Hydrogenative desulphurization of thienopyrrolizinones: An easy and selective access to (Z)-phenethylidenepyrrolizinones with in vitro cytotoxic activity

European Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2010, Pages 1146-1150

  Perri, Vittoria ^a   Rochais, Christophe ^a   Sopkova de Oliveira Santos, Jana ^a   Legay, Rémi ^a   Cresteil, Thierry ^b   Dallemagne, Patrick ^a   Rault, Sylvain ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^b CNRS   (France)

Author keywords

Cytotoxicity; Desulphurization; Hydrogenation; Pyrrolizinone; Tripentone

Indexed keywords

1 BENZYL 3 (3 HYDROXY 4 METHOXYPHENYL) 5,6,7,7A TETRAHYDROPYRROLO[2,3 B]PYRROLIZIN 8 (1H)ONE; 3 (3 HYDROXY 4 METHOXY)PHENYL 8H THIENO[2,3 B]PYRROLIZIN 8 ONE; 3 [1 (3 HYDROXY 4 METHOXYPHENYL)ETHYLIDENE] 2,3 DIHYDRO 1H PYRROLIZIN 1 ONE; 3 [1 (4 CHLOROPHENYL)ETHYLIDENE] 2,3 DIHYDRO 1H PYRROLIZIN 1 ONE; 3 [1 (4 METHOXYPHENYL)ETHYLIDENE] 2,3 DIHYDRO 1H PYRROLIZIN 1 ONE; 3 BENZYLOXY 4 METHOXYPHENYL ACETONITRILE; 3 ISOPROPYL 2,3 DIHYDRO 1H PYRROLIZIN 1 ONE; 3 ISOPROPYLIDENE 2,3 DIHYDRO 1H PYRROLIZIN 1 ONE; COMBRETASTATIN A4; ISOINDOLE DERIVATIVE; MR 22388; PYRROLIZINE DERIVATIVE; TETRAHYDROPYRROLOISOINDOLONE DERIVATIVE; TETRAHYDROTHIENOPYRROLIZINONE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; COMPETITIVE INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DESULFURIZATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGENATION; IN VITRO STUDY; SQUAMOUS CELL CARCINOMA;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; INHIBITORY CONCENTRATION 50; KB CELLS; MOLECULAR STRUCTURE; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR; THIOPENTAL; THIOPHENES;

EID: 75849118917     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.12.021     Document Type: Article

References (15)

1. Rochais C., Dallemagne P., and Rault S. Anti-Cancer Agents Med. Chem. 9 4 (2009) 369-380
2. Lisowski V., Enguehard C., Lancelot J.C., Caignard D.H., Lambel S., Leonce S., Pierre A., Atassi G., Renard P., and Rault S. Bioorg. Med. Chem. Lett. 11 (2001) 2205-2208
3. Lisowski V., Léonce S., Kraus-Berthier L., Sopkova-de-Oliveira Santos J., Pierré A., Atassi G., Caignard D.H., Renard P., and Rault S. J. Med. Chem. 47 (2004) 1448-1464
4. Rochais C., Lisowski V., Dallemagne P., and Rault S. Tetrahedron Lett. 45 (2004) 6353-6355
5. Rochais C., Sopkova-de Oliveira Santos J., Dallemagne P., and Rault S. Heterocycles 68 (2006) 2063-2077
6. Rochais C., Lisowski V., Dallemagne P., and Rault S. Bioorg. Med. Chem. 14 (2006) 8162-8175
7. Rochais C., Vu Duc N., Lescot E., Bureau R., Meijer L., Dallemagne P., and Rault S. Eur. J. Med. Chem. 44 (2009) 708-716
8. Honma T., Hayashi K., Aoyama T., Hashimoto N., Machida T., Fukasawa K., Iwama T., Ikeura C., Ikuta M., Suzuki-Takahashi I., Iwasawa Y., Hayama T., Nishimura S., and Morishima H. J. Med. Chem. 44 (2001) 4615-4627
9. Kawanishi N., Sugimoto T., Shibata J., Nakamura K., Masutani K., Ikuta M., Hirai H., and Bioorg H. Med. Chem. Lett. 16 (2006) 5122-5126
10. Adams R., Miyano S., and Fles D. J. Am. Chem. Soc. 82 (1960) 1466-1468
11. Gold'farb Y.L., Taits S.Z., and Belen'kit L.I. Tetrahedron 19 (1963) 1851-1866
12. Li Q., and Sham H.L. Expert Opin. Ther. Pat. 12 11 (2002) 1663-1702
13. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 2 (1989) 209-211
14. Prinz H., Ishii Y., Hirano T., Stoiber T., Camacho-Gomez J.A., Schmidt P., Düssman H., Burger A.M., Prehn J.H., Günther E.G., and Umezawa K. J. Med. Chem. 46 15 (2003) 3382-3394
15. Zuse A., Schmidt P., Baasner S., Böhm K.J., Müller K., Gerlach M., Günther E.G., Unger E., and Prinz H. J. Med. Chem. 50 24 (2007) 6059-6066