Design and Synthesis of Chalcone and Chromone Derivatives as Antimicrobial Agents
Main Article Content
Keywords
Chalcones, Chromones, Antimicrobial activity
Abstract
Coumarins are secondary plant metabolites that have significant pharmacological effects. Examples of their 3-substituted derivatives with antibacterial properties include numerobiocin, coumaromycin, and chartencin. In this study, coumarinyl chalcone was synthesized by combining three acetylcoumarins with an aromatic aldehyde using the Pachmann reaction. Compounds (Z2-Z4) were produced and then reacted with hydrazine hydrate to create compounds (Z5-Z7). The synthesized compounds were evaluated for various pharmacological activities, including anti-inflammatory and antibacterial activity using TLC, melting point, IR, and 1H-NMR spectral studies. Compound (Z6) showed good antibacterial activities.
References
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2. Nowakowska, Z., A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem. 2007, 42, 125-137.
3. Burlando, B.; Verotta, L.; Cornara, L.; Bottini-Massa, E., Herbal Principles in Cosmetics: Properties and Mechanisms of Action ,CRC Press, Taylor & Francis Group: Boca Raton, FL, USA, 2010.
4. Gong, J. X.; Huang, K. X.; Wang, F.; Yang, L. X.; Feng, Y. B.; Li, H. B.; Li, X. K.; Zeng, S.; Wu, X. M.; Stoeckigt, J.; Zhao, Y.; Qu, J., Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage. Bioorg. Med. Chem. 2009, 17, 3414-3425.
5. Dimmock, J. R.; Elias, D. W.; Beazely, M. A.; Kandepu, N. M., Bioactivities of chalcones. Curr. Med. Chem. 1999, 6, 1125-1149.
6. Hadfield, J. A.; Ducki, S.; Hirst, N.; McGown, A. T., Progress in Cell Cycle Research. Editions Life in Progress: New York, 2003; Vol. 5, p 309-325.
7. Bandgar, B. P.; Gawande, S. S.; Bodade, R. G.; Totre, J. V.; Khobragade, C. N., Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg. Med. Chem. 2010, 18, 1364-1370.
8. Patil, C. B.; Mahajan, S. K.; Katti, S. A., Chalcone: A Versatile Molecule. J. Pharm. Sci. Res. 2009, 1, 11-22.
9. Claisen, L.; Claparéde, A., Condensationen von Ketonen mit Aldehyden. Chem. Ber. 1881, 14, 2460-2468.
10. Schmidt, J. G., Ueber die Einwirkung von Aceton auf Furfurol und auf Bittermandelöl bei Gegenwart von Alkalilauge. Chem. Ber. 1881, 14, 1459-1461.
11. Joule, J. A.; Mills, K., Heterocyclic Chemistry. 5th ed.; Chichester, United Kingdom, 2010.
12. Horton, D. A.; Bourne, G. T.; Smythe, M. L., The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev. 2003, 103, 893-930.
13. Evans, B. E.; Rittle, K. E.; Bock, M. G.; Dipardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J., Methods for Drug Discovery - Development of Potent, Selective, Orally Effective Cholecystokinin Antagonists. J. Med. Chem. 1988, 31, 2235-2246.
14. Bhatnagar, S.; Sahi, S.; Kackar, P.; Kaushik, S.; Dave, M. K.; Shukla, A.; Goel, A., Synthesis and docking studies on styryl chromones exhibiting cytotoxicity in human breast cancer cell line. Bioorg. Med. Chem. Lett. 2010, 20, 4945-4950.
15. Alves, C. N.; Pinheiro, J. C.; Camargo, A. J.; de Souza, A. J.; Carvalho, R. B.; da Silva, A. B. F., A quantum chemical and statistical study of flavonoid compounds with anti-HIV activity. J. Mol. Struct. (Theochem) 1999, 491, 123-131.
16. Ungwitayatorn, H.; Samee, W.; Pimthon, J., 3D-QSAR studies on chromone derivatives as HIV-1 protease inhibitors. J. Mol. Struct. 2004, 689, 99-106.
17. Göker, H.; Ozden, S.; Yildiz, S.; Boykin, D. W., Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines. Eur. J. Med. Chem. 2005, 40, 1062-1069.
18. Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. From 2000 to Mid-2010: A fruitful decade for the synthesis of pyrazoles. Chem. Rev. 2011, 111, 6984–7034.
19. Ansari, A.; Ali, A.; Asif, M. biologically active pyrazole derivatives. New J. Chem. 2017, 41, 16–41.
20. Steinbach, G.; Lynch, P.M.; Robin, K.S.P.; Wallace, M.H.; Hawk, E.; Gordon, G.B.;Wakabayashi, N.; Saunders, B.; Shen, Y.; Fujimura, T.; Su, L.-K.; Levin, A.B. The effect of celecoxib, a cyclooxygenase-2 inhibitor, in familial adenomatous polyposis. N. Engl. J. Med. 2000, 342, 1946–1952.
21. Uslaner, J.M.; Parmentier-Batteur, S.; Flick, R.B.; Surles, N.O.; Lam, J.S.; McNaughton, C.H. Dose-dependent effect of CDPPB, the mGluR5 positive allosteric modulator, on recognition memory is associated with GluR1 and CREB phosphorylation in the prefrontal cortex and hippocampus. Neuropharmacology 2009, 57, 531–538.
22. Friedrich, G.; Rose, T.; Rissler, K. Determination of lonazolac and its hydroxy and O-sulfated metabolites by on-line sample preparation liquid chromatography with fluorescence detection. J. Chromatogr. B 2002, 766, 295–305.
23. Hampp, C.; Hartzema, A.G.; Kauf, T.L. Cost-utility analysis of rimonabant in the treatment of obesity. Value Health 2008, 11, 389–399.
24. Spitz, I.; Novis, B.; Ebert, R.; Trestian, S.; LeRoith, D.; Creutzfeld,W. Betazole-induced GIP secretion is not mediated by gastric HCl. Metabolism 1982, 31, 380–382.
25. Luttinger, D.; Hlasta, D.J. Antidepressant Agents. Annu. Rep. Med. Chem. 1987, 22, 21–30.
26. Tsutomu, K.; Toshitaka, N. Effects of 1,3-diphenyl-5-(2-dimethylaminopropionamide)-pyrazole [difenamizole] on a conditioned avoidance response. Neuropharmacology 1978, 17, 249–256.
27. García-Lozano, J.; Server-Carrió, J.; Escrivà, E.; Folgado, J.-V.; Molla, C.; Lezama, L. X-ray crystal structure and electronic properties of chlorobis (mepirizole) copper (II) tetrafluoroborate (mepirizole -4-methoxy-2-(5-methoxy-3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine). Polyhedron 1997, 16, 939–944.
28. Chemistry Letters, 2001, 30 (2), 110-111.
29. Satishkumar D. Tala , Hitendra Joshi , Bhavesh L. Dodiya ,Synthesis and biological study of some new chalcone and pyrazole derivatives; Indian Journal of Chemistry ;Vol. 52B, June 2013, pp 807-809.
30. R. Ahmad, A. M. Ali, D. A. Israf, N. H. Ismail, K. Shaari, and N. H. Lajis, “Antioxidant, radical-scavenging, anti-inflammatory, cytotoxic and antibacterial activities of methanolic extracts of
some Hedyotis species,” Life Sciences, vol. 76, no. 17, pp. 1953– 1964, 2005. 31. Mohammed, M. K., Mohammad, M. R., Jabir, M. S., and Ahmed, D. S. (2020). Functionalization, characterization, and antibacterial activity of single wall and multi wall carbon nanotubes. In IOP Conference Series: Materials Science and Engineering (Vol. 757, No. 1, p. 012028). IOP Publishing. 32. Ibraheem, S. A., Kadhem, H. A., Hadeethi, S. A., Jabir, M. S., Grigore, R., Popa, M., & Florin, M. D. (2019). Effects of silver nanoparticles on nosocomial Pseudomonas aeruginosa strains–an alternative approach for antimicrobial therapy. Romanian Biotechnological Letters, 24(2), 286-293.
33. Khashan, K. S., Jabir, M. S., & Abdulameer, F. A. (2018). Carbon Nanoparticles decorated with cupric oxide Nanoparticles prepared by laser ablation in liquid as an antibacterial therapeutic agent. Materials Research Express, 5(3), 035003. 34. Jabir, M. S., Nayef, U. M., Jawad, K. H., Taqi, Z. J., and Ahmed, N. R. (2018). Porous silicon nanoparticles prepared via an improved method: a developing strategy for a successful antimicrobial agent against Escherichia coli and Staphylococcus aureus. In IOP Conference Series: Materials Science and Engineering (Vol. 454, No. 1, p. 012077). IOP Publishing. 35. Jabir, M. S., Sulaiman, G. M., Taqi, Z. J., and Li, D. (2018). Iraqi propolis increases degradation of IL-1β and NLRC4 by autophagy following Pseudomonas aeruginosa infection. Microbes and infection, 20(2), 89-100. 36. Kadhem, H. A., Ibraheem, S. A., Jabir, M. S., and Kadhim, A. A. (2019). Zainab Jihad taqi, and mihailescu dan florin, zinc oxide nanoparticles induce apoptosis in human breast cancer cells via caspase-8 and P53 pathway. Nano Biomed. Eng, 11(1), 35-43.
37. Al-Majedy, Y.K., Ibraheem, H.H., Shamel, S., Al-Amiery, A.A.,Synthesis and Study of the fluorescent properties of 4-hydroxy-coumarin derivatives,Journal of Physics: Conference Seriesthis link is disabled, 2021, 1795(1), 012001
38. Ibraheem, H.H., Mohammed, M.M., Al-Majedy, Y.K., Synthesis and Quantum Chemical Study of Novel Pyridine Derivative Derived from N-Substituted Coumarin,Journal of Physics: Conference Seriesthis link is disabled, 2021, 1795(1), 012024.
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Jun 4, 2023
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Zahraa Haithem, Yasameen K. Al-Majedy, & Majid S.Jabir. (2023). Design and Synthesis of Chalcone and Chromone Derivatives as Antimicrobial Agents. Journal of Population Therapeutics and Clinical Pharmacology, 30(13), 324–329. https://doi.org/10.47750/jptcp.2023.30.13.032
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