Synthesis of functionalized dihydroimidazo[1,2-A]pyridines and 4-thiazolidinone derivatives from maleimide, as new class of antimicrobial agents

Abstract New dihydroimidazo[1,2-a]pyridines and 4-thiazolidinone derivatives have been synthesized by condensation reaction of substituted maleimide with 2,3-diaminopyridine or thiosemicarbazone under neutral or acidic medium in low and good yields. Structures and purity of these new products were confirmed by HRMS, 1H, 13C NMR, IR spectroscopy and crystal X-ray analysis. Optimization of reaction conditions for the preparation of dihydroimidazo[1,2-a]pyridine was studied by using a Keggin-type heteropolyacid catalyst. All the synthesized compounds were evaluated in vitro for their antibacterial and antifungal activities against six pathogenic bacteria and a strain of yeast. Compounds 4d, 7b, and 7d were more potent than the reference drug, against Candida albicans IPA (200). Compounds 4a, 4b, 7a, and 7b possessed the highest inhibitory effect or bactericidal activity against SARM. GRAPHICAL ABSTRACT

[1]  Esraa Z. Mohammed,et al.  Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors. , 2019, European journal of medicinal chemistry.

[2]  B. Ghosh,et al.  Design, synthesis and biological evaluation of 2-(3,4-dimethoxyphenyl)-6 (1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine analogues as antiproliferative agents. , 2019, Bioorganic & medicinal chemistry letters.

[3]  D. Kaminskyy,et al.  Thiazolidinone/thiazole based hybrids - New class of antitrypanosomal agents. , 2019, European journal of medicinal chemistry.

[4]  A. Leite,et al.  Multi-target compounds acting in cancer progression: Focus on thiosemicarbazone, thiazole and thiazolidinone analogues. , 2019, European journal of medicinal chemistry.

[5]  H. Hosseini,et al.  An efficient synthesis of new imidazo[1,2-a]pyridine-6-carbohydrazide and pyrido[1,2-a]pyrimidine-7-carbohydrazide derivatives via a five-component cascade reaction , 2019, RSC advances.

[6]  R. Pedrosa,et al.  Novel selenylated imidazo[1,2-a]pyridines for breast cancer chemotherapy: Inhibition of cell proliferation by Akt-mediated regulation, DNA cleavage and apoptosis. , 2018, Biochemical and biophysical research communications.

[7]  B. Nedjar-Kolli,et al.  Acid-Catalyzed Synthesis of Thiazolidin-4-ones , 2018 .

[8]  L. Saso,et al.  In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole. , 2018, Chemico-biological interactions.

[9]  Ozlem Bingol Ozakpinar,et al.  Tiyoüreler, açiltiyoüreler ve 4-tiyazolidinonların sentezi, karakterizasyonu ve antikanser ve antiviral etkilerinin değerlendirilmesi , 2017 .

[10]  E. Duñach,et al.  Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety , 2015 .

[11]  Honglin Li,et al.  Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives , 2015 .

[12]  Anil Kumar,et al.  Synthesis of 3-aroylimidazo[1,2-a]pyridines via CuCl2 catalyzed tandem dual carbon–nitrogen bonding , 2014 .

[13]  A. Oliver,et al.  Scaffold-switching: an exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates. , 2014, Bioorganic & medicinal chemistry letters.

[14]  Mingyao Liu,et al.  Optimization of 2-(3-(arylalkyl amino carbonyl) phenyl)-3-(2-methoxyphenyl)-4-thiazolidinone derivatives as potent antitumor growth and metastasis agents. , 2014, European journal of medicinal chemistry.

[15]  Rahila,et al.  Synthesis of imidazo[1,2-a]pyridine in the presence of iodine–water catalytic system , 2014 .

[16]  A. Verma,et al.  4-Thiazolidinones: the advances continue…. , 2014, European journal of medicinal chemistry.

[17]  H. Oki,et al.  Structure-based design, synthesis, and evaluation of imidazo[1,2-b]pyridazine and imidazo[1,2-a]pyridine derivatives as novel dual c-Met and VEGFR2 kinase inhibitors. , 2013, Bioorganic & medicinal chemistry.

[18]  Y. Al-Faiyz,et al.  The position of imidazopyridine and metabolic activation are pivotal factors in the antimutagenic activity of novel imidazo[1,2-a]pyridine derivatives. , 2013, European journal of pharmacology.

[19]  M. Salem,et al.  Synthesis and biological evaluation of some novel thiazole compounds as potential anti-inflammatory agents. , 2013, European journal of medicinal chemistry.

[20]  K. Rangappa,et al.  Tandem approach for the synthesis of imidazo[1,2-a]pyridines from alcohols , 2013 .

[21]  Shau-Ping Lin,et al.  Docosahexaenoic acid suppresses the expression of FoxO and its target genes. , 2012, The Journal of nutritional biochemistry.

[22]  M. Bazin,et al.  An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via imidazo[1,2-a]pyridin-2-yl triflate through a Suzuki cross-coupling reaction-direct arylation sequence , 2012 .

[23]  T. Itoh,et al.  Facile Synthesis of 3-(Succinimid-3-yl)-2-oxo-2,3-dihydroimidazo[1,2-a]pyridine Derivatives by Sequential Intra- and Intermolecular Michael Reactions between 2-Aminopyridines and Maleimides , 2011 .

[24]  C. Rabia,et al.  Synthesis of Substituted 1,4-Diazepines and 1,5-Benzodiazepines Using an Efficient Heteropolyacid-Catalyzed Procedure , 2010, Molecules.

[25]  R. Lesyk,et al.  Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety. , 2010, European journal of medicinal chemistry.

[26]  Hamed I. Ali,et al.  Synthesis, antitumor activity and molecular docking study of novel sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives. , 2010, European journal of medicinal chemistry.

[27]  S. Desenko,et al.  New direction in the reaction of thiocarboxamides with N-substituted maleimides , 2009 .

[28]  R. Lesyk,et al.  Synthesis and Anticancer Activity of Novel Nonfused Bicyclic Thiazolidinone Derivatives , 2009 .

[29]  K. Saidi,et al.  Highly efficient conversion of aromatic acylals to 3, 4-dihydropyrimidinones: a new protocol for the Biginelli reaction , 2008 .

[30]  D. Schmatz,et al.  Synthesis and biological activity of imidazopyridine anticoccidial agents: Part II. , 2007, European journal of medicinal chemistry.

[31]  A. Gueiffier,et al.  Recent progress in the pharmacology of imidazo[1,2-a]pyridines. , 2007, Mini reviews in medicinal chemistry.

[32]  K. Gudmundsson,et al.  Imidazo[1,2-a]pyridines with potent activity against herpesviruses. , 2007, Bioorganic & medicinal chemistry letters.

[33]  R. Lesyk,et al.  New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones: synthesis and anticancer evaluation. , 2007, European journal of medicinal chemistry.

[34]  D. Schmatz,et al.  Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents. , 2006, Bioorganic & medicinal chemistry letters.

[35]  E. Mini,et al.  In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I. , 2005, Bioorganic & medicinal chemistry letters.

[36]  M. Bock,et al.  Bradykinin B1 antagonists: SAR studies in the 2,3-diaminopyridine series. , 2005, Bioorganic & medicinal chemistry letters.

[37]  F. Fauvelle,et al.  2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR. , 2005, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[38]  K. Gudmundsson,et al.  Synthesis of novel imidazo[1,2-a]pyridines with potent activity against herpesviruses. , 2003, Organic letters.

[39]  H. Hahn,et al.  A Simple Construction of 2-Phenylimino-1,3-thiazolidin-4-ones , 2001 .

[40]  R. Tyagi,et al.  2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents , 1999 .

[41]  E. Pedersen,et al.  Synthesis and evaluation of antiviral activity of 2′-deoxyuridines with 5-methylene-2-thiohydantoin substituents in the 5-position , 1994 .

[42]  K. James,et al.  A new route to 6-substituted 2,3-diaminopyridines , 1991 .