Synthesis and anti-inflammatory activity of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid and its ester derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 20, 2007, Pages 5709-5714

  Epifano, Francesco ^a   Genovese, Salvatore ^b   Sosa, Silvio ^c   Tubaro, Aurelia ^c   Curini, Massimo ^b  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

3 (4 Geranyloxy 3 methoxyphenyl) 2 trans propenoic acid; Anti inflammatory activity; Prenyloxyphenypropanoids; Rutaceae

Indexed keywords

1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YL 3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; 2 METHOXY 4 [3 METHOXY 3 OXOPROP 1 ENYL]PHENYL 3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; 2 METHOXYPHENYL 3 [4 [(3,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; 3 (4' GERANYLOXY 3' METHOXYPHENYL) 2 PROPENOIC ACID; 4 (ACETYLAMINO)PHENYL 3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; 4 [[3 [4 [(3,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOYL]OXY]PHENYL 3 [4 [(3,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 ETHYLPHENYL]PROP 2 ENOATE; 6 [[3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL] 1 METHYLENEPROP 2 ENYL]OXY] 9,10 DIMETHYLENE 9,10 DIHYDROANTHRACEN 2 YL 3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL]OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; ANTIINFLAMMATORY AGENT; GUAIACOL; HYDROQUINONE ESTER DERIVATIVE; INDOMETACIN; METHYL 2 [[3 [4 [(2,7 DIMETHYLOCTA 2,6 DIETHYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOYL]OXY]BENZOATE; METHYL 3 [3,4 BIS[[3 [4 [(3,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOYL]OXY]PHENYL]PROP 2 ENOATE; METHYL 4 [[3 [4 [(2,7 DIMETHYLOCTA 2,6 DIETHYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOYL]OXY] 3 METHOXYBENZOATE; PARACETAMOL; UMBELLIFERYL 3 [4 [(2,7 DIMETHYLOCTA 2,6 DIENYL)OXY] 3 METHOXYPHENYL]PROP 2 ENOATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CROTON OIL EAR TEST; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; INFLAMMATION; MALE; MOUSE; NONHUMAN; SCREENING TEST;

ANIMALS; ANTI-INFLAMMATORY AGENTS; DITERPENES; ESTERS; INFLAMMATION; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; PROPIONIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

ACRONYCHIA; MUS; RUTACEAE;

EID: 34548573518     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.058     Document Type: Article

References (15)

1. Prager R.H., and Thregold H.M. Aust. J. Chem. 19 (1966) 451
2. Curini M., Epifano F., Genovese S., Marcotullio M.C., and Menghini L. Anticancer Agents Med. Chem. 6 (2006) 571 and references cited herein
3. Chen Y.F., Tsai H.Y., and Wu T.S. Planta Med. 61 (1995) 2
4. Ali B.H., Bashir A.K., and Tanira M.O. Pharmacology 51 (1995) 356
5. Botting R.M. J. Physiol. Pharmacol. 57 (2006) 113
6. Ou S., and Kwok K.C. J. Sci. Food Agric. 84 (2004) 1261
7. Miles E.A., Zoubouli P., and Calder P.C. Nutrition 21 (2005) 389
8. Azuma Y., Ozasa N., Ueda Y., and Takagi N. J. Dent. Res. 65 (1986) 53
9. Shiratoki K., Ohgami K., Ilieva I., Jin X.H., Yoshida K., Kase S., and Ohno S. J. Ocul. Pharmacol. Ther. 21 (2005) 298
10. Macedo S.M., Lourenco F.L., Borelli P., Fock R.A., Ferreira Jr. J.M., and Farsky S.H. Toxicology 220 (2006) 126
11. Sheu S.Y., and Chiang H.C. Anticancer Res. 17 (1997) 3293
12. Yonathan M., Asres K., Assefa A., and Bucar F. J. Ethnopharmacol. 108 (2006) 462
13. Curini M., Epifano F., and Genovese S. Bioorg. Med. Chem. Lett. 15 (2005) 5049
14. 3 δ): 1.62 (s, 3H), 1.69 (s, 3H), 1.75 (s, 3H), 2.09-2.20 (m, 4H), 3.95 (s, 3H), 4.69-4.72 (m, 2H), 4.97-5.13 (m, 2H), 5.47-5.56 (m, 1H), 6.48 (d, 1H, J = 9.9 Hz), 6.74 (d, 1H, J = 12.4 Hz), 6.92 (d, 1H, J = 8.1 Hz) 7.15-7.29 (m, 4H), 7.54 (d, 1H, J = 8.1 Hz), 7.73 (d, 1H, J = 9.9 Hz), 7.86 (d, 1H, J = 12.4 Hz); ...
15. Tubaro A., Dri P., Del Bello G., Zilli C., and Della Loggia R. Agents Actions. 17 (1985) 347