7674-36-4

Upstream product

• 56046-25-4 6-amino-9-benzyl-2-chloropurine 
• 6336-42-1 2-amino-9-benzyl-6-chloro-9H-purine 
• 100-39-0 benzyl bromide 
• 10310-21-1 2-Amino-6-chloropurin 
• 1904-98-9 2,6-diaminopurine 
• 5451-40-1 2,6 dichloropurine 
• 1839-18-5 2-chloroadenine 
• 68462-61-3 ethyl 5‐amino‐1‐benzyl‐1H‐imidazole‐4‐carboxylate 
• 228263-00-1 9-benzyl-2,6-bis(ethoxycarbonyl)purine 
• 228262-99-5 5-amino-1-benzyl-4-imidazolecarboxylic acid 
• 50-01-1 guanidine hydrochloride 
• 60598-48-3 5-amino-1-benzyl-1H-imidazole-4-carbonitrile 

Downstream Products

• 226907-93-3 6-Amino-9-benzyl-2-butylaminopurine 
• 226908-43-6 2-amino-9-benzyl-8-hydroxyadenine 
• 226908-04-9 2,6-diamino-9-benzyl-8-bromopurine 
• 328378-73-0 6-Amino-9-benzyl-3-{2-[(diisopropyloxyphosphoryl)methoxy]ethyl}-9H-purin-2(3H)-one 
• 328378-72-9 9-Benzyl-2{2-[(diisopropyloxyphosphoryl)methoxy]ethoxy}-9H-purin-6-amine 
• 226908-63-0 6-Amino-9-benzyl-2-(2-hydroxyethoxy)-9H-purin-6-amine 
• 7674-33-1 6-Amino-9-benzyl-9H-purin-2(3H)-one 

Relevant academic research and scientific papers

8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide

2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified.

Nucleic acid related compounds. 136. Synthesis of 2-amino- and 2,6-diaminopurine derivatives via inverse-electron-demand Diels-Alder reactions

Thermal inverse-electron-demand Diels-Alder reactions of 5-aminoimidazoles and 2,4,6-tris-(ethoxycarbonyl)-1,3,5-triazine (2) with spontaneous retro-Diels-Alder loss of ethyl cyanoformate and elimination of ammonia give 2,6-bis(ethoxycarbonyl)purines. A report that selective alkaline hydrolysis followed by acid-catalyzed decarboxylation gave 6-(ethoxycarbonyl)purine products was not in harmony with known reactions in purine chemistry. Our reinvestigation has shown that the 6-(ethoxycarbonyl) group undergoes preferential base-promoted hydrolysis, as expected, but regioselectivity for attack of hydroxide at the carbonyl group at C6 is not high (relative to hydrolysis of both C2 and C6 esters). The structure of 9-benzyl-2- (ethoxycarbonyl)purine was determined by X-ray crystallography and confirmed by Curtius rearrangement of the azidocarbonyl analogue to give 2-amino-6- benzylpurine. Acid-catalyzed decarboxylation of the 2,6-dicarboxylate formed during hydrolysis gave 9-benzylpurine, and Curtius rearrangement of 2,6-bis(azidocarbonyl)-9-benzylpurine gave 2,6-diamino-9-benzylpurine. Attempted applications of inverse-electron-demand Diels-Alder reactions of 2 with nucleoside derivatives were problematic.

Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: Discovery of 8-mercaptoadenines as potent interferon-inducers

Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine (9) indicated the most potent activity with MEC of 0.001 μM.

Synthesis and structure-activity relationships of 2-amino-8- hydroxyadenines as orally active interferon inducing agents

Recently, we have reported the 8-hydroxyadenine derivatives (2-4) as a novel class of interferon (IFN) inducing agents. In the present study, a series of 8-hydroxyadenines, which possess various amino moieties at the adenine C(2)-position, were synthesized and evaluated for their ability to induce endogenous IFN in comparison to the known active agent, Imiquimod. Among the compounds prepared, compound 9o possessing a 2-methoxyethylamino group at C(2)-position of adenine was found to exhibit potent IFN inducing activity in vivo. Compound 9o induced IFN from the dosage of 0.1 mg/kg, which was 30-fold potent than that of Imiquimod, and showed a good oral bioavailability (F=81%).

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.