Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants

Biochimie

Volumn 92, Issue 9, 2010, Pages 1138-1146

  Kancheva, Vessela D ^a   Boranova, Petya V ^a   Nechev, Jordan T ^a   Manolov, Ilia I ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

4 hydroxy bis coumarins; Antioxidants; Binary mixtures; Lipid oxidation

Indexed keywords

3,3' [(3,4 DIHYDROXY PHENYL) METHYLENE] BIS (4 HYDROXY CHROMEN 2 ONE); 3,3' [(3,4 DIMETHOXYPHENYL) METHYLENE] BIS (4 HYDROXY CHROMEN 2 ONE); 3,3' [(3,4,5 TRIMETHOXYPHENYL) METHYLENE] BIS (4 HYDROXY CHROMEN 2 ONE); 3,3' [(4 HYDROXY 3 METHOXY 5 NITROPHENYL) METHYLENE] BIS (4 HYDROXY CHROMEN 2 ONE); 3,3' [(4 HYDROXY 3,5 DIMETHOXY PHENYL) METHYLENE] BIS(4 HYDROXY CHROMEN 2 ONE); 4 HYDROXY BIS COUMARIN; 4 HYDROXY CHROMEN 2 ONE; ALPHA TOCOPHEROL; ANTIOXIDANT; CAFFEIC ACID; CINNAMIC ACID; COUMARIN DERIVATIVE; FERULIC ACID; PARA COUMARIC ACID; SCAVENGER; SINAPIC ACID; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG CROSS REACTIVITY; DRUG EFFICACY; DRUG OXIDATION; DRUG POTENTIATION; DRUG STABILITY; LIPID PEROXIDATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

ANTIOXIDANTS; CHROMATOGRAPHY, THIN LAYER; COUMARINS; FREE RADICAL SCAVENGERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955845633     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2010.02.033     Document Type: Article

References (29)

1. Zaneva O., Manolov I., Danchev N. Toxicological and Pharmacological Investigations of Newly Synthesized Derivatives of 4-hydroxycoumarin 2005, vol. LII. Pharmacia, Sofia, 1-2 85-89.
2. Manolov I., Maichle-Moessmer C., Nicolova I., Danchev N. Synthesis and anticoagulant activities of Substituted 2,4-Diketochromans, biscoumarins and chromanocoumarins. Arch. Pharm. Chem. Life Sci. 2006, 339:319-326.
3. Manolov I., Maichle-Moessmer C., Danchev N. Synthesis, structure, toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 2006, 41:882-890.
4. Chavasiri W., Deesamer S., Kokpol U., Thipnoisanga C., Wattanasereekul S., Zungsontiporn S. Searching of new agrochemicals part 1. Structure-activity relationship study of dicoumarols as weed growth inhibitors against Mimosa pigra Linn. Thai J. Agric. Sci. 2001, 34:81-89.
5. Khan K.M., Iqbal S., Lodhi M.A., Maharvi G.M., Zia-Ullah, Choudhary M.I., Atta-ur-Rahman, Perveen S. Biscoumarin: new class of urease inhibitors; economical synthesis and activity. Bioorg. Med. Chem. 2004, 12:1963-1968.
6. Mitra A.K., De A., Karchaudhuri N., Misra S.K., Mukhopadhyay A.K. Carbon-13 NMR chemical shifts of some dicoumarols and benzopyranodicoumarins. J. Indian Chem. Soc. 1998, 75:526-528.
7. St.Stanchev C., Maichle-Mössmer I. Manolov synthesis, structure and acid-base behavior of some 4-hydroxycoumarin derivatives. Z. Naturforch 2007, B 62b(5):737-741.
8. Grussner A. Derivatives of dicoumarol and their anticoagulant action. Jubilee Vol Emil Barell 1946, 238-252.
9. Desnoyers P., Binovic K. 4-Hydroxycoumarin derivatives, new antivitamin K compounds. Therapie 1967, 22(1):207-218.
10. Perola E., Xu K., Kollmeyer T.M., Kauffman S.H., Prendergast F.G., Pang Y.-P. Successful virtual screening of a chemical database for farnesyltransferase inhibitor leads. J. Med. Chem. 2000, 43:401-408.
11. Griffith R., Chanphen R., Leach S.P., Keller P.A. New antimalarial compounds from database searching. Bioorg. Med. Chem. Lett. 2002, 12:539-542.
12. Keller P.A., Birch C., Leach S.P., Tyssen D., Griffith R. Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor. J. Mol. Graphics & Modelling 2003, 21:365-373.
13. Khan K.M., Iqbal S., Lodhi M.A., Maharvi G.M., Perveen S., Choudhary M.I., Atta-Ur-Rahman, Zahid Z.H., Supuran C.T. Synthesis and urease enzyme inhibitory effects of some dicoumarols. J. Enzyme Inhib. Med. Chem. 2004, 19:367-371.
14. Prabhakar K.R., Veerapur V.P., Bansal P., et al. Identification and evaluation of antioxidant, analgestic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized. Bioorg. Med. Chem. 2006, 14:7113-7120.
15. Yordanov N.D. Is our knowledge about the chemical and the physical properties of DPPH enough to consider it as a primary standard for quantitative EPR spectrometry. Appl. Magn. Reson 1996, 10:339-350.
16. Popov A., Yanishlieva N., Slavcheva J. Methode zum Nachweis von Antioxidanten in Methyloleat fur kinetische Untersuchungen. Compt. Rend. Acad. Bulg. Sci. 1968, 21:443-446.
17. Christie W.W. Lipid Analysis 2003, The Oily Press, Bridgwater (England), p. 208.
18. Yanishlieva N., Popov A. Uber einige Eigentumlichkeit in der Kinetik zu Beginn der Autoxydation von Estern ungesattigter Fettsauren. 3. Mitt. Inhibierte Autoxydation. Die Nahrung 1971, 15:671-681.
19. Kancheva V. Phenolic antioxidants-antiradical and antioxidant activity. Comparative study. Eur. J. Lipid Sci. Technol 2009, 111:1072-1089.
20. Denisov E.T., Afanas'ev I.B. Oxidation and Antioxidants in Organic Chemistry and Biology 2005, CRC Press, Boca Ration, 1024pp.
21. Doerffel K. Statistics in the Analytical Chemistry 1994, 251 pp, Mir, Moscow, (in Russian).
22. V. Kancheva, L. Saso, P. Boranova, et al. Structure-Antioxidant Activity Relationship of Some Dihydroxy Coumarins; 5th Indo-Italian Workshop: " Chemistry and Biology of Antioxidants" , 5-9 July 2009, Rome, Italy, 24.
23. Nishida J., Kawabata J. DPPH radical scavenging reaction of hydroxy- and Methoxychalcones. Biosci. Biotechnol. Biochem. 2006, 70:193-202.
24. Nenadis N., Tsimidou M. Observations of the estimation of scavenging activity of phenolic compounds using rapid 1,1-Diphenyl-2-picrylhudrazyl (DPPH) Tests. JAOCS 2002, 79:1191-1195.
25. Torres R., Faini F., Modak B., Urbina F., Labbe C., Guerrero J. Antioxidant activity of coumarins and flavonols from the resinous exudates of Haplopappus multifolius. Phytochemistry 2006, 67:984-987.
26. Kasaikina O.T., Kortenska V.D., Yanishlieva N.V. Effects of chain transfer and recombination/disproportionation of inhibitor radicals on inhibited oxidation of lipids. Russ. Chem. Bul. 1996, 48:1891.
27. Denisov E.T., Denisova T.G. Handbook of Antioxidants. Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions 2001, CRS Press, New York, Washington D.C. second ed.
28. Kancheva V.D., Dinchev D., Tsimidou M., Kostova I., Nenadis N. Antioxidant properties of Tribulus Terrestris from Bulgaria and radical scavenging activity of its flavonoid Components. Riv. Ital. delle Sost. Grasse 2007, 84:10-19.
29. Vermerris W., Nickolson R. Phenolic Compound Biochemistry 2006, Springer, Dordrecht, The Netherlands, 48-61p.