Synthesis of Mannich bases of 5-hydroxynapthalene-1,8-carbolactone as potential antifungal or antitumor agents.
Mannich bases of 5-hydroxynaphthalene-1,8-carbolactone 1 were prepared from various secondary amines or bulky primary amines and formaldehyde. They were isolated in almost all cases as hydrochlorides. These derivatives were submitted to in vitro antifungal and cytotoxic assays. The antifungal assays were performed against three strains of yeasts and five strains of human pathogenic fungi. Two of the tested compounds, 2i and 2j, exhibited interesting antifungal activities against Candida albicans and Candida tropicalis. The cytotoxic activity was evaluated towards L 1210 leukemia cells. Almost all of the Mannich bases had shown significant activity against this tumor cell line as values of IC50 less than or equal to 4 micrograms/ml are considered interesting. Only one derivative 2 developed better cytotoxicity than the parent compound 1.
Fillion
H
H
Institut des Sciences Pharmaceutiques et Biologiques, Université Claude Bernard, Lyon, France.
Porte
M
M
Bartoli
M H
MH
Bouaziz
Z
Z
Berlion
M
M
Villard
J
J
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D005658:Fungi / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D007939:Leukemia L1210 / Q000188:drug therapy; D008352:Mannich Bases / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009284:Naphthols / Q000138:chemical synthesis* / Q000494:pharmacology
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D007783:Lactones; D008352:Mannich Bases; D009284:Naphthols; C069421:5-hydroxynaphthalene-1,8-carbolactone