86646-88-0

Basic information

• Product Name: 3,6,7,8-tetrahydro-3-((2-hydroxyethoxy)methyl)imidazo(4,5-d)(1,3)diazepin-8-ol
• Synonyms: 3,6,7,8-tetrahydro-3-((2-hydroxyethoxy)methyl)imidazo(4,5-d)(1,3)diazepin-8-ol
• CAS NO: 86646-88-0
• Molecular Formula: C9H14 N4 O3
• Molecular Weight: 0
• Mol File: 86646-88-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 521.2°C at 760 mmHg
• Flash Point: 269°C
• Appearance: /
• Density: 1.54g/cm³
• Vapor Pressure: 1.09E-11mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 3,6,7,8-tetrahydro-3-((2-hydroxyethoxy)methyl)imidazo(4,5-d)(1,3)diazepin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,7,8-tetrahydro-3-((2-hydroxyethoxy)methyl)imidazo(4,5-d)(1,3)diazepin-8-ol(86646-88-0)
• EPA Substance Registry System: 3,6,7,8-tetrahydro-3-((2-hydroxyethoxy)methyl)imidazo(4,5-d)(1,3)diazepin-8-ol(86646-88-0)

Safety Data

• Hazardous Substances Data: 86646-88-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14N4O3/c14-1-2-16-6-13-5-12-8-7(15)3-10-4-11-9(8)13/h4-5,7,14-15H,1-3,6H2,(H,10,11)

Upstream product

• 72079-78-8 3,6-Bis-trimethylsilanyl-6,7-dihydro-3H-imidazo[4,5-d][1,3]diazepin-8-one 
• 80585-31-5 6,7-dihydro-3-<<2-(p-toluoyloxy)ethoxy>methyl>imidazo<4,5-d><1,3>diazepin-8(3H)-one 
• 71222-44-1 6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one hydrochloride 
• 86646-99-3 6,7-dihydro-3-<(2-hydroxyethoxy)methyl>imidazo<4,5-d><1,3>diazepin-8(3H)-one 

Relevant articles and documents

Adenosine deaminase inhibitors. Synthesis and biological evaluation of (±)-3,6,7,8-tetrahydro-3-[(2-hydroxyethoxy)methyl]imidazo[4,5-d][1,3] diazepin-8-ol and some selected C-5 homologues of pentostatin

The synthesis of several analogues of (8R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo [4,5-d][1,3]diazepin-8-ol (pentostatin, 1a) is described. Ring closure of 2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone dihydrochloride (3) with triethyl orthoacetate or triethyl orthopropionate gave the C-5 methyl and ethyl ketoaglycons, 6,7-dihydro-5-methylimidazo[4,5-d][1,3]diazepin-8(3H)-one (4b) and 5-ethyl-6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one (4c), respectively. Stannic chloride catalyzed condensation of the pertrimethylsilyl derivatives of 4b and 4c with a protected glycosyl halide afforded anomeric mixtures of ketonucleosides 3-(2-deoxy-3,5-di-O-p-toluoyl-β- and -α-D-erythro-pentofuranosyl)-6,7-dihydro-5-methylimidazo[4,5-d][1,3]diaze pin-8(3H)-one (5b and 6b) and 3-(2-deoxy-3,5-di-O-p-toluoyl)-β- and -α-D-erythro-pentofuranosyl)-5-ethyl-6,7-dihydroimidazo[4,5-d][1,3]diazep in-8(3H)-one (5c and 6c), respectively. Subsequent separation of the anomers, followed by deprotection and reduction of 5b, 6b, and 5c, afforded the respective 8R and 8S isomers. Stannic chloride catalyzed condensation of pertrimethylsilyl ketoaglycon 4a with 2-(chloromethoxy)-1-(p-toluoyloxy)ethane to give ketonucleoside 6,7-dihydro-3-[[2-(p-toluoyloxy)ethoxy]methyl]imidazo[4,5-d][1,3]diazepin- 8(3H)-one (9a) was followed by deprotection to 6,7-dihydro-3[(2-hydroxyethoxy)methyl]imidazo[4,5-d][1,3]diazepin-8(3H)-on e (9b) and then reduction to the racemic acyclic pentostatin analogue (±)-3,6,7,8-tetrahydro-3-[(2-hydroxyethoxy)methyl]imidazo[4,5-d][1,3]diaz epin-8-ol (2). K(i) values for the in vitro adenosine deaminase (EC 3.5.4.4; type I; calf intestinal mucosa) inhibitory activities of 1b, 1c, and 2 were determined to be 1.6 x 10-8, 1.5 x 10-6, and 9.8 x 10-8 M, respectively. When compounds 2 and 9b were tested in combination with vidarabine against herpes simplex virus, type 1, in an HEp-2 plaque reduction assay, only compound 2 was able to potentiate the antiviral activity of vidarabine.