60598-56-3Relevant academic research and scientific papers
New C(2)-substituted 8-alkylsulfanyl-9-phenylmethyl-hypoxanthines III
Biagi, Giuliana,Giorgi, Irene,Livi, Oreste,Pacchini, Federica,Salerni, Oreste LeRoy,Scartoni, Valerio
, p. 743 - 749 (2007/10/03)
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.
