Amphimedosides A-C: synthesis, chemoselective glycosylation, and biological evaluation.
The amphimedosides, discovered in 2006, are the first examples of naturally occurring glycosylated alkoxyamines. We report syntheses of amphimedosides A-C that feature a stereoselective oxyamine neoglycosylation and found that these alkaloids display modest cytotoxicity toward seven diverse human cancer cell lines, exhibiting IC(50) values ranging from 3.0 μM to greater than 100 μM.
Department of Chemistry, Seattle University, Seattle, Washington 98122, USA. langenha@seattleu.edu
Joseph M
JM
Langenhan
Edouard
E
Mullarky
Derek K
DK
Rogalsky
James R
JR
Rohlfing
Anja E
AE
Tjaden
Halina M
HM
Werner
Leonardo M
LM
Rozal
Steven A
SA
Loskot
D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006031:Glycosylation; D006801:Humans; D020128:Inhibitory Concentration 50; D013237:Stereoisomerism
D000470:Alkaloids; D000606:Amino Sugars; D000970:Antineoplastic Agents; C581729:amphimedoside A; C581728:amphimedoside B; C581730:amphimedoside C