A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.
Five new unsaturated iridolactones 3-7 related to natural cytotoxic oxylipins, Tei 9826, and iridolactone 2, were prepared by parallel synthesis from natural aucubin. It was found that perpivaloyl iridoid glucosides 2, 3, and 4 were markedly cytotoxic against both L1210 and KB-3-1 cell lines.
Laboratoire de Pharmacognosie de l'Université Paris Descartes, U.M.R./C.N.R.S. n degrees 8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, F-75006 Paris, France.
Vokatsoa C
VC
Rakotondramasy
Christine
C
Mouriès
Xavier
X
Cachet
Abdelhak
A
Neghra
Missam
M
El Mourabet
François
F
Tillequin
Michel
M
Koch
Brigitte
B
Deguin
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003517:Cyclopentanes / Q000737:chemistry; D015195:Drug Design; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D057888:Iridoid Glucosides; D039823:Iridoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D003517:Cyclopentanes; D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; C006650:aucubin; C013905:cyclopentenone