149007-83-0

Basic information

• Product Name: Adenosine, 2-chloro-N-cyclopropyl-
• Synonyms: Adenosine, 2-chloro-N-cyclopropyl-
• CAS NO: 149007-83-0
• Molecular Formula: C13H16ClN5O4
• Molecular Weight: 341.75024
• Mol File: 149007-83-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Adenosine, 2-chloro-N-cyclopropyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, 2-chloro-N-cyclopropyl-(149007-83-0)
• EPA Substance Registry System: Adenosine, 2-chloro-N-cyclopropyl-(149007-83-0)

Safety Data

• Hazardous Substances Data: 149007-83-0(Hazardous Substances Data)

Upstream product

• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 765-30-0 Cyclopropylamine 
• 13276-52-3 2,6-dichloropurine riboside 

Downstream Products

• 97374-48-6 N₆-cyclopentyladenosine 

Relevant articles and documents

Discovery of Potent and Selective Methylenephosphonic Acid CD73 Inhibitors

Solid tumors are often associated with high levels of extracellular ATP. Ectonucleotidases catalyze the sequential hydrolysis of ATP to adenosine, which potently suppresses T-cell and NK-cell functions via the adenosine receptors (A2a and A2b). The ectonucleotidase CD73 catalyzes the conversion of AMP to adenosine. Thus, increased CD73 enzymatic activity in the tumor microenvironment is a potential mechanism for tumor immune evasion and has been associated with poor prognosis in the clinic. CD73 inhibition is anticipated to restore immune function by skirting this major mechanism of adenosine generation. We have developed a series of potent and selective methylenephosphonic acid CD73 inhibitors via a structure-based design. Key binding interactions of the known inhibitor adenosine-5′-(α,β-methylene)diphosphate (AMPCP) with hCD73 provided the foundation for our early designs. The structure-activity relationship study guided by this structure-based design led to the discovery of 4a, which exhibits excellent potency against CD73, exquisite selectivity against related ectonucleotidases, and a favorable pharmacokinetic profile.

N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A1 adenosine receptor

A number of cycloalkyl substituents (from C-3 to C-8) have been introduced on the 6-amino group of adenosine, 1-deazaadenosine, and 2'- deoxyadenosine, bearing or not a chlorine atom at the 2-position, to evaluate the influence on the A1 and A(