Chemical modification of fumagillin. II. 6-Amino-6-deoxyfumagillol and its derivatives.
6-Amino-6-deoxyfumagillol (5) was synthesized by reductive amination of 6-oxo-6-deoxyfumagillol (4), which was obtained by oxidation of fumagillol (2). The reduction proceeded stereoselectively by the equatorial attack of hydride and 5 was found to have the same stereochemistry as that of 2. Several derivatives of 5 were prepared and most of them showed anti-angiogenic activity comparable to that of fumagillol derivatives.
Marui
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Chemistry Research Laboratories, Takeda Chemical Industries, Ltd., Osaka, Japan.
Kishimoto
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D000818:Animals; D003315:Cornea / Q000098:blood supply; D016222:Fibroblast Growth Factor 2 / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D009389:Neovascularization, Pathologic; D051381:Rats; D013055:Spectrophotometry, Infrared; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D013141:Spiro Compounds; D016222:Fibroblast Growth Factor 2; C075163:6-amino-6-deoxyfumagillol