Synthesis and biological evaluation of analogs of the marine toxin polycavernoside A.
Second generation analogs of polycavemoside A (2) possessing a side chain at C-15 different from that of the natural toxin have been synthesized. The in vivo toxicities of these new compounds (expressed as the minimal lethal dose) have been evaluated in mice (ip) and compared to 2, its aglycone (8), and polycavemoside B (9). The bioactivity profile of enynene 5 is particularly notable.
Barriault
L
L
Evans Chemical Laboratories, The Ohio State University, Columbus 43210, USA.
Boulet
S L
SL
Fujiwara
K
K
Murai
A
A
Paquette
L A
LA
Yotsu-Yamashita
M
M
D000818:Animals; D004187:Disaccharides / Q000138:chemical synthesis* / Q000633:toxicity*; D018942:Macrolides / Q000138:chemical synthesis* / Q000633:toxicity*; D008297:Male; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000633:toxicity*; D051379:Mice; D008815:Mice, Inbred Strains; D013329:Structure-Activity Relationship; D018675:Toxicity Tests
D004187:Disaccharides; D018942:Macrolides; D008387:Marine Toxins; C121303:polycavernoside A; C121304:polycavernoside B