Synthesis of some Heterocyclic compounds bearing Coumarin nucleus and their Anti-inflammatory activity
DOI:
https://doi.org/10.24297/jac.v12i5.5180Keywords:
6-amino-4-methylcoumarin, Multi-component reactions, Microwave irradiation assistant, Anti-inflammatory Activity.Abstract
Starting from 6-amino-4-methyl-2H-chromen-2-one 1, a series of some new heterocyclic compounds (2-14) incorporating coumarin moiety was synthesized and assessed for their anti-inflammatory activity using the carrageenan-induced hind paw edema method. The tested coumarin derivatives reduce the edema volume and serum levels of the pro inflammatory cytokines, IL-6 and TNF-α, and have effects on promoting production of anti-inflammatory cytokine, IL-10.Downloads
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References
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2. Kazuo, M.; Kazuya, O.; Hironobu, H. Mukai, K.; Okabe, K.; Hosose, H. ''Synthesis and stopped-flow investigation of antioxidant activity of tocopherols. Finding of new tocopherol derivatives having the highest antioxidant activity among phenolic antioxidant''. J. Org. Chem., 1989, 54, 557-560 .
3. Kostova, I. ''Synthetic and natural coumarins as cytotoxic Agents''. Curr. Med. Chem., 2005, 5, 29-46.
4. Yourick, J. J.; Bronaugh, R. L. ''Percutaneous absorption and mechanism of coumarin in human and rat skin''. J. Appl. Toxicol., 1997, 17, 153-158
5. O’Kennedy, R.; Thornes, R. D. '' Coumarins: Biology, Applications, and Mode of Action''. John Wiley&Sons, New York, 1997.
6. Nielson, B. E. ''Heywood in the Biology and Chemistry of the Umbelliferae'', Academic Press, London, 1971.
7. Murray, R. D. H.; Mendez, J.; Brown, S. A. ''The Natural Coumarins, Occurrence, Chemistry and Biochemistry''. John Wiely&Sons, New York, 1982.
8. Yamazaki, H.; Tanaka, M.; Shimada, T. ''Highly sensitive high-performance liquid chromatographic assay for coumarin 7-hydroxylation O-deethylation by human liver cytochrome P450 enzymes''. J. Chromatoger. B., 1999, 721, 13-19.
9. Izquierfo, M. E. F.; Granados, J. Q.; Mir, V. M.; Martinez, M. C. L. ''Comparison of methods for determining coumarins in distilled beverages''. Food Chem., 2000, 70, 251-258.
10. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. ''Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds''. Chem. Rev., 2004, 104, 3059-3078.
11. Di Braccio, M.; Grossi, G.; Roma, G.; Marzano, C.; Bacccichetti, F.; Simonato, M.; Bordin, F. ''Pyran derivatives: Part XXI. Antiproliferative and cytotoxic properties of novel N-substituted 4-aminocoumarins, their benzo-fused derivatives, and some related 2-aminochromones'' .F. II Farmaco., 2003, 58, 1083.
12. Roma, G.; Di Braccio, M.; Carrieri, A.; Grossi, G.; Leoncini, G.; Signorello, M. G.; Carotti, A. ''Coumarin, chromone, and 4(3H)-pyrimidinone novel bicyclic and tricyclic derivatives as antiplatelet agents: synthesis, biological evaluation, and comparative molecular field analysis''. Bioorg Med Chem., 2003, 11, 123. 13. El-Saghier, A. M. M.; Naili, M. B.; Rammash, B. Kh.; Saleh, N. A.; Kreddanc, K. M. '' Synthesis and antibacterial activity of some new fused chromenes'' Arkivoc., 2007, (xvi), 83-91.
14. Kokotos, G.; Theodorou, V.; Tzougraki Dieter, C.; Deforce, L. D.; Van den Eeckhout, E. G. Bioorg. Med. Chem. Lett., 1998, 7, 2165.
15. Jarrahpour, A. A.; Jalbout, A. F.; Rezaei, S.; and Trzaskowski, B. Malbank., 2006, M455.
16. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc., 2002, 124, 6626.
17. Jarrahpour, A. A.; Shekarriz, M.; Taslimi, A. ''Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams''. Molecules. 2004, 9, 29-38.
18. Chohan, Z. H.; Arif, M.; Shafiq, Z.; Yaqub, M.; Supuran, C. T. J. Enzyme Inhib Med Chem., 2006, 21(1), 95-103.
19. Ren, S.; Wang, R.; Komatsu, K.; Bonaz-Krause, P.; Zyrianov, Y.; McKenna, C. E.; Cipke, C.; Tokes, Z. A.; Lien, E. J. ''Synthesis, Biological Evaluation, and Quantitative Structure−Activity Relationship Analysis of New Schiff Bases of Hydroxysemicarbazide as Potential Antitumor Agents'' . J Med Chem., 2002, 45(2), 410-419.
20. Al-Haiza, M. A.; Mostafa, M. S.; El-Kady, M. Y. "Preparation of Some New Coumarin Derivatives with Biological Activity". Sci. J. of king Faisal University (Basic and Applied Science)., 2005, 6(1), 1426.
21. Haitham, D. H." Synthesis and Characterization of New Seven-Membered Heterocyclic Compounds from Reaction of New Schiff-Bases with Maleic and Phthalic anhydrides". National J. Chem., 2011, 41, 77-89.
22. Abdul Amir H. K.; Ahmed A. Al-Amiery.; Ahmed Y. M.; Abu Bakar M. "The Antioxidant Activity of New Coumarin Derivatives ".Int J. Mol Sci., 2011, 12, 5747-5761.
23. Mukul Sharma, M.; Manohar, S.; Rawat, S. ''W. Lewis Acid Catalyzed Synthesis of 1-Aryl-1,2-dihydro-naphtho[1,2-e][1,3]oxazin-3-ones under Solvent Free Conditions''. J. Heterocyclic Chem., 2012, 49(3), 589-595.
24. Zhang, Z.; Wang, S.; Zhang, G. ''Facile synthesis of 5-aryl-1-[(arylamino) methyl] - 1, 3, 5-triazinane-2-thiones''. J. Heterocyclic Chem., 2012, 49(2), 433-437.
25. Mashkouri, S.; Naimi-Jamala, M. R.; Sharifi, A. ''Solvent-Free Synthesis of 2-Amino-4H-Chromenes Catalyzed by Sodium Carbonate''. 12th International Electronic Conference on synthetic organic chemistry., 2008, (Ecsoc-12), 1-30.
26. Bi-HuiXu, Man-Su Tu.; Yin-Ping , Liu.; Jiang ,Bo.; Xing-Hang, Wang.; and Shu-Jiang ,Tu. '' Microwave-Assisted Three-Component Reactions Leading to Pyrano-Fused Pyrazolo[3,4-b]pyridines''. J. Het Chem., 2014, 51(6), 1591–1594.
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Published
2016-05-12
How to Cite
T. A. Dawoud1, N., F.Abdel-Ghaffar, N., Abdl-gali, M. M., Soliman, F. M. A., & Zaki, H. M. (2016). Synthesis of some Heterocyclic compounds bearing Coumarin nucleus and their Anti-inflammatory activity. JOURNAL OF ADVANCES IN CHEMISTRY, 12(5), 4442–4452. https://doi.org/10.24297/jac.v12i5.5180
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