Syntheses and cytotoxicities of four stereoisomers of muricatacin from D-glucose.
Four stereoisomers of muricatacin 1a-d were prepared by the reaction of corresponding aldehydes 4a-d, which in turn were prepared from D-glucose, with the anion of triethylphosphonoacetate followed by reduction and cyclization under acidic conditions. Cytotoxicities of four stereoisomers were tested against in vitro A-549 cell line as well as MCF-7 cell line. Stereochemistry at C4 and C5 position of muricatacin did not affect the cytotoxicities significantly.
Yoon
S H
SH
Department of Applied Chemistry, Ajou University, Suwon, Korea. shyoon@madang.ajou.ac.kr
Moon
H S
HS
Hwang
S K
SK
Choi
S
S
Kang
S K
SK
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005947:Glucose / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D005663:Furans; C082488:muricatacin; D005947:Glucose