Synthesis and characterization of steroid-linked N-(2-chloroethyl)nitrosoureas.
Syntheses of steroid-linked N-[N'-(2-chloroethyl)-N'-nitrosocarbamoyl]-(CNC-) amino acid esters and -amides with potential antineoplastic activity are described. The esters are prepared by reaction of CNC-amino acids with steroids using N,N'-carbonyldiimidazole and N,N'-dicyclohexylcarbodiimide. The corresponding amides are prepared by reaction of 1-(CNC-amino acyloxy)-pyrrolidine-2,5-diones with 17 beta-amino-3-hydroxy-1,3,5(10)-estratriene or 17 beta-O-[4-(6-aminohexylamino)-1,4-dioxo-butyl]-estradiol. Estradiol-17 beta-hemisuccinate is esterified with N-(2-hydroxyethyl)-N'-(2-chloro-ethyl)-N'-nitrosourea (HECNU). Spectroscopic characteristics and relative binding affinities to steroid receptors are given.
Eisenbrand
G
G
Fischer
J
J
Mühlbauer
K
K
Schied
G
G
Schreiber
J
J
Tang
W
W
Zelezny
O
O
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003432:Cross-Linking Reagents / Q000138:chemical synthesis*; D009607:Nitrosourea Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013256:Steroids / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D003432:Cross-Linking Reagents; D009607:Nitrosourea Compounds; D013256:Steroids; C013876:elmustine