Synthesis and antiprotozoal evaluation of benzothiazolopyrroloquinoxalinones, analogues of kuanoniamine A

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 16, 2003, Pages 3407-3412

  Tapia, Ricardo A ^a   Prieto, Yolanda ^a   Pautet, Félix ^b   Walchshofer, Nadia ^b   Fillion, Houda ^b   Fenet, Bernard ^b   Sarciron, Marie Elizabeth ^b  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 AZIDOETHYL) 1H INDOLE 4,7 DIONE; 1 (2 AZIDOETHYL) 4,7 DIMETHOXY 1H INDOLE; 1 (2 BROMOMETHYL) 4,7 DIMETHOXY 1H INDOLE; 1 (2 TERT BUTYLCARBAMOYLETHYL) 1H INDOLE 4,7 DIONE; 1 (2 TERT BUTYLCARBAMOYLETHYL) 4,7 DIMETHOXY 1H INDOLE; 1,4 BENZOQUINONE; 2 (TERT BUTYLOXYCARBONYLOXIMINO) 2 PHENYLACETONITRILE; 4,7 DIMETHOXY 1H INDOLE 2 CARBOXYLIC ACID; 4,7 DIMETHYL 1H INDOLE; 6 (2 TERT BUTYLCARBAMOYLETHYL) 5,9 DIOXO 6,9 DIHYDRO 5H INDOLO[5,6 F][1,3]BENZOTHIAZOLE; 6 (2 TERT BUTYLCARBAMOYLETHYL) 5,9 DIOXO 6,9 DIHYDRO 5H INDOLO[6,5 F][1,3]BENZOTHIAZOLE; 6,7 DIHYDROBENZOTHIAZOLO[5,6 H]PYRROLO[1,2,3 DE]QUINOXALIN 11 ONE; 6,7 DIHYDROBENZOTHIAZOLO[6,5 H]PYRROLO[1,2,3 DE]QUINOXALIN 11 ONE; ACETONITRILE DERIVATIVE; AMINE; BENZOTHIAZOLE DERIVATIVE; IMINE; KUANONIAMINE A; QUINONE DERIVATIVE; QUINOXALINE DERIVATIVE; TERT BUTYLOXYCARBONYLAMINOETHYLINDOLOQUINONE; TRIFLUOROACETIC ACID; TRIMETHYLPHOSPHINE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIPROTOZOAL ACTIVITY; ARTICLE; BIOASSAY; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DEMETHYLATION; DIELS ALDER REACTION; DRUG SCREENING; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; REDUCTION; THIN LAYER CHROMATOGRAPHY; TOXOPLASMA GONDII;

LEISHMANIA SP.; TOXOPLASMA GONDII;

EID: 0038825823     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00311-0     Document Type: Article

References (15)

1. Molinski T.F. Chem. Rev. 93:1993;1825.
2. Faulkner J. Nat. Prod. Rep. 16:1999;155.
3. Carrol A.R., Scheuer P.J. J. Org. Chem. 55:1990;4426.
4. (a) The synthesis of 3 was performed through nitration of 2,5-dimethoxybenzaldehyde followed by a Henry reaction with nitromethane and a reductive cyclization as described by: Hollis Showalter H.D., Pohlmann G. Org. Proc. Int. 24:1992;484
5. (b) Bénéteau V., Besson T. Tetrahedron Lett. 42:2001;2673.
6. (c) See also: Rajeswari S., Drost K.J., Cava M.P. Heterocycles. 34:1992;1749.
7. (a) Tapia R.A., Prieto Y., Pautet F., Domard M., Sarciron M.-E., Walchshofer N., Fillion H. Eur. J. Org. Chem. 2002;4005
8. (b) Tapia, R. A.; Alegria, L.; Pessoa, C. D.; Salas, C.; Cortés, M. J.; Valderrama, J. A.; Sarciron, M.-E.; Pautet, F.; Walchshofer, N.; Fillion, H. Bioorg. Med. Chem. 2003, 11, 2175.
9. Hemetsberger H., Knittel D., Weidman H. Monatsh. Chem. 100:1969;1599.
10. Tani M., Ikegami H., Tashiro M., Hiura T., Tsukiota C., Kaneko C., Shimizu M., Uchida M., Aida Y., Yokoyama Y., Murakami Y. Heterocycles. 34:1992;2349.
11. An analogous synthesis of 3 in 28% overall yield was mentioned in: Roué, N. Doctorat de l'Université de Reims Champagne-Ardenne, 1996; p 71.
12. Ariza X., Urpi F., Viladomat C., Vilarrasa J. Tetrahedron Lett. 39:1998;9101.
13. Al Hariri M., Jouve K., Pautet F., Domard M., Fenet B., Fillion H. J. Org. Chem. 62:1997;405.
14. Marshall-Aubart K., Heathcock C.H. J. Org. Chem. 64:1999;16.
15. Sarciron M.-E., Walchshofer N., Paris J., Pétavy A.F., Peyron F. Parasite. 5:1998;359.