Synthesis and Pharmacological Evaluation of 2′-Hydroxychalcones and Flavones as Inhibitors of Inflammatory Mediators Generation

Journal of Medicinal Chemistry

Volumn 38, Issue 14, 1995, Pages 2794-2797

  Ballesteros, J F ^a   Sanz, M J ^a   Ubeda, A ^a   Miranda, M A ^b   Iborra, S ^b   Paya M ^a   Alcaraz, M J ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2' HYDROXY 3',4',3,4 TETRAMETHOXYCHALCONE; 2' HYDROXY 3,4 DIMETHOXY 3',4' DIMETHYLCHALCONE; 3',4',7,8 TETRAMETHOXYFLAVONE; ANTIINFLAMMATORY AGENT; CHALCONE DERIVATIVE; ELASTASE; FLAVONE DERIVATIVE; LACTATE DEHYDROGENASE; LEUKOTRIENE B4; PHOSPHOLIPASE A2; SCAVENGER; SUPEROXIDE; THROMBOXANE B2; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DEGRANULATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN TISSUE; LIPID PEROXIDATION; LIVER MICROSOME; MOUSE; NEUTROPHIL; NONHUMAN; RAT; TOPICAL DRUG ADMINISTRATION;

ANIMAL; CELL DEGRANULATION; CHALCONE; EICOSANOIDS; FLAVONES; FREE RADICAL SCAVENGERS; HUMAN; INFLAMMATION MEDIATORS; LIPID PEROXIDATION; MICE; NEUTROPHILS; PANCREATIC ELASTASE; PHOSPHOLIPASES A; SUPPORT, NON-U.S. GOV'T; SYNOVIAL FLUID;

EID: 0029047744     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00014a032     Document Type: Article

References (30)

1. 4-induced microsomal lipid peroxidation. Experientia 1991, 47, 195-199.
2. Mora, A.; Paya, M.; Rios, J. L.; Alcaraz, M. J. Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of non-enzymic lipid peroxidation. Biochem. Pharmacol. 1990, 40, 793-797.
3. Huguet, A. I.; Manez, S.; Alcaraz, M. J. Superoxide scavenging properties of flavonoids in a non-enzymic system. Z. Naturforsch. 1990, 45C, 19-24.
4. Rios, J. L.; Manez, S.; Paya, M.; Alcaraz, M. J. Antioxidant activity of flavonoids from Sideritis javalambrensis. Phytochemistry 1992, 31, 1947-1950.
5. Sanz, M. J.; Ferrándiz, M. L.; Cejudo, M.; Terencio, M. C.; Gil, B.; Bustos, G.; Ubeda, A.; Gunasegaran, R.; Alcaraz, M. J. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica 1994, 24, 689-699.
6. Alcaraz, M. J.; Hoult, J. R. S. Effects of hypolaetin-8-glucoside and related flavonoids on soybean lipoxygenase and snake venom phospholipase A2. Arch. Int. Pharmacodyn. 1985, 278, 4-12.
7. Villar, A.; Gasco, M. A.; Alcaraz, M. J. Some aspects of the inhibitory activity of hypolaetin-8-glucoside in acute inflammation. J. Pharm. Pharmacol. 1987, 39, 502-507.
8. Moroney, M. A.; Alcaraz, M. J.; Forder, R. A.; Carey, F.; Hoult, J. R. S. Selectivity of neutrophil 5-lipoxygenase and cyclooxygenase inhibition by an antiinflammatory flavonoid glycoside and related aglycone flavonoids. J. Pharm. Pharmacol. 1988, 40, 787-792.
9. Ferrandiz, M. L.; Alcaraz, M. J. Antiinflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents Actions 1991, 32, 283-286.
10. 2 and inflammatory responses in mice. Life Sci. 1994, 54, 333-338.
11. Kurzer, F.; Doureghi-Zadek, K. Advances in the chemistry of carbodiimides. Chem. Rev. 1967, 107-152.
12. Williams, A.; Ibrahim, I. T. Carbodiimide chemistry: recent advances. Chem. Rev. 1981, 589-636.
13. Haslam, E. Recent developments in methods for esterification and protection of the carboxyl group. Tetrahedron 1980, 36, 2409-2433.
14. Garcia, H.; Iborra, S.; Miranda, M. A.; Primo, J. 6-Endo-Dig versus 5-Exo-dig ring clousure in o-hydroxyaryl phenylethynyl ketones. A new approach to the synthesis of flavones and aurones. J. Org. Chem. 1986, 51, 4432-4436.
15. Ramakrishnan, V. T.; Kagan, J. The photochemical synthesis of 2′-hydroxychalcones from phenyl cinnamates. J. Org. Chem. 1970, 35, 2901-2904.
16. Obara, H.; Takahashi, H. The photochemical Fries rearrangement of phenyl cinnamates. Bull. Chem. Soc. Jpn. 1967, 40, 1012.
17. Obara, H.; Takahashi, H.; Hirano, H. The photo-Fries rearrangement of hydroxyphenyl cinnamates. Bull. Chem. Soc. Jpn. 1969, 42, 560-561.
18. Singh, A. K.; Ranghvraman, T. S. Photorearrangement of phenyl cinnamate under micellar environment. Tetrahedron Lett. 1985, 26, 4125-4128.
19. Garcia, H.; Iborra, S.; Miranda, M. A.; Primo, J. Application of the photo-Fries rearrangement of aryl dihydrocinnamates to the synthesis of flavonoids. Heterocycles 1985, 23, 1983-1989.
20. Makrandi, J. K.; Seema, P. An efficient procedure for cyclization of 2′-hydroxychalcones into flavones. Chem. Ind. 1989, 607-608.
21. Bors, W.; Saran, M. Radical scavenging by flavonoid antioxidants. Free Radical Res. Commun. 1987, 2, 289-294.
22. Cotelle, N.; Bernier, J. L.; Henichart, J. P.; Catteau, J. P.; Gaydou, E.; Wallet, J. C. Scavenger and antioxidant properties of ten synthetic flavones. Free Radical Biol. Med. 1992, 13, 211-219.
23. 2. Biochim. Biophys. Acta 1993, 117, 217-231.
24. Ubeda, A.; Montesinos, C.; Paya, M.; Terencio, M. C.; Alcaraz, M. J. Antioxidant action of benzylisoquinoline alkaloids. Free Radical Res. Commun. 1993, 18, 167-175.
25. Halliwell, B. How to characterize a biological antioxidant. Free Radical Res. Commun. 1990, 9, 1-32.
26. Ubeda, A.; Montesinos, C.; Paya, M.; Alcaraz, M. J. Iron reducing and free radical scavenging properties of apomorphine and some related benzylisoquinolines. Free Radical Biol. Med. 1993, 15, 159-167.
27. 2 associated with rabbit polymorphonuclear leukocyte granules. J. Lipid Res. 1974, 15, 380-388.
28. Ferrandiz, M. L.; Sanz, M. J.; Bustos, G.; Paya, M.; Alcaraz, M. J.; De Rosa, S. Avarol and avarone, two new antiinflammatory agents of marine origin. Eur. J. Pharmacol. 1994, 253, 75-82.
29. Bergmeyer, H. U.; Bernt, E. Lactate dehydrogenase: UV assay with pyruvate and NADH. In Methods of enzymatic analysis; Bergmeyer, H. U., Ed.; Academic Press: New York, 1974; pp 574-577.
30. Carlson, R. P.; O’Neill-Davis, L.; Chang, J.; Lewis, A. J. Modulation of mouse ear edema by cyclooxygenase and lipoxygenase inhibitors and other pharmacologic agents. Agents Actions 1985, 17, 197-204.