113646-62-1

Basic information

• Product Name: 2-CHLORO-N6-CYCLOPENTYL-1-*DEAZAADENOSIN E
• Synonyms: 2-CHLORO-N6-CYCLOPENTYL-1-*DEAZAADENOSIN E;1-deaza-2-chloro-n(6)-cyclopentyladenosine;2-chloro-N(sup 6)-cyclopentyl-1-deazaadenosine;DCCA
• CAS NO: 113646-62-1
• Molecular Formula: C16H21ClN4O4
• Molecular Weight: 368.819
• Mol File: 113646-62-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 686.5°C at 760 mmHg
• Flash Point: 369°C
• Appearance: /
• Density: 1.76g/cm³
• Vapor Pressure: 8.68E-20mmHg at 25°C
• Refractive Index: 1.782
• CAS DataBase Reference: 2-CHLORO-N6-CYCLOPENTYL-1-*DEAZAADENOSIN E(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N6-CYCLOPENTYL-1-*DEAZAADENOSIN E(113646-62-1)
• EPA Substance Registry System: 2-CHLORO-N6-CYCLOPENTYL-1-*DEAZAADENOSIN E(113646-62-1)

Safety Data

• Hazardous Substances Data: 113646-62-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H21ClN4O4/c17-11-5-9(19-8-3-1-2-4-8)12-15(20-11)21(7-18-12)16-14(24)13(23)10(6-22)25-16/h5,7-8,10,13-14,16,22-24H,1-4,6H2,(H,19,20)/t10-,13-,14-,16-/m1/s1

Upstream product

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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.

MODULATORS OF 5'-NUCLEOTIDASE, ECTO AND THE USE THEREOF

Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by 5'-nucleotidase, ecto is also provided.

Potent and selective ligands for adenosine binding sites

A number of selective ligands for the different binding sites of adenosine have been synthesized and tested in several pharmacological models. The aim of these synthetic efforts is both to improve the knowledge of structure-activity relationships in the adenosine-related biological systems and to develop drugs from some of these molecules.