Total synthesis and antiangiogenic activity of cyclopentane analogues of fumagillol.
Novel cyclopentane analogues of fumagillol were synthesized and their endothelial cell proliferation inhibitory activities were evaluated. The cyclopentane-fumagillol derivatives were synthesized from (-)-2,3-O-isopropylidene-D-erythronolactone via stereoselective glycolate Claisen rearrangement and intramolecular ester enolate alkylation as key steps.
New Drug Research Laboratories, Chong Kun Dang Research Institute, Cheonan 330-831, Republic of Korea.
Byeong-Seon
BS
Jeong
Nam Song
NS
Choi
Soon Kil
SK
Ahn
Hoon
H
Bae
Hak Sung
HS
Kim
Deukjoon
D
Kim
D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D003510:Cyclohexanes; D003517:Cyclopentanes / Q000737:chemistry*; D004730:Endothelium, Vascular / Q000166:cytology; D006016:Glycolates / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D007941:Leukemia P388 / Q000188:drug therapy / Q000473:pathology; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000475:Alkenes; D020533:Angiogenesis Inhibitors; D003510:Cyclohexanes; D003517:Cyclopentanes; D006016:Glycolates; D007783:Lactones; D012717:Sesquiterpenes; C031149:glycolic acid; C057299:fumagillol; C013658:propylene