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Synthesis and Characterization of Steroid‐linked N‐(2‐Chloroethyl)nitrosoureas
Author(s) -
Eisenbrand Gerhard,
Fischer Jürgen,
Mühlbauer Karl,
Schied Georg,
Schreiber Joachim,
Tang Weici,
Zelezny Otto
Publication year - 1989
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19893221206
Subject(s) - chemistry , steroid , pyrrolidine , amino acid , stereochemistry , receptor , medicinal chemistry , biochemistry , hormone
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 17β‐amino‐3‐hydroxy‐1,3,5(10)‐estratriene or 17β‐O‐[4‐(6‐aminohexylamino)‐1, 4‐dioxo‐butyl]‐estradiol. Estradiol‐17β‐hemisuccinate is esterified with N‐(2‐hydroxyethyl)‐N′‐(2‐chloroethyl)‐N′‐nitrosourea (HECNU). Spectroscopic characteristics and relative binding affinities to steroid receptors are given.