Structure-activity relationships in the acronycine and benzo[b]acronycine series: role of the pyran ring.
In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.
Do
Quyên
Q
Laboratoire de Pharmacognosie de l'Université Paris Descartes, U.M.R./C.N.R.S. n degrees 8638, Faculté de Pharmacie, 4 Avenue de l'Observatoire, 75006 Paris, France.
Thi Mai
Huong Doan
HD
Gaslonde
Thomas
T
Pfeiffer
Bruno
B
Léonce
Stéphane
S
Pierré
Alain
A
Michel
Sylvie
S
Tillequin
François
F
Dufat
Hanh
H
D000175:Acronine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; C436732:S 23906-1; D000175:Acronine