Synthesis and antiproliferative activity of retroetoposide.
Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line.
Laboratoire de Pharmacochimie, UMR 176 CNRS-Institut Curie, Section Recherche, 26 rue d'Ulm, 75248 Paris cedex 05, France.
Philippe
P
Meresse
Prokopios
P
Magiatis
Emmanuel
E
Bertounesque
Claude
C
Monneret
D018906:Antineoplastic Agents, Alkylating / Q000138:chemical synthesis / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D005047:Etoposide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D018906:Antineoplastic Agents, Alkylating; D005047:Etoposide