Flavonoids as vasorelaxant agents: Synthesis, biological evaluation and quantitative structure activities relationship (QSAR) studies

Molecules

Volumn 16, Issue 10, 2011, Pages 8257-8272

  Dong, Xiaowu ^a   Wang, Yanming ^a   Liu, Tao ^a   Wu, Peng ^a   Gao, Jiadi ^a   Xu, Jianchao ^a   Yang, Bo ^a   Hu, Yongzhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

ERM MLR; Flavonoids; Molecular descriptors; QSAR; Vasorelaxant agents

Indexed keywords

2 (2 DIETHYLAMINO) ETHOXYCHALCONE; 2-(2-DIETHYLAMINO)-ETHOXYCHALCONE; CHALCONE DERIVATIVE; ETHYLAMINE; FLAVONOID; VASODILATOR AGENT;

ANIMAL; AORTA; ARTICLE; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; METABOLISM; ORGAN CULTURE TECHNIQUE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SYNTHESIS;

ANIMALS; AORTA; CELLS, CULTURED; CHALCONES; ETHYLAMINES; FLAVONOIDS; MOLECULAR STRUCTURE; ORGAN CULTURE TECHNIQUES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; VASODILATOR AGENTS;

EID: 80054882026     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16108257     Document Type: Article

References (24)

1. Grassi, D.; Desideri, G.; Croce, G.; Tiberti, S.; Aggio, A.; Ferri, C. Flavonoids, vascular function and cardiovascular protection. Curr. Pharm. Design 2009, 10, 1072-1084.
2. Harborne, J. B.; Williams, C. A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55, 481-504.
3. Bravo, L. Polyphenols: Chemistry, dietary sources, metabolism, and nutritional significance. Nutr. Rev. 1986, 56, 317-333.
4. García-Lafuente, A.; Guillamán, E.; Villares, A.; Rostagno, M. A.; Martínez, J. A. Flavonoids as anti-inflammatory agents: Implications in cancer and cardiovascular disease. Inflamm. Res. 2009, 58, 537-552.
5. Tripoli, E.; Guardia, M. L.; Giammanco, S.; Majo, D. D.; Giammanco, M. Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review. Food Chem. 2007, 104, 466-479. (Pubitemid 46661050)
6. Stoclet, J. C.; Chataigneau, T.; Ndiaye, M.; Oak, M. H.; El Bedoui, J.; Chataigneau, M.; Schini-Kerth, V. B. Vascular protection by dietary polyphenols. Eur. J. Pharmacol. 2004, 500, 299-313. (Pubitemid 39304017)
7. Kris-Etherton, P. M.; Keen, C. L. Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr. Opin. Lipidol. 2002, 13, 41-49. (Pubitemid 34174628)
8. + channels via cyclic nucleotide-dependent protein kinases in mesenteric artery. Phytomedicine 2010, 17, 760-770.
9. Xu, Y. C.; Leung, S. W. S.; Yeung, D. K. Y.; Hu, L. H.; Chen, G. H.; Che, C. M.; Man, Y. K. R. Structure-activity relationships of flavonoids for vascular relaxation in porcine coronary artery Phytochemistry 2007, 68, 1179-1188. (Pubitemid 46528458)
10. Benavente-Garcia, O.; Castillo, J. Update on uses and properties of citrus flavonoids: New findings in anticancer, cardiovascular, and anti-inflammatory activity. J. Agric. Food Chem. 2008, 56, 6185-6205.
11. Ma, X.; Li, Y.; Gao, Q.; Ye, Z.; Lu, X.; Wang, H.; Jiang, H.; Bruce, I. C.; Xia, Q. Inhibition of superoxide anion-mediated impairment of endothelium by treatment with luteolin and apigenin in rat mesenteric artery. Life Sci. 2008, 83, 110-117.
12. Woodman, O. L.; Meeker, W. F.; Boujaoude, M. Vasorelaxant and antioxidant activity of flavonols and flavones: Structure-activity relationships. J. Cardiovasc. Pharmacol. 2005, 46, 302-309. (Pubitemid 41262832)
13. Chen, Z.; Hu, Y.; Wu, H.; Jiang, H. Synthesis and biological evaluation of flavonoids as vasorelaxant agents. Bioorg. Med. Chem. Lett. 2004, 14, 3949-3952. (Pubitemid 38844402)
14. Dong, X. Liu, T.; Yan, J.; Wu, P.; Chen, J.; Hu, Y. Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents. Bioorg. Med. Chem. 2009, 17, 716-726.
15. Dong, X.; Chen, J.; Jiang, C.; Liu, T.; Hu, Y. Design, synthesis, and biological evaluation of prenylated chalcones as vasorelaxant agents. Arch. Pharm. 2009, 342, 428-432.
16. Dong, X.; Qi, L.; Jiang, C.; Chen, J.; Wei, E.; Hu, Y. Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents. Bioorg. Med. Chem. Lett. 2009, 19, 3196-3198.
17. Dong, X.; Fan, Y.; Yu, L.; Hu, Y. Synthesis of four natural prenylflavonoids and their estrogen-like activities. Arch. Pharm. 2007, 340, 372-376. (Pubitemid 47121194)
18. Qian, L.; Wang, H.; Qiu, W.; Huang, H.; Bruce, I. C.; Xia, Q. Interleukin-2 protects against endothelial dysfunction induced by high glucose levels in rats. Vascul. Pharmacol. 2006, 45, 374-382. (Pubitemid 44765302)
19. Dong, X.; Liu, Y.; Yan, J.; Jiang, C.; Chen, J.; Liu, T.; Hu, Y. Identification of SVM-based classification model, synthesis and evaluation of prenylated flavonoids as vasorelaxant agents. Bioorg. Med. Chem. 2008, 16, 8151-8160.
20. Talete srl. DRAGON for Windows software for molecular descriptor calculation. Available online: http://talete.mi.it. (accessed on 14 September 2011).
21. Mercader, A. G.; Duchowicz, P. R.; Fernández, F. M.; Castro, E. A. Modified and enhanced replacement method for the selection of molecular descriptors in QSAR and QSPR theories. Chemom. Intell. Lab. Syst. 2008, 92, 138-144.
22. Duchowicz, P. R.; Castro, E. A.; Fernández, F. M. Alternative algorithm for the search of an optimal set of descriptors in QSAR - QSPR studies. MATCH Commun. Math. Comput. Chem. 2006, 55, 179-192.
23. Duchowicz, P. R.; Fernández, M.; Caballero, J.; Castro, E. A.; Fernández, F. M. QSAR for non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg. Med. Chem. 2006, 14, 5876-5889. (Pubitemid 44096998)
24. Gong, G. Cross-validation, the jackknife and the bootstrap excess error estimation in forward regression logistic regression, J. Am. Stat. Assoc. 1986, 81, 108-113.