SYNTHESIS AND CHARACTERIZATION OF HETEROCYCLIC CHALCONES CONTAINING HALOGENATED THIOPHENES
DOI:
https://doi.org/10.11113/jt.v77.6005Keywords:
Heterocyclic Chalcone, Claisen-Schmidt condensation, Halogenated thiopheneAbstract
Heterocyclic chalcones containing halogenated thiophenes were synthesized. The first step was to synthesize 3-acetyl-2,5-dichlorothiophene and 2-acetyl-5-chlorothiophene as heterocyclic ketones by using Friedel-Crafts acylation. The ketones were then used to synthesize thiophene chalcones through Claisen-Schmidt reaction with the respective heterocyclic aldehydes such as 5-bromothiophene-2-carbaldehyde, 3-methyl-2-thiophene carboxaldehyde and 2-thiophene carboxaldehyde with 3-acetyl-2,5-dichlorothiophene or 2-acetyl-5-chlorothiophene in presence of basic medium, sodium hydroxide to form the corresponding chalcones. Structures of the synthetic compounds were confirmed by IR, MS, 1H and 13C NMR spectral data.
References
Rahman, A. U. 2013. Studies in Natural Products Chemistry. 1st ed. Kidlingon Oxford: Elsevier. 49.
Silva, W. A., Andrade, C. K. Z., Napolitano, H. B., Vencato, I., Lariucci, C., Castro, M. and Camargo, A. J. 2013. Biological and Structure Activity Evaluation of Chalcone Derivatives Against Bacteria and Fungi. Journal of the Brazilian Chemical Society. 24: 133-144.
Won, S. J., Liu, C. T., Tsao, L. T., Weng, J. R., Ko, H. H., Wang, J. P. and Lin, C. N. 2005. Synthetic Chalcones as Potential Anti-inflammatory and Cancer Chemopreventive Agents. European Journal of Medicinal Chemistry. 40: 103-112.
Vogel, S., Barbic, M., JurgenlIemk, G. and Heilmann, J. 2010. Synthesis, Cytotoxicity, Anti-oxidative and Anti-inflammatory Activity of Chalcones and Influence of A-ring Modifications on the Pharmacological Effect. European Journal of Medicinal Chemistry. 45: 2206-2213.
Kayser, O. and Kiderlen, A. F. 2001. In Vitro Leishmanicidal Activity of Naturally Occurring Chalcones. Phytotherapy Research.15: 148-152.
Aponte, J. C., Castillo, D., Estevez, Y., Gonzalez, G., Arevalo, J., Hammond, G. B. and Sauvain, M. 2010. In Vitro and in Vivo Anti-Leishmania Activity of Polysubstituted Synthetic Chalcones. Bioorganic and Medicinal Chemistry Letters. 20: 100-103.
Mello, T. P., Bitencourt, H., Pedroso, R., Aristides, S. M., Lonardoni, M. C. and Silveira, T.V. 2014. Leishmanicidal activity of synthetic chalcones in Leishmania (Viannia) Braziliensis. Experimental Parasitology. 136: 27-34.
Wu, X., Wilairat, P. and Go, M. L. 2002. Antimalarial Activity of Ferrocenyl Chalcones. Bioorganic and Medicinal Chemistry Letters. 12: 2299-2302.
Tadigoppula, N., Korthikunta, V., Gupta, S., Kancharla, P., Khaliq, T., Soni, A., Srivastava, R. K., Srivastava, K., Puri, S. K. and Raju, K. S. R. 2012. Synthesis and Insight into The Structure Activity Relationships of Chalcones as Antimalarial Agents. Journal of Medicinal Chemistry. 56: 31-45.
Ameta, K., Kumar, B. and Rathore, N. S. 2011. Microwave Induced Improved Synthesis of some Novel Substituted 1,3-Diarylpropenones and their Anti-microbial Activity. Journal of Chemistry. 8: 665-670.
Ahmad, M. R., Sastry, V. G. and Bano, N. 2011. Synthesis and Cytotoxic, Anti-oxidant Activity of 1,3-Diphenyl-2-propene-1-oneDerivatives. International Journal of ChemTech Research. 3: 1462-1469.
Doan, T. N. and Tran, D. T. 2011. Synthesis, Antioxidant and Antimicrobial Activities of a Novel Series of Chalcones, Pyrazolic Chalcones, and Allylic Chalcones. Pharmacology and Pharmacy. 2: 282-288.
Bandgar, B. P., Gawande, S. S., Bodade, R. G., Totre, J. V. and Khobragade, C. N. 2010. Synthesis and Biological Evaluation of Simple Methoxylated Chalcones as Anticancer, Anti-inflammatory and Antioxidant Agents. Bioorganic and Medicinal Chemistry. 18: 1364-1370.
Syam, S., Abdelwahab, S. I., Al-mamary, M. A. and Mohan, S. 2012. Synthesis of Chalcones with Anticancer Activities. Molecules. 17: 6179-6195.
Wu, J. H., Wang, X. H., Yi, Y. H. and Lee, K. H. 2010. Anti-AIDS Agents 54. A potent Anti-HIV Chalcone and Flavonoids from Genus Desmos.Molecules. 10: 2145-2156.
Cheenpracha, S., Karalai, C., Ponglimanont, C., Subhadhirasakul, S. and Tewtrakul, S. 2006. Anti-HIV-1 Protease Activity of Compounds from BoesenbergiaPandurata. Bioorganic and Medicinal Chemistry. 14: 1710-1714.
Asiri, A. M. and Khan, S. A. 2011. Synthesis and Anti-bacterial Activities of a Bis-Chalcone Derived from Thiophene and its Bis-Cyclized Products. Molecules. 16: 523-531.
Rao, N. S., Kistareddy, C., Bhavani, B. and Bhavani, R. 2013. Synthesis, Antibacterial and Antifungal Activity of some Novel Chalcone Derivatives Derived from Apocynin. Chemistry Journal. 3(6): 143-148.
Kumar, C., Loh, W.-S., Ooi, C. W., Quah, C. K. and Fun, H.-K. 2013. Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation. Molecules. 18: 12707-12724.
Bohm, B. A. 1998. Introduction to Flavonoids. 1st ed. London: Harwood Academic Publishers. 243-284.
Eddarir, S., Cotelle, N., Bakkour, Y. and Rolando, C. 2003. An Efficient Synthesis of Chalcones Based on the Suzuki Reaction. Tetrahedron Letters. 44: 5359-5363.
Juvale, K., Pape, V. F. and Wiese, M. 2012. Investigation of Chalcones and Benzochalcones as Inhibitors of Breast Cancer Resistance Protein. Bioorganic and Medicinal Chemistry. 20: 346-355.
Jayapal, M. and Sreedhar, N. 2010. Anhydrous K2CO3 as Catalyst for the Synthesis of Chalcones Under Microwave Irradiation. Journal of Pharmaceutical Science and Research. 2: 644-647.
Li, J. T., Yang, W. Z., Wang, S. X., Li, S. H. and Li, T. 2002. Improved Synthesis of Chalcones Under Ultrasound Irradiation. UltrasonicsSonochemistry. 9: 237-239.
Zangade, S., Mokle, S., Vibhute, A. and Vibhute, Y. 2011. An Efficient and Operationally Simple Synthesis of some New Chalcones by Using Grinding Technique. Journal of Chemical Sciences. 13: 1-6.
Narender, T. a Papi Reddy, K. 2007. A Simple and Highly Efficient Method for the Synthesis of Chalcones by Using Boron Trifluoride Etherate. Tetrahedron Letters. 48: 3177-3180.
Kaur, N. and Kishore, D. 2013. Application of Chalcones in Heterocycles Synthesis: Synthesis of 2-(isoxazolo, pyrazolo and pyrimido) Substituted Analogues of 1,4-benzodiazepin-5-carboxamides Linked Through an Oxyphenyl Bridge. Journal of Chemical Sciences. 125: 555-560.
Ãvila, H. P., Smania, E. D. F. A., Monache, F. D. and SmaniaJúnior, A. 2008. Structure Activity Relationship of Antibacterial Chalcones. Bioorganic and Medicinal Chemistry. 16: 9790-9794.
Hartough, H. D. and Conley, L. G. 1947. Acylation Studies in the Thiophene and Furan Series. V. Thiophene Carboxylic Acids and Semicarbazones Derived from Acetylthiophenes. Journal of the American Chemical Society. 69: 3096-3098.
Dannhardt, G., Kiefer, W., Krämer, G., Maehrlein, S., Nowe, U. and Fiebich, B. 2000. The Pyrrole Moiety as a Template for COX-1/COX-2 Inhibitors.European Journal of Medicinal Chemistry. 35: 499-510.
Al-Maqtari Helmi Mohammed. 2011. Synthesis of Some New2-Oxo-6-thieno-2-yl-4,6-heteroaromatic-1,2-dihydropyridine-3-carbonitrile Derivatives. Master Thesis. Al al-Bayt University, Jordan.
Buu-Hoi, Ng. Ph., Xuong, Ng. Dat and Sy, Michel. 1956. Chalcone Derivatives of Thiophene and Their Thiosemicarbaz. Bulletin de la Societe Chimique de France.1: 1646-1650.
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