Synthesis and Antibacterial Activity of New Imidazo[1,2-a]pyridines Festooned with Pyridine, Thiazole or Pyrazole Moiety

References

• A. R. Katritzky, Y.-J. Xu, and H. Tu, “Regiospecific Synthesis of 3-Substituted Imidazo[1,2-a]Pyridines, Imidazo[1,2-a]Pyrimidines, and Imidazo[1,2-c]Pyrimidine,” The Journal of Organic Chemistry 68, no. 12 (2003): 4935–7.
   PubMed Web of Science ®Google Scholar
• N. Chernyak and V. Gevorgyan, “General and Efficient Copper‐Catalyzed Three‐Component Coupling Reaction towards Imidazoheterocycles: One‐Pot Synthesis of Alpidem and Zolpidem,” Angewandte Chemie 122, no. 15 (2010): 2803–6.
   Google Scholar
• I. Vliegen, J. Paeshuyse, T. De Burghgraeve, L. S. Lehman, M. Paulson, I.-H. Shih, E. Mabery, N. Boddeker, E. De Clercq, H. Reiser, et al. “Substituted Imidazopyridines as Potent Inhibitors of HCV Replication,” Journal of Hepatology 50, no. 5 (2009): 999–1009.
   PubMed Web of Science ®Google Scholar
• R. Ducray, I. Simpson, F. H. Jung, J. W. M. Nissink, P. W. Kenny, M. Fitzek, G. E. Walker, L. T. Ward, and K. Hudson, “Discovery of Novel Imidazo[1,2-a]Pyridines as Inhibitors of the Insulin-like Growth Factor-1 Receptor Tyrosine Kinase,” Bioorganic & Medicinal Chemistry Letters 21, no. 16 (2011): 4698–701.
   PubMed Web of Science ®Google Scholar
• S. Kazzouli, A. Griffon Du Bellay, S. Berteina-Raboin, P. Delagrange, C. Daniel-Henry, and G. Guillaumet, “Design and Synthesis of 2-Phenylimidazo[1,2-a]Pyridines as a Novel Class of Melatonin Receptor Ligands,” European Journal of Medicinal Chemistry 46, no. 9 (2011): 4252–7.
   PubMed Web of Science ®Google Scholar
• A. Kamal, G. Ramakrishna, M. Janaki Ramaiah, A. Viswanath, A. V. Subba Rao, Ch. Bagul, De Mukhopadyay, S. N. C. V. L. Pushpavalli, and M. Pal-Bhadra, “Design, Synthesis and Biological Evaluation of Imidazo[1,5-a]Pyridine–PBD Conjugates as Potential DNA-Directed Alkylating Agents,” MedChemComm 4, no. 4 (2013): 697–703.
   Web of Science ®Google Scholar
• D. W. Engers, S. R. Bollinger, A. S. Felts, A. K. Vadukoot, C. Williams, A. L. Blobaum, C. W. Lindsley, C. C. Hong, and C. R. Hopkins, “Discovery, Synthesis and Characterization of a Series of 7-Aryl-Imidazo[1,2-a]Pyridine-3-Ylquinolines as Activin-like Kinase (ALK) Inhibitors,” Bioorganic & Medicinal Chemistry Letters 30no. 18 (2020): 127418.
   PubMed Web of Science ®Google Scholar
• M. Adib, E. Sheikhi, and N. Rezaei, “One-Pot Synthesis of Imidazo[1,2-a]Pyridines from Benzyl Halides or Benzyl Tosylates, 2-Aminopyridines and Isocyanides,” Tetrahedron Letters 52, no. 25 (2011): 3191–4.
   Web of Science ®Google Scholar
• K. C. Rupert, J. R. Henry, J. H. Dodd, S. A. Wadsworth, D. E. Cavender, G. C. Olini, B. Fahmy, and J. J. Siekierka, “Imidazopyrimidines, Potent Inhibitors of p38 MAP Kinase,” Bioorganic & Medicinal Chemistry Letters 13, no. 3 (2003): 347–50.
   PubMed Web of Science ®Google Scholar
• R. B. Lacerda, C. K. de Lima, L. L. da Silva, N. C. Romeiro, A. L. P. Miranda, E. J. Barreiro, and C. A. M. Fraga, “Discovery of Novel Analgesic and anti-inflammatory 3-arylamine-imidazo[1,2-a]pyridine symbiotic prototypes,” Bioorganic & Medicinal Chemistry17, no. 1 (2009): 74–84.
   PubMed Web of Science ®Google Scholar
• M. A. Ismail, R. K. Arafa, T. Wenzler, R. Brun, F. A. Tanious, W. D. Wilson, and D. W. Boykin, “Synthesis and Antiprotozoal Activity of Novel Bis-Benzamidino Imidazo[1,2-a]Pyridines and 5,6,7,8-Tetrahydro-Imidazo[1,2-a]Pyridines,” Bioorganic & Medicinal Chemistry 16, no. 2 (2008): 683–91.
   PubMed Web of Science ®Google Scholar
• T. Biftu, D. Feng, M. Fisher, G.-B. Liang, X. Qian, A. Scribner, R. Dennis, S, Lee, P. A. Liberator, C. Brown, et al. “Synthesis and SAR Studies of Very Potent Imidazopyridine Antiprotozoal Agents,” Bioorganic & Medicinal Chemistry Letters 16, no. 9 (2006): 2479–83.
   PubMed Web of Science ®Google Scholar
• M. Taha, N. H. Ismail, S. Imran, H. Rashwan, W. Jamil, S. Ali, S. M. Kashif, F. Rahim, U. Salar, and K. M. Khan, “Synthesis of 6-Chloro-2-Aryl-1H-Imidazo[4,5-b]Pyridine Derivatives: Antidiabetic, Antioxidant, β-Glucuronidase Inhibiton and Their Molecular Docking Studies,” Bioorganic Chemistry 65, (2016): 48–56.
   PubMed Web of Science ®Google Scholar
• A. Elhakmaoui, A. Gueiffier, J.-C. Milhavet, Y. Blache, J.-P. Chapat, O. Chavignon, J.-C. Teulade, R. Snoeck, G. Andrei, and E. De Clercq, “Synthesis and Antiviral Activity of 3-Substituted Imidazo[1,2-a]Pyridines,” Bioorganic & Medicinal Chemistry Letters 4, no. 16 (1994): 1937–40.
   Web of Science ®Google Scholar
• G. Puerstinger, J. Paeshuyse, E. De Clercq, and J. Neyts, “Antiviral 2,5-Disubstituted Imidazo[4,5-c]Pyridines: From anti-Pestivirus to anti-Hepatitis C Virus Activity,” Bioorganic & Medicinal Chemistry Letters 17, no. 2 (2007): 390–3.
   PubMed Web of Science ®Google Scholar
• J. J. Kaminsky, C. Puchalski, D. M. Solomon, R. K. Rizvi, D. J. Conn, A. J. Elliot, R. G. Lovey, Guzik, P J S. Chui, J. F. Long, et al. “Antiulcer Agents. 4. Conformational Considerations and the Antiulcer Activity of Substituted imidazo[1,2-a]pyridines and related analogues ,”Journal of Medicinal Chemistry 32, no. 8 (1989): 1686–700. no.
   PubMed Web of Science ®Google Scholar
• J. J. Kaminski and A. M. Doweyko, “Antiulcer Agents. 6. Analysis of the in Vitro Biochemical and in Vivo Gastric Antisecretory Activity of Substituted Imidazo[1,2-a]Pyridines and Related Analogues Using Comparative Molecular Field Analysis and Hypothetical Active Site Lattice Methodologies,” Journal of Medicinal Chemistry 40, no. 4 (1997): 427–36..
   PubMed Web of Science ®Google Scholar
• S. Kumar, N. Sharma, I. K. Maurya, A. K. Bhasin, N. Wangoo, P. Brandão, V. Félix, K. K. Bhasin, and R. K. Sharma, “Facile Synthesis, Structural Evaluation, Antimicrobial Activity and Synergistic Effects of Novel Imidazo[1,2-a]Pyridine Based Organoselenium Compounds,” European Journal of Medicinal Chemistry 123, (2016): 916–24.
   PubMed Web of Science ®Google Scholar
• T. H. Al-Tel, R. A. Al-Qawasmeh, and R. Zaarour, “Design, Synthesis and in Vitro Antimicrobial Evaluation of Novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs ,”European Journal of Medicinal Chemistry 46, no. 5 (2011): 1874–81.
   PubMed Web of Science ®Google Scholar
• N. Devi, A. K. Jana, and V. Singh, “Assessment of Novel Pyrazolopyridinone Fused Imidazopyridines as Potential Antimicrobial Agents,” Karbala International Journal of Modern Science 4, no. 1 (2018): 164–70.
   Google Scholar
• K. S. Gudmundsson, and B. A. Johns, “Imidazo[1,2-a]Pyridines with Potent Activity against Herpesviruses,”Bioorganic & Medicinal Chemistry Letters 17, no. 10 (2007): 2735–9.
   PubMed Web of Science ®Google Scholar
• J. B. Véron, C. Enguehard-Gueiffier, R. Snoeck, G. Andrei, E. De. Clercq, and A. Gueiffier, “Influence of 6 or 8-Substitution on the Antiviral Activity of 3-Phenethylthiomethylimidazo[1,2-a]Pyridine against Human Cytomegalovirus (HCMV) and Varicella-Zoster Virus (VZV),” Bioorganic & Medicinal Chemistry 15, no. 22 (2007): 7209–19.
   PubMed Web of Science ®Google Scholar
• S. Chitti, S. Singireddi, P. S. K. Reddy, P. Trivedi, Y. Bobde, C. Kumar, K. Rangan, B. Ghosh, and K. V. G. C. Sekhar, “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, ”Bioorganic & Medicinal Chemistry Letters 29, no. 18 (2019): 2551–8.
   PubMed Web of Science ®Google Scholar
• M. L. Bode, D. Gravestock, S. S. Moleele, C. W. van der Westhuyzen, S. C. Pelly, P. A. Steenkamp, H. C. Hoppe, T. Khan, and L. A. Nkabinde, “Imidazo[1,2-a]Pyridin-3-Amines as Potential HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors,” Bioorganic & Medicinal Chemistry 19, no. 14 (2011): 4227–37.
   PubMed Web of Science ®Google Scholar
• S. Renard, A. Olivier, P. Granger, P. Avenet, D. Graham, M. Sevrin, P. George, and F. Besnard, “Structural Elements of the γ-Aminobutyric Acid Type a Receptor Conferring Subtype Selectivity for Benzodiazepine Site Ligands,” The Journal of Biological Chemistry 274, no. 19 (1999): 13370–4.
   PubMed Web of Science ®Google Scholar
• H. Depoortere, B. Zivkovic, K. G. Lloyd, D. J. Sanger, G. Perrault, S. Z. Langer, and G. Bartholini, “Zolpidem, a Novel Nonbenzodiazepine Hypnotic. I. Neuropharmacological and Behavioral Effects,” Journal of Pharmacology and Experimental Therapeutics 237, no. 2 (1986): 649–58.
   PubMed Web of Science ®Google Scholar
• K. Mizushige, T. Ueda, K. Yukiiri, and H. Suzuki, “Olprinone: A Phosphodiesterase III Inhibitor with Positive Inotropic and Vasodilator Effects,” Cardiovascular Drug Reviews 20, no. 3 (2002): 163–74.
   PubMedGoogle Scholar
• Y. Zhang, Z. Chen, W. Wu, Y. Zhang, and W. Su, “CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles,” The Journal of Organic Chemistry 78, no. 24 (2013): 12494–504.
   PubMed Web of Science ®Google Scholar
• R. D. Li, H. L. Wang, Y. B. Li, Z. Q. Wang, X. Wang, Y. T. Wang, Z. M. Ge, and R. T. Li, “Discovery and Optimization of Novel Dual Dithiocarbamates as Potent Anticancer Agents,” European Journal of Medicinal Chemistry 93, (2015): 381–91.
   PubMed Web of Science ®Google Scholar
• R. M. Mohareb and N. Y. M. Abdo, “Synthesis and Cytotoxic Evaluation of Pyran, Dihydropyridine and Thiophene Derivatives of 3-Acetylcoumarin,” Chemical & Pharmaceutical Bulletin 63, no. 9 (2015): 678–87.
   PubMed Web of Science ®Google Scholar
• E. Abdel-Latif, M. M. Fahad, A. El-Demerdash, and M. A. Ismail, “Synthesis and Biological Evaluation of Some Heterocyclic Scaffolds Based on the Multifunctional N‐(4‐Acetylphenyl)‐2‐Chloroacetamide,”Journal of Heterocyclic Chemistry 57, no. 8 (2020): 3071–81.
   Web of Science ®Google Scholar
• S. Bondock, and A. M. Fouda, “Synthesis and Evaluation of Some New 5-(Hetaryl)Thiazoles as Potential Antimicrobial Agents,” Synthetic Communications 48, no. 5 (2018): 561–73.
   Web of Science ®Google Scholar
• H. M. Mohamed, A. H. Abd El-Wahab, K. A. Ahmed, A. M. El-Agrody, A. H. Bedair, F. A. Eid, and M. M. Khafagy, “Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives,” Molecules (Basel, Switzerland) 17, no. 1 (2012): 971–88.
   PubMed Web of Science ®Google Scholar
• E. Abdel-Latif, E. M. Keshk, A. G. M. Khalil, A. Saeed, and H. M. Metwally, “Synthesis, Characterization, and Anticancer Activity (MCF‐7) of Some Acetanilide‐Based Heterocycles,” Journal of Heterocyclic Chemistry 55, no. 10 (2018): 2334–41.
   Web of Science ®Google Scholar
• G. S. Masaret, “A New Approach for the Synthesis and Biological Activities of Novel Thiazolyl‐Pyrazole Derivatives,” ChemistrySelect 6, no. 5 (2021): 974–82.
   Web of Science ®Google Scholar
• A. H. Shamroukh, M. E. A. Zaki, E. M. H. Morsy, F. M. Abdel-Motti, and F. M. E. Abdel-Megeid, “Synthesis, Isomerization, and Antimicrobial Evaluation of Some Pyrazolopyranotriazolopyrimidine Derivatives,”Archiv Der Pharmazie 340, no. 7 (2007): 345–51.
   PubMed Web of Science ®Google Scholar