Catalyst Free and Energy Economical Synthesis of Thiazole Derivatives Bearing Azo Imine Linkage with Imidazole as Antimicrobial Agents

Several strategies have been reported for the synthesis of thiazole derivatives.However, many of these methods suffer from several drawbacks. Several modifications have been made to counter these problems. Here, we have synthesized a new series of 2-(2-((1HImidazol- 4-yl)methylene)hydrazinyl)-4-(4-substitutedphenyl)thiazoles without using the catalyst at room temperature.The structures of synthesized compounds have been confirmed by spectral analysis, such as Mass, IR, 1H NMR and 13C NMR. All synthesized compounds were screened for in vitro antibacterial activity against some gram-positive and gram-negative bacteria.The thiazole derivatives, with a pharmacologically potent group, discussed in this article may provide valued therapeutic important in the treatment of microbial diseases, especially against bacterial and fungal infections.

[1]  V. Kant,et al.  A Review on Biological Activity of Imidazole and Thiazole Moieties and their Derivatives , 2013 .

[2]  N. Desai,et al.  Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles , 2013, European Journal of Medicinal Chemistry.

[3]  V. Alagarsamy,et al.  Synthesis of Novel Thiazole Derivatives as Analgesic Agents , 2011 .

[4]  A. Idhayadhulla,et al.  Synthesis, Characterization and Antimicrobial Activity of New Pyrrole Derivatives , 2011 .

[5]  G. SenthilKumar,et al.  Thiazole: A Valuable Insight into Recent Advances, Synthesis and Biological Activities , 2011 .

[6]  D. Shinde,et al.  Synthesis and hypolipidemic activity of novel 2-(4-(2-substituted aminothiazole-4-yl) phenoxy) acetic acid derivatives. , 2010, European journal of medicinal chemistry.

[7]  A. K. Prajapati,et al.  SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME SUBSTITUTED AMINO THIAZOLE DERIVATIVES , 2010 .

[8]  K. Parmar,et al.  Synthesis and Antibacterial Evaluation of Some Novel 2-Arylamino-4-phenyl-thiazolyl Derivatives , 2010 .

[9]  N. Siddiqui,et al.  Triazole incorporated thiazoles as a new class of anticonvulsants: design, synthesis and in vivo screening. , 2010, European journal of medicinal chemistry.

[10]  C. Müller,et al.  2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. , 2010, Bioorganic & medicinal chemistry.

[11]  M. Hata,et al.  Discovery and in vitro and in vivo profiles of 4-fluoro-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide as novel class of an orally active metabotropic glutamate receptor 1 (mGluR1) antagonist. , 2009, Bioorganic & medicinal chemistry letters.

[12]  Walid Fathalla.  Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds , 2008 .

[13]  S. Tala,et al.  Synthesis of Some New Pyrazolo[3,4-d]pyrimidines and Thiazolo [4,5-d]pyrimidines and Evaluation of Their Antimicrobial Activities , 2008 .

[14]  H. Joshi,et al.  Synthesis and antimicrobial activity of some new pyrazolo[3,4-d]pyrimidines and thiazolo[4,5-d]pyrimidines , 2008 .

[15]  T. M. Potewar,et al.  Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: a practical approach towards the synthesis of Fanetizole , 2007 .

[16]  M. P. Kaushik,et al.  An efficient method for the synthesis of 2-aminothiazoles using silica chloride as a heterogeneous catalyst , 2007 .

[17]  P. Sánchez-Andrada,et al.  On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes. , 2006, The Journal of organic chemistry.

[18]  B. Das,et al.  A rapid and high-yielding synthesis of thiazoles and aminothiazoles using ammonium-12-molybdophosphate , 2006 .

[19]  G. Mena-Rejón,et al.  Preparation, antimicrobial activity, and toxicity of 2‐amino‐4‐arylthiazole derivatives , 2006 .

[20]  E. McDonald,et al.  Facile generation of a library of 5-aryl-2-arylsulfonyl-1,3-thiazoles , 2006 .

[21]  K. R. Rao,et al.  Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin , 2005 .

[22]  K. Roy,et al.  Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists using FA and GFA techniques. , 2005, Bioorganic & medicinal chemistry.

[23]  P. la Colla,et al.  Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. , 2003, Bioorganic & medicinal chemistry.

[24]  D. Hadjipavlou-Litina,et al.  Synthesis and Biological Evaluation of New 4,5-Disubstituted-Thiazolyl Amides, Derivatives of 4-Hydroxy-Piperidine or of 4-N-Methyl Piperazine , 2003, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[25]  B. S. Holla,et al.  Synthesis of some new 2,4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents. , 2003, European journal of medicinal chemistry.

[26]  J. N. Low,et al.  Control of the reaction between 2-aminobenzothiazoles and Mannich bases. Synthesis of pyrido[2,1-b][1,3]benzothiazoles versus [1,3]benzothiazolo[2,3-b]quinazolines , 2002 .

[27]  M. Stevens,et al.  Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs. , 2002, Journal of medicinal chemistry.

[28]  J. Rudolph,et al.  seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties. , 2001, Journal of medicinal chemistry.

[29]  J. R. Porter,et al.  A Convenient Microdilution Method for Screening Natural Products Against Bacteria and Fungi , 2001 .

[30]  G. Çapan,et al.  Synthesis and Hypnotic Activity of New 4‐Thiazolidinone and 2‐Thioxo‐4,5‐imidazolidinedione Derivatives , 1999, Archiv der Pharmazie.

[31]  C. Koboldt,et al.  Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors. , 1999, Bioorganic & medicinal chemistry letters.

[32]  J. Herbert,et al.  New orally active non-peptide fibrinogen receptor (GpIIb-IIIa) antagonists: identification of ethyl 3-[N-[4-[4-[amino[(ethoxycarbonyl) imino]methyl]phenyl]-1,3-thiazol-2-yl]-N-[1-[(ethoxycarbonyl)methyl]pip erid -4-yl]amino]propionate (SR 121787) as a potent and long-acting antithrombotic agent. , 1997, Journal of medicinal chemistry.

[33]  A. Tsuruoka,et al.  Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. , 1997, Chemical & pharmaceutical bulletin.

[34]  J M Morin,et al.  Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. , 1995, Journal of medicinal chemistry.

[35]  P J Sanfilippo,et al.  Novel thiazole based heterocycles as inhibitors of LFA-1/ICAM-1 mediated cell adhesion. , 1995, Journal of medicinal chemistry.

[36]  H. Ishikawa,et al.  Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7 , 1994 .

[37]  A. Doherty,et al.  Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. , 1992, Journal of medicinal chemistry.

[38]  T. Heffner,et al.  4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. , 1990, Journal of medicinal chemistry.

[39]  K. D. Hargrave,et al.  N-(4-substituted-thiazolyl)oxamic acid derivatives, a new series of potent, orally active antiallergy agents. , 1983, Journal of medicinal chemistry.

[40]  Ronald Breslow,et al.  On the Mechanism of Thiamine Action. IV.1 Evidence from Studies on Model Systems , 1958 .

[41]  R. J. Fosbinder,et al.  Sulfanilamido Derivatives of Heterocyclic Amines , 1939 .