Title compounds were obtained starting from the key imidazole intermediate, 5-amino-1-phenylmethyl-2-mercapto-1H-imidazole-4-carboxylic acid amide 5, readily derived from the base catalyzed rearrangement of a thiazole, 5-amino-2-phenylmethylaminothiazole-4-carboxylic acid amide 4. Alkylation of the thiol function on 5 with phenylmethyl and allylic chlorides gave compounds 6 and 7 respectively. Cyclization of 6 with a variety of esters afforded 8-phenylmethylthiohypoxanthines, 8-11. Similarly, 7 was cyclized to 8-allylthiohypoxanthines, 20-21. Compound 5 was also cyclized, but formed 8-mercaptohypoxanthines, 22-24. Alkylation of 8-mercaptohypoxanthines afforded 8-alkylthiohypoxanthines, 8, 9, 25 and 26 (see Scheme 2). Chlorination of 9-11 afforded 16-18; adenine 19 was derived from 16. Oxidation of hypoxanthines 8-11 with m-chloroperbenzoic acid gave the corresponding 8-phenylmethylsulfonyl derivatives 12–15. These derivatives proved resistant to nucleophilic displacement reactions with primary amines.
|Autori:||BIAGI G.; GIORGI I; LIVI O; F. PACCHINI; O. SALERNI; V. SCARTONI|
|Titolo:||New C(2)-substituted 8-alkylsulfanyl-9-phenylmethyl-hypoxanthines. III|
|Anno del prodotto:||2005|
|Appare nelle tipologie:||1.1 Articolo in rivista|