., 44, 645 (2009); https://doi.org/10.1016/j.ejmech.2008.05.016.
N.U. Güzeldemirci and Ö. Kücükbasmaci, Eur. J. Med. Chem., 45, 63 (2010); https://doi.org/10.1016/j.ejmech.2009.09.024.
H. Ding, Z. Chen, C. Zhang, T. Xin, Y. Wang, H. Song, Y. Jiang, Y. Chen, Y. Xu and C. Tan, Molecules, 17, 4703 (2012); https://doi.org/10.3390/molecules17044703.
J.-H. Park and C.-H. Oh, Bull. Korean Chem. Soc., 31, 2854 (2010); https://doi.org/10.5012/bkcs.2010.31.10.2854.
A. Andreani, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi and M. Rambaldi, Eur. J. Med. Chem., 36, 743 (2001); https://doi.org/10.1016/S0223-5234(01)01266-1.
M.B. Tehrani, S. Emami, M. Asadi, M. Saeedi, M. Mirzahekmati, S.M. Ebrahimi, M. Mahdavi, H. Nadri,A. Moradi, F.H. Moghadam, S. Farzipour, M. Vosooghi, A. Foroumadi and A. Shafiee, Eur. J. Med. Chem., 87, 759 (2014); https://doi.org/10.1016/j.ejmech.2014.10.011.
B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, edn 5, p. 1050 (2010).
R. Mallikarjuna Rao, G. Nagaraja Reddy and J. Sreeramulu, J. Res. Lib. Der Pharm. Chem., 3, 301(2011).
M. Senthilraja and P. Giriraj, Int. J. Pharm. Pharm. Sci., 2, 65 (2010).
N.C. Desai, D. Dave, M.D. Shah and G.D. Vyas, Indian. J. Chem., 39B, 277 (2000).
J. Saravanan and S. Mohan, Asian J. Chem., 15, 67 (2003).
S.P. Govinda and S. Mohan, Indian. J. Heterocycl. Chem., 7, 205 (1998).