Synthesis and biological evaluation of novel series of chalcone derivatives as inhibitors of cyclooxygenase and LPS-induced TNF-α with potent antioxidant properties

Medicinal Chemistry Research

Volumn 21, Issue 9, 2012, Pages 2292-2299

  Bandgar, Babasaheb P ^a,b   Hote, Baliram S ^a   Dhole, Nagesh A ^a   Gacche, Rajesh N ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

^b SOLAPUR UNIVERSITY   (India)

Author keywords

Antioxidant; COX 1; COX 2; Enzyme inhibition; TNF ; WBCs

Indexed keywords

1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (1H PYRROL 3 YL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (2,4 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (2,5 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (3 BROMOPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (3 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (3 NITROPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (4 CHLORO 3 NITROPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (4 CHLOROPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (PYRIDINE 3 YL)PROP 2 EN 1 ONE; 3 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (2 CHLOROPHENYL)PROP 2 EN 1 ONE; 3 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (2 FLUOROPHENYL)PROP 2 EN 1 ONE; 3 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 (2,4 DICHLOROPHENYL)PROP 2 EN 1 ONE; 3 (3 BROMO 2 HYDROXYL 4,6 DIMETHOXYPHENYL) 3 [3 (TRIFLUOROMETHYL)PHENYL]PROP 2 EN 1 ONE; 3 [3 (3 BROMO 2 HYDROXY 4,6 DIMETHOXYPHENYL) 3 OXOPROP 1 ENYL]BENZONITRILE; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; BETA GLUCURONIDASE; CHALCONE DERIVATIVE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; TRYPSIN; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL;

EID: 84866367447     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9746-6     Document Type: Article

References (34)

1. Ahluwalia VK (2005) Intermediates for organic synthesis. I. K. International Publisher, New Delhi
2. Bandgar BP, Patil SA, Gacche RN, Korbad BL, Hote BS, Kinkar SN, Jalde SS (2010) Synthesis and biological evaluation of nitrogencontaining chalcones as possible anti-inflammatory and antioxidant agents. Bioorg Med Chem Lett 20:730-733
3. Bartolome B, Nunez V, Monagas M, Gomez-Cordoves C (2004) In vitro antioxidant activity of red grape skins. Eur Food Res Technol 218:173-177 (Pubitemid 40890189)
4. Bilfinger TV, George BS (2002) The role of protease inhibition with emphasis on the effects of inflammation and vascular immune phenomena. Curr Pharm Design 8:125-133
5. Bois F, Beney C, Boumendijel A, Mariotte AM, Conseil G, DiPietro A (1998) Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance. J Med Chem 41:4161-4164 (Pubitemid 28483491)
6. Cechinel-Filho VF, Vaz ZR, Zunino L, Calixto JB, Yunes RA (1996) Synthesis of xanthoxyline derivatives with antinociceptive and antioedematogenic activities. Eur J Med Chem 31:833-839 (Pubitemid 26341449)
7. Dhar DN (1981) The chemistry of chalcones and related compounds. Wiley, New York
8. Di Carlo G, Mascolo N, Izzo AA, Capasso F (1999) Flavonoids: old and new aspects of a class natural therapeutic drugs. Life Sci 65:337-353 (Pubitemid 29325278)
9. Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ, McGown AT, Rennison D (1998) Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 8:1051-1056 (Pubitemid 28216282)
10. Furman C, Lebeau J, Fruchart J-C, Bernier J-L, Duriez P, Cotelle N, Teissier E (2001) Di-tert-butylhydroxylated flavonoids protect endothelial cells against oxidized LDL-induced cytotoxicity. J Biochem Mol Toxicol 15:270-278 (Pubitemid 33100366)
11. Gacche RN, Dhole NA (2006) Antioxidant and possible antiinflammatory potential of selected medicinal plants prescribed in Indian traditional system of medicine. Pharm Biol 44:389-395 (Pubitemid 43995611)
12. Gacche R, Khsirsagar M, Kamble S, Bandgar B, Dhole N, Shisode K, Chaudhar A (2008) Antioxidant and anti-inflammatory related activities of selected synthetic chalcones: structure-activity relationship studies using computational tools. Chem Pharm Bull 56:897-901 (Pubitemid 351949700)
13. Geronikaki AA, Gavalas AM (2006) Antioxidants and inflammatory disease: synthetic and natural antioxidants with anti-inflammatory activity. Comb Chem High Throughput Screen 9:425-442 (Pubitemid 44024700)
14. Gutteridge JM (1995) Lipid peroxidation and antioxidants as biomarkers of tissue damage. Clin Chem 41:1819-1828
15. Herencia F, Ferraindiz ML, Ubeda A, Dominguez JN, Charris JE, Lobo GM, Alcaraz MJ (1998) Synthesis and anti-inflammatory activity of chalcone derivatives. Bioorg Med Chem Lett 8:1169-1174 (Pubitemid 28231392)
16. Herencia F, Ferrándiz ML, Ubeda A, Guillén I, Dominguez JN, Charris JE, Lobo GM, Alcaraz MJ (2001) 4-dimethylamino-3,4-dimethoxy chalcones down regulates inos expression and exerts anti-inflammatory effects. Free Radic Biol Med 30:43-50 (Pubitemid 32008087)
17. Hsieh H-K, Lee T-H, Wang J-P, Wang J-J, Lin C-N (1998) Synthesis and anti-inflammatory effect of chalcones and related compounds. Pharm Res 15:39-46 (Pubitemid 28080864)
18. Hsieh H-K, Tsao L-T, Wang J-P (2000) Synthesis and anti-inflammatory effect of chalcones. J Pharm Pharmacol 52:163-171 (Pubitemid 30125298)
19. Kujubu DA, Fletcher BS, Varnum BC, Lim RW, Herschman HR (1991) TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue. J Biol Chem 266:12866-12872
20. Linn Y-M, Zhou Y, Flavin MT, Zhou L-M, Nie W, Chen F-C (2002) Chalcones and flavonoids as anti-tuberculosis agents. Bioorg Med Chem 10:2795-2802 (Pubitemid 34626243)
21. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the folin phenol reagent. Biol Chem 193: 265-275
22. Marnett LJ (2000) Cyclooxygenase mechanisms. Curr Opin Chem Biol 4:545-552
23. Miyachi H, Azuma A, Hioki E, Iwasaki S, Kobayashi Y, Hashimoto Y (1996) Inducer-specific bidirectional regulation by thalidomide and phenylphthalimides of tumor necrosis factor-alpha production. Biochem Biophys Res Commun 224:426-430 (Pubitemid 26268203)
24. Miyachi H, Azuma A, Ogasawara A, Uchimura E, Watanabe N, Kobayashi Y, Kato F, Kato M, Hashimoto Y (1997) Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance. J Med Chem 40:2858-2865
25. Nash T (1953) The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem J 55:416-421
26. Nicolaides DN, Fylaktakidou CF, Litinas KE, Hadjipavlou-Litina D (1998) Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives. Eur J Med Chem 33:715-724 (Pubitemid 29161321)
27. Pairet M, Engelhardt G (1996) Distinct isoforms (COX-1 and COX-2) of cyclooxygenase: possible physiological and therapeutic implications. Fundam Clin Pharmacol 10:1-15 (Pubitemid 26079294)
28. Sasaki K, Matsumato I, Beppu M (1991) Affinity Chromatography, Tokyo Kagaku Dojin: Tokyo
29. Satyanarayana M, Tiwari P, Tripathi BK, Srivastava AK, Pratab R (2004) Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. Bioorg Med Chem 12:883-889 (Pubitemid 38251280)
30. Shibata Y, Sasaki K, Hashimoto Y, Iwasaki S (1994) Tumor necrosis factor-a production enhancers with a phenylphthalimide skeleton. Biochem Biophys Res Commun 205:1992-1997
31. Tandon M, Tandon P, Barthwal JP, Bhalla TN, Bhargava KP (1982) Anti-inflammatory and anti-proteolytic activities of newer indolyl- isoquinilines. Drug Res 32:1233-1235 (Pubitemid 12034270)
32. Vane JR, Botting RM (1996) Mechanism of action of antiinflammatory drugs. Scand J Rheumatol 102:9-21
33. Wilson KP, McCaffrey PG, Hsiao K, Pazhanisamy S, Galullo V, Bemis GW, Fitzgibbon MJ, Caron PR, Murcko MA, Su MSS (1997) The structural basis for the specificity of pyridinylimidazole inhibitors of p38 MAP kinase. Chem Biol 4:423-431 (Pubitemid 27288707)
34. Xia Y, Yang ZY, Xia P, Bastow KI, Nakanishi Y, Lee K-H (2000) Antitumor agents. Part 202: novel 20-amino chalcones: design, synthesis and biological evaluation. Bioorg Med Chem Lett 10:699-701 (Pubitemid 30215866)