19083-21-7

Basic information

• Product Name: N,N-dimethyl-9-[2,3-O-(1-methylethylidene)-beta-D-glycero-pentofuranosyl]-9H-purin-6-amine
• CAS NO: 19083-21-7
• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.3583
• Mol File: 19083-21-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 539.2°C at 760 mmHg
• Flash Point: 279.9°C
• Density: 1.56g/cm³
• Vapor Pressure: 1.86E-12mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: N,N-dimethyl-9-[2,3-O-(1-methylethylidene)-beta-D-glycero-pentofuranosyl]-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-9-[2,3-O-(1-methylethylidene)-beta-D-glycero-pentofuranosyl]-9H-purin-6-amine(19083-21-7)
• EPA Substance Registry System: N,N-dimethyl-9-[2,3-O-(1-methylethylidene)-beta-D-glycero-pentofuranosyl]-9H-purin-6-amine(19083-21-7)

Safety Data

• Hazardous Substances Data: 19083-21-7(Hazardous Substances Data)

Upstream product

• 2620-62-4 N⁶,N⁶-Dimethyladenosine 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 
• 2620-62-4 N,N-dimethyladenosine 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 31199-61-8 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 58-63-9 Inosine 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 2004-06-0 6-Chloropurine riboside 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 
• 124-40-3 dimethyl amine 

Downstream Products

• 74397-38-9 5'-O-Benzyl-N⁶,N⁶-dimethyladenosine 
• 15502-55-3 5'-O-Benzoyl-N⁶,N⁶-dimethyl-2'3'-O-isopropylideneadenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 4566-77-2 ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 143995-02-2 N⁶-formyl-2',3'-O-isopropylideneadenosine 
• 143995-03-3 N⁶-formyl-2',3'-O-isopropylidene-N⁶-methyladenosine 
• 1381763-88-7 1-(4-(tert-butyl)phenyl)-3-(3-((((3aR,4R,6R,6aR)-6-(6-(dimethylamino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)propyl)urea 
• 1381763-89-8 1-(4-(tert-butyl)phenyl)-3-(3-((((2R,3S,4R,5R)-5-(6-(dimethylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)urea 
• 15087-42-0 5'-O-Benzoyl-N⁶,N⁶-dimethyladenosine 

Relevant articles and documents

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α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

ecto-5′-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor α,β-methylene-ADP (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N6-Monosubstitution was superior to symmetrical N6,N6-disubstitution. The most potent inhibitors were N6-(4-chlorobenzyl)- (10l, PSB-12441, Ki 7.23 nM), N6-phenylethyl- (10h, PSB-12425, Ki 8.04 nM), and N6-benzyl-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, Ki 9.03 nM). Replacement of the 6-NH group in 10g by O (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 nM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nucleotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.

Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: Structure-activity relationships of the nucleobase domain of 5′-O-[N-(salicyl)sulfamoyl]adenosine

5′-O-[N-(salicyl)sulfamoyl]adenosine (Sal-AMS) is a prototype for a new class of antitubercular agents that inhibit the aryl acid adenylating enzyme (AAAE) known as MbtA involved in biosynthesis of the mycobactins. Herein, we report the structure-based design, synthesis, biochemical, and biological evaluation of a comprehensive and systematic series of analogues, exploring the structure-activity relationship of the purine nucleobase domain of Sal-AMS. Significantly, 2-phenyl-Sal-AMS derivative 26 exhibited exceptionally potent antitubercular activity with an MIC99 under iron-deficient conditions of 0.049 μM while the N-6-cyclopropyl-Sal-AMS 16 led to improved potency and to a 64-enhancement in activity under iron-deficient conditions relative to iron-replete conditions, a phenotype concordant with the designed mechanism of action. The most potent MbtA inhibitors disclosed here display in vitro antitubercular activity superior to most current first line TB drugs, and these compounds are also expected to be useful against a wide range of pathogens that require aryl-capped siderphores for virulence.