Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17 beta-ol.
Steroidal nucleoside analogs were synthesized starting from testosterone. By reduction of the oxime of 17 beta-hydroxy-androst-4-en-3-one (testosterone), a mixture of the two amino epimers of C-3 were obtained. The 3 alpha-amino-androst-4-en-17 beta-ol was crystallized in 73% yield and coupled with 5-amino-4,6-dichloropyrimidine to give 3 alpha-(5'-amino-4'-chloro-pyrimidin-6'-yl)amino-androst-4-en-17 beta-ol. This compound was treated with triethyl orthoformate in acid media to give the corresponding purinyl steroid adduct 3 alpha-(6'-chloro-purin-9'-yl)-androst-4-en-17 beta-ol in 98% yield. This substance, in turn, was converted with good yield into the 6'-thio, 6'-methylamino, and 6'-diethyl aminopurinyl derivatives through nucleophilic reactions at C-6 of the purine nucleus.
Gelpi
María E
ME
Cátedra de Química Orgánica, Facultad de Agronomía, Universidad de Buenos Aires, Buenos Aires, Argentina. mgelpi@mail.agro.uba.ar
Cadenas
Raúl A
RA
Mosettig
Jorge
J
Zuazo
Beatriz N
BN
D000737:Androstenols / Q000138:chemical synthesis*; D003460:Crystallization; D003500:Cyclization; D006358:Hot Temperature; D019811:Hydroxylamine / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry; D011687:Purines / Q000138:chemical synthesis; D011743:Pyrimidines / Q000138:chemical synthesis; D013739:Testosterone / Q000031:analogs & derivatives / Q000737:chemistry
D000737:Androstenols; D009705:Nucleosides; D010091:Oximes; D011687:Purines; D011743:Pyrimidines; C455840:testosterone oxime; D019811:Hydroxylamine; D013739:Testosterone