226908-30-1

Upstream product

• 1839-18-5 2-chloroadenine 
• 352-11-4 1-chloromethyl-4-fluorobenzene 

Downstream Products

• 1026968-28-4 9-(4-fluoro-benzyl)-N²-pyridin-4-ylmethyl-9H-purine-2,6-diamine 
• 1027222-86-1 N²-benzyl-8-bromo-9-(4-fluoro-benzyl)-9H-purine-2,6-diamine 
• 1026265-08-6 N²-benzyl-9-(4-fluoro-benzyl)-9H-purine-2,6-diamine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel 9-substituted-8-hydroxyadenine derivatives as potent interferon inducers

Recently we reported the adenine derivatives 3a-d as novel interferon (IFN) inducers. In the present study, we conducted a detailed structure-activity relationship study of analogues of 3a-d with respect to their IFN-inducing activity, mainly focusing on the N(9)-position of the adenine. From this study, we found that introduction of the 3-pyridylmethyl moiety was effective to increase in vitro activity, and compound 9ae was identified as being the most potent IFN inducer. This compound gave a minimum effective concentration (MEC) of 3 nM, which is comparable with that of R-848, a second generation IFN inducer. Compound 9ae also demonstrated potent IFN-inducing activity at a dose of 0.1 mg/kg by oral administration in mice. Furthermore, compound 9ae induced IFN in monkeys in a dose dependent manner, with a potency superior to that of R-848. In addition, 9ae did not cause emesis in ferrets even at a dose of 30 mg/kg. In this study the maximum plasma concentration of 9ae was 1019 ng/mL (ca. 3.1 μM), which was approximately 1000-fold higher than the MEC value. Therefore, with respect to both the efficacy and the safety margin, compound 9ae (SM-276001) is considered to be a promising compound as an orally active IFN inducer.

Heterocyclic compounds

The present invention relates to a heterocyclic compound of the following general formula (I): wherein X is sulfur atom, oxygen atom or —NR3— (R3may form a heterocyclic ring or a substituted heterocyclic ring with R1via the nitrogen atom), R1is alkyl group, substituted alkyl group, aryl group, substituted aryl group, heterocyclic group or substituted heterocyclic group, and R2is hydrogen atom, halogen atom etc.; or its pharmaceutically acceptable salt and interferon inducers, antiviral agents, anticancer agents and therapeutic agents for immunologic diseases comprising the compound (I) or its pharmaceutically acceptable salt as active ingredients.