21266-35-3

Upstream product

• 4261-14-7 9-benzyl-9H-purin-6-ylamine 
• 56046-34-5 9-benzyl-8-bromo-9H-purin-6-amine 
• 6974-78-3 8-bromoadenine 
• 21149-26-8 8-oxoadenine 
• 100-39-0 benzyl bromide 
• 66224-66-6 adenine 
• 100-46-9 benzylamine 
• 3173-56-6 benzyl isothiocyanate 

Relevant academic research and scientific papers

Synthetic strategies to 9-substituted 8-oxoadenines

Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Efficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives

An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, which are expected to have various biological activities, was realized. 5-amino-4-cyano-2-hydroxyimidazoles(1) were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of 1a with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines (2-6) possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (4 and 6) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines (5 and 7), respectively. 2-Alkythioadenines (15) were prepared by an analogous reaction of 1a with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles 1 are most useful intermediated for the synthesis of 8-hydroxyadenine derivatives.

Type 2 helper T cell-selective immune response suppressors

The present invention relates to a type 2 helper T cell-selective immune response inhibitor, an immune response regulator and an anti-allergic agent, individually comprising, as an active ingredient, a purine derivative represented by General Formula (I): wherein R2is hydrogen or a hydrocarbon group in which —CH2— not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C—H not directly bound to the purine skeleton may be substituted by N, C-halogen or C—CN; R6is hydroxyl, amino or amino which is mono- or di-substituted by a hydrocarbon group(s); R8is hydroxyl, mercapto, acyloxy or hydrocarbon group-substituting oxycarbonyloxy; and R9is a hydrocarbon group in which —CH2— not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C—H not directly bound to the purine skeleton may be substituted by N, C-halogen or C—CN; or its tautomer or a salt of the purine derivative or the tautomer.

Novel and efficient synthesis of 8-oxoadenine derivatives

A novel synthetic method of 8-oxoadenine derivatives (3 and 4) is reported. This widely applicable synthetic method was realized through the use of 5-amino-4-cyano-2-oxoimidazole derivatives (2) as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.

Purine derivative

PCT No. PCT/JP97/02310 Sec. 371 Date Mar. 3, 1998 Sec. 102(e) Date Mar. 3, 1998 PCT Filed Jul. 3, 1997 PCT Pub. No. WO98/01448 PCT Pub. Date Jan. 15, 1998This invention relates to novel purine derivatives of formula (I): where R2 and R9 are hydrocarbon groups, R6 is an amino group and R8 is a hydroxyl, or acyloxy group. These purine derivatives are effective at promoting secretion of interferon in patients, and can be used to treat diseases against which interferon is effective.