Synthesis and evaluation of some new 5-(hetaryl)thiazoles as potential antimicrobial agents

References

• Sharma, A.; Suhas, R.; Chandan, S.; Gowda, D. C. Novel Urea and Thiourea Derivatives of Thiazole-Glutamic Acid Conjugate as Potential Inhibitors of Microbes and Fungi. Russ. J. Bioorg. Chem. 2013, 39, 656–664.
   Web of Science ®Google Scholar
• Ayati, A.; Emami, S.; Asadipour, A.; Shafiee, A.; Foroumadi, A. Recent Applications of 1,3-Thiazole Core Structure in the Identification of New Lead Compounds and Drug Discovery. Eur. J. Med. Chem. 2015, 97, 699–718. DOI: 10.1016/j.ejmech.2015.04.015.
   PubMed Web of Science ®Google Scholar
• Nasr, T.; Bondock, S.; Eid, S. Design, Synthesis, Antimicrobial Evaluation and Molecular Docking Studies of Some New 2,3-Dihydrothiazoles and 4-Thiazolidinones Containing Sulfisoxazole. J. Enzym. Inhib. Med. Chem. 2016, 31, 236–246. DOI: 10.3109/14756366.2015.1016514.
   PubMed Web of Science ®Google Scholar
• Makam, P.; Kankanala, R.; Prakash, A.; Kannan, T. 2-(2-Hydrazinyl)thiazole Derivatives: Design, Synthesis and In Vitro Antimycobacterial Studies. Eur. J. Med. Chem. 2013, 69, 564–576. DOI: 10.1016/j.ejmech.2013.08.054.
   PubMed Web of Science ®Google Scholar
• Dawood, K. M.; Eldebss, T. M.; El-Zahabi, H. S.; Yousef, M. H. Synthesis and Antiviral Activity of Some New Bis-1,3-thiazole Derivatives. Eur. J. Med. Chem. 2015, 102, 266–276. DOI: 10.1016/j.ejmech.2015.08.005.
   PubMed Web of Science ®Google Scholar
• Hassan, G. S.; El-Messery, S. M.; Al-Omary, F. A.; El-Subbagh, H. I. Substituted Thiazoles VII. Synthesis and Antitumor Activity of Certain 2-(Substituted amino)-4-phenyl-1,3-thiazole Analogs. Bioorg. Med. Chem. Lett. 2012, 22, 6318–6323. DOI: 10.1016/j.bmcl.2012.08.095.
   PubMed Web of Science ®Google Scholar
• Ghabbour, H. A.; Kadi, A. A.; El-Tahir, K. E. H.; Angawi, R. F.; El-Subbagh, H. I. Synthesis, Biological Evaluation and Molecular Docking Studies of Thiazole-Based Pyrrolidinones and Isoindolinediones as Anticonvulsant Agents. Med. Chem. Res. 2015, 24, 3194–3211. DOI: 10.1007/s00044-015-1371-3.
   Web of Science ®Google Scholar
• Koppireddi, S.; Komsani, J. R.; Avula, S.; Pombala, S.; Vasamsetti, S.; Kotamraju, S.; Yadla, R. Novel 2-(2,4-Dioxo-1,3-thiazolidin-5-yl)acetamides as Antioxidant and/or Anti-Inflammatory Compounds. Eur. J. Med. Chem. 2013, 66, 305–313. DOI: 10.1016/j.ejmech.2013.06.005.
   PubMed Web of Science ®Google Scholar
• Lee, Y. S.; Kim, H.; Kim, Y. H.; Roh, E. J.; Han, H.; Shin, K. J. Synthesis and Structure–Activity Relationships of Tri-Substituted Thiazoles as RAGE Antagonists for the Treatment of Alzheimer’s Disease. Bioorg. Med. Chem. Lett. 2012, 15, 7555–7561. DOI: 10.1016/j.bmcl.2012.10.022.
   Web of Science ®Google Scholar
• Bondock, S.; Albormani, O.; Fouda, A. M.; Safieh, K. A. Recent Progress in the Chemistry of 5-Acetylthiazoles. Synth. Commun. 2016, 46, 1081–1117. DOI: 10.1080/00397911.2016.1180700.
   Web of Science ®Google Scholar
• Albuquerque, H. M. T.; Santos, C. M. M.; Cavaleiro, J. A. S.; Silva, A. M. S. Chalcones as Versatile Synthons for the Synthesis of 5- and 6-Membered Nitrogen Heterocycles. Curr. Org. Chem. 2014, 18, 2750–2775. DOI: 10.2174/1385272819666141013224253.
   Web of Science ®Google Scholar
• Lin, Y. M.; Zhou, Y.; Flavin, M. T.; Zhou, L. M.; Nie, W.; Chen, F. C. Chalcones and Flavonoids as Anti-Tuberculosis Agents. Bioorg. Med. Chem. 2002, 10, 2795–2802. DOI: 10.1016/s0968-0896(02)00094-9.
   PubMed Web of Science ®Google Scholar
• Lopez, S. N.; Castelli, M. V.; Zacchino, S. A.; Dominguez, J. N. In Vitro Antifungal Evaluation and Structure–Activity Relationships of a New Series of Chalcone Derivatives and Synthetic Analogues, with Inhibitory Properties Against Polymers of the Fungal Cell Wall. Bioorg. Med. Chem. 2001, 9, 1999–2013. DOI: 10.1016/s0968-0896(01)00116-x.
   PubMed Web of Science ®Google Scholar
• Won, S. J.; Cheng, C. T.; Tsao, L. T.; Weng, J. R.; Ko, H. H.; Wang, J. P.; Lin, C. N. Synthetic Chalcones as Potential Anti-Inflammatory and Cancer Chemopreventive Agents. Eur. J. Med. Chem. 2005, 40, 103–112. DOI: 10.1016/j.ejmech.2004.09.006.
   PubMed Web of Science ®Google Scholar
• Hassan, S. Y. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules 2013, 18, 2683–2711. DOI: 10.3390/molecules18032683.
   PubMed Web of Science ®Google Scholar
• El-Sabbagh, O. I.; Baraka, M. M.; Ibrahim, S. M.; Pannecouque, C.; Andrei, G.; Snoeck, R.; Balzarini, J.; Rashad, A. A. Synthesis and Antiviral Activity of New Pyrazole and Thiazole Derivatives. Eur. J. Med. Chem. 2009, 44, 3746–3753. DOI: 10.1016/j.ejmech.2009.03.038.
   PubMed Web of Science ®Google Scholar
• Abdel Gawad, N. M.; Georgey, H. H.; Ibrahim, N. A.; Amin, N. H.; Abdelsalam, R. M. Synthesis of Novel Pyrazole and Dihydropyrazoles Derivatives as Potential Anti-Inflammatory and Analgesic Agents. Arch. Pharm. Res. 2012, 35, 807–821. DOI: 10.1007/s12272-012-0507-y.
   PubMed Web of Science ®Google Scholar
• Amir, M.; Kumar, H.; Khan, S.-A. Synthesis and Pharmacological Evaluation of Pyrazoline Derivatives as New Anti-Inflammatory and Analgesic Agents. Bioorg. Med. Chem. Lett. 2008, 18, 918–922. DOI: 10.1016/j.bmcl.2007.12.043.
   PubMed Web of Science ®Google Scholar
• Prasad, Y. R.; Rao, A. L.; Prasoona, L.; Murali, K.; Kumar, P. R. Synthesis and Antidepressant Activity of Some 1,3,5-Triphenyl-2-pyrazolines and 3-(2(-Hydroxy naphthalen-1(-yl)-1,5-diphenyl-2-pyrazolines. Bioorg. Med. Chem. Lett. 2005, 15, 5030–5034. DOI: 10.1002/chin.200607129.
   PubMed Web of Science ®Google Scholar
• Özdemir, Z.; Kandilci, H.-B.; Gümüşel, B.; Çalış, U.; Bilgin, A.-A. Synthesis and Studies on Antidepressant and Anticonvulsant Activities of Some 3-(2-Furyl)-pyrazoline Derivatives. Eur. J. Med. Chem. 2007, 42, 373–379. DOI: 10.1016/j.ejmech.2006.09.006.
   PubMed Web of Science ®Google Scholar
• Shaharyar, M.; Siddiqui, A.-A.; Ali, M.-M.; Sriram, D.; Yogeeswari, P. Synthesis and In Vitro Antimycobacterial Activity of N1-Nicotinoyl-3-(4(-hydroxy-3(-methylphenyl)-5-[(sub)phenyl]-2-pyrazolines. Bioorg. Med. Chem. Lett. 2006, 16, 3947–3949. DOI: 10.1016/j.bmcl.2006.05.024.
   PubMed Web of Science ®Google Scholar
• Abid, M.; Azam, A. Synthesis, Characterization, and Antiamoebic Activity of 1-(Thiazolo[4,5-b]quinoxaline-2-yl)-3-phenyl-2-pyrazoline Derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 2812–2816. DOI: 10.1002/chin.200634158.
   PubMed Web of Science ®Google Scholar
• Gurdere, M. B.; Gumus, O.; Yaglioglu, A. S.; Budak, Y.; Ceylan, M. Synthesis and Anticancer Activities of 1,4-Phenylene-bis-N-acetyl- and N-Phenylpyrazoline Derivatives. Res. Chem. Intermed. 2017, 43, 1277–1289. DOI: 10.1007/s11164-016-2697-2.
   Web of Science ®Google Scholar
• Bondock, S.; Khalifa, W.; Fadda, A. A. Synthesis and Antimicrobial Evaluation of Some New Thiazole, Thiazolidinone, and Thiazoline Derivatives Starting from 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur. J. Med. Chem. 2007, 42, 948–954. DOI: 10.1016/j.ejmech.2006.12.025.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Rabie, R.; Etman, H. A.; Fadda, A. A. Synthesis and Antimicrobial Activity of Some New Heterocycles Incorporating Antipyrine Moiety. Eur. J. Med. Chem. 2008, 43, 2122–2129. DOI: 10.1016/j.ejmech.2007.12.009.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Fadaly, W.; Metwally, M. A. Enaminonitrile in Heterocyclic Synthesis: Synthesis and Antimicrobial Evaluation of Some New Pyrazole, Isoxazole and Pyrimidine Derivatives Incorporating a Benzothiazole Moiety. Eur. J. Med. Chem. 2009, 44, 4813–4818. DOI: 10.1016/j.ejmech.2009.07.024.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Fadaly, W.; Metwally, M. A. Synthesis and Antimicrobial Activity of Some New Thiazole, Thiophene and Pyrazole Derivatives Containing Benzothiazole Moiety. Eur. J. Med. Chem. 2010, 45, 3692–3701. DOI: 10.1016/j.ejmech.2010.05.018.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Khalifa, W.; Fadda, A. A. Synthesis and Antimicrobial Activity of Some New 4-Hetarylpyrazole and Furo[2,3-c]pyrazole Derivatives. Eur. J. Med. Chem. 2011, 46, 2555–2561. DOI: 10.1016/j.ejmech.2011.03.045.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Naser, T.; Ammar, Y. A. Synthesis of Some New 2-(3-Pyridyl)-4,5-disubstituted Thiazoles as Potent Antimicrobial Agents. Eur. J. Med. Chem. 2013, 62, 270–279. DOI: 10.1016/j.ejmech.2012.12.050.
   PubMed Web of Science ®Google Scholar
• Nasr, T.; Bondock, S.; Eid, S. Design, Synthesis, Antimicrobial Evaluation and Molecular Docking Studies of Some New Thiophene, Pyrazole and Pyridone Derivatives Bearing Sulfisoxazole Moiety. Eur. J. Med. Chem. 2014, 84, 491–504. DOI: 10.1016/j.ejmech.2014.07.052.
   PubMed Web of Science ®Google Scholar
• Bondock, S. Synthesis and Antimicrobial Evaluation of Novel Polyheterocyclic Ring Systems Derived from 2-Oxo-2H-pyrimido[2,1-b]benzothiazole-3-carbonitrile. Res. Chem. Intermed. 2015, 41, 5451–5462. DOI: 10.1007/s11164-014-1672-z.
   Web of Science ®Google Scholar
• Bondock, S.; Gieman, H. Synthesis, Antibacterial and Anticancer Evaluation of Some New 2-Chloro-3-hetarylquinolines. Res. Chem. Intermed. 2015, 41, 8381–8403. DOI: 10.1007/s11164-014-1899-8.
   Web of Science ®Google Scholar
• Bondock, S.; El-Azab, H.; Knadeel, E.-E. M.; Metwally, M. A. Efficient Synthesis of New Functionalized 2-(Hetaryl)thiazoles. Synth. Commun. 2013, 43, 59–71. DOI: 10.1002/chin.201321145.
   Web of Science ®Google Scholar
• Wang, S.; Meades, C.; Wood, G.; Qsnowski, A.; Anderson, S.; Yuill, R.; Thomas, M.; Menza, M.; Jackson, W.; Midgley, C.; et al. 2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors: Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity. J. Med. Chem. 2004, 47, 1662–1675. DOI: 10.1021/jm0309957.
   PubMed Web of Science ®Google Scholar
• El-Hashash, M. A.; Gomha, S. M.; El-Arab, E. E. Utility of Pyrazolylchalcone Synthon to Synthesized Azolopyrimidines Under Grindstone Technology. Chem. Pharm. Bull. 2017, 65, 90–96. DOI: 10.1248/cpb.c16-00759.
   PubMed Web of Science ®Google Scholar
• Bhalerao, M. B.; Dhumal, S. T.; Deshmukh, A. R.; Nawale, L. U.; Khedkar, V.; Sarkar, D.; Mane, R. A. New Bithiazolyl hydrazones: Novel Synthesis, Characterization and Antitubercular Evaluation. Bioorg. Med. Chem. Lett. 2017, 27, 288–294. DOI: 10.1016/j.bmcl.2016.11.056.
   PubMed Web of Science ®Google Scholar
• Althagafi, I.; Elghalban, M. G.; Saad, F.; Al-Fahemi, J. H.; El-Metwally, N. M.; Bondock, S.; Almazroaia, L.; Saleh, K. A.; Al-Hazmi, G. A. Spectral Characterization, CT-DNA Binding, DFT/B3LYP, Molecular Docking and Antitumor Studies for New Nano-Sized VO(II)-hydrazonoyl Complexes. J. Mol. Liq. 2017, 242, 662–677. DOI: 10.1016/j.molliq.2017.06.113.
   Web of Science ®Google Scholar
• Shamroukh, A. H.; Zaki, M. E. A.; Morsy, E. M. H.; Abdel-Motti, F. M.; Abdel-Megeid, F. M. E. Synthesis, Isomerization, and Antimicrobial Evaluation of Some Pyazolopyranotriazolopyrimidine Derivatives. Arch. Pharm. Chem. Life Sci. 2007, 340, 345–351. DOI: 10.1002/ardp.200700007.
   PubMed Web of Science ®Google Scholar