891497-81-7

Basic information

• Product Name: 1H-Purin-2-amine,6-(1H-imidazol-1-yl)-(9CI)
• Synonyms: 1H-Purin-2-amine,6-(1H-imidazol-1-yl)-(9CI)
• CAS NO: 891497-81-7
• Molecular Formula: C₈H₇N₇
• Molecular Weight: 201.18808
• Product Categories: VARIOUSAMINE
• Mol File: 891497-81-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Purin-2-amine,6-(1H-imidazol-1-yl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Purin-2-amine,6-(1H-imidazol-1-yl)-(9CI)(891497-81-7)
• EPA Substance Registry System: 1H-Purin-2-amine,6-(1H-imidazol-1-yl)-(9CI)(891497-81-7)

Safety Data

• Hazardous Substances Data: 891497-81-7(Hazardous Substances Data)

Usage

Purine derivative

Contains both a purine and an imidazole ring

Potent and selective inhibitor

Inhibits the enzyme adenosine deaminase

Key role in purine nucleoside metabolism

Adenosine deaminase plays a key role in the purine nucleoside metabolism

Increase in adenosine and deoxyadenosine levels

Inhibiting adenosine deaminase can lead to an increase in these molecules

Therapeutic applications

Potential applications in cancer, autoimmune diseases, and inflammatory disorders

Anti-inflammatory and immunosuppressive properties

May have additional beneficial effects in disease treatment

Promising candidate for further research

Has potential for further study and drug development.

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 

Relevant articles and documents

Structure and synthesis of 6-(substituted-imidazol-1-yl)purines: Versatile substrates for regiospecific alkylation and glycosylation at N9

X-ray crystal structures of several 6-(azolyl)purine base and nucleoside derivatives show essentially coplanar conformations of the purine and appended 6-(azolyl) rings. However, the planes of the purine and imidazole rings are twisted ～57° in a 2-chloro-6-(4,5-diphenylimidazol-1-yl)purine nucleoside, and a twist angle of ～61° was measured between the planes of the purine and pyrrole rings in the structure of a 6-(2,5-dimethylpyrrol-1-yl) purine nucleoside derivative. Shielding "above" N7 of the purine ring by a proximal C-H on the 6-azolyl moiety is apparent with the coplanar compounds, but this effect is diminished in those without coplanarity. Syntheses of 6-(azolyl)purines from both base and nucleoside starting materials are described. Treatment of 2,6-dichloropurine with imidazole gave 2-chloro-6-(imidazol-1-yl)purine. Modified Appel reactions at C6 of trityl-protected hypoxanthine and guanine derivatives followed by detritylation gave 6-(imidazol-1-yl)- and 2-amino-6-(imidazol-1-yl)purines. Imidazole was introduced at C6 of 2′,3′,5′-tri-O-acetylinosine by a modified Appel reaction, and solvolysis of the glycosyl linkage gave 6-(imidazol-1-yl)purine. Guanosine triacetate was transformed into the protected 2,6-dichloropurine nucleoside, which was subjected to SNAr displacement with imidazoles at C6 followed by glycosyl solvolysis to provide 2-chloro-6-(substituted-imidazol-1-yl)purines. Potential applications of these purine derivatives are outlined.