35920-40-2

Basic information

• Product Name: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)
• CAS NO: 35920-40-2
• Molecular Formula: C₁₅H₂₀N₆O₄
• Molecular Weight: 348.3571
• Mol File: 35920-40-2.mol
• Article Data: 4

Chemical Properties

• Density: 1.88g/cm³
• Refractive Index: 1.864
• CAS DataBase Reference: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)(35920-40-2)
• EPA Substance Registry System: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)(35920-40-2)

Safety Data

• Hazardous Substances Data: 35920-40-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide" is a non-preferred name for a molecule with the molecular formula C15H20N6O4. (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name) consists of a purine ring (6-amino-9H-purin-9-yl) attached to a cyclopentyl group and a tetrahydrofuran-2-carboxamide moiety. The molecule is a derivative of adenosine and has two chiral centers resulting in four stereoisomers. (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclopentyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name) has potential biological and pharmacological significance due to its structural similarity to adenosine, which is involved in various physiological processes in the body. However, the specific properties and uses of this compound are not widely known due to its non-preferred name and limited research.

Upstream product

• 39491-49-1 2',3'-O-isopropylideneadenosine-5'-carbonyl chloride 
• 222527-44-8 (3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-N-cyclopentyl-2,2-dimethyl tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide 
• 1003-03-8 Cyclopentamine 
• 159647-45-7 (3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester 
• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 

Relevant articles and documents

Optimization of adenosine 5′-carboxamide derivatives as adenosine receptor agonists using structure-based ligand design and fragment screening

Structures of G protein-coupled receptors (GPCRs) have a proven utility in the discovery of new antagonists and inverse agonists modulating signaling of this important family of clinical targets. Applicability of active-state GPCR structures to virtual screening and rational optimization of agonists, however, remains to be assessed. In this study of adenosine 5′ derivatives, we evaluated the performance of an agonist-bound A2A adenosine receptor (AR) structure in retrieval of known agonists and then employed the structure to screen for new fragments optimally fitting the corresponding subpocket. Biochemical and functional assays demonstrate high affinity of new derivatives that include polar heterocycles. The binding models also explain modest selectivity gain for some substituents toward the closely related A 1AR subtype and the modified agonist efficacy of some of these ligands. The study suggests further applicability of in silico fragment screening to rational lead optimization in GPCRs.

5'-N-substituted carboxamidoadenosines as agonists for adenosine receptors

Novel as well as known 5'-N-substituted carboxamidoadenosines were prepared via new routes that provided shorter reaction times and good yields. Binding affinities were determined for rat A1 and A(2A) receptors and human A3 receptors. EC50 values were determined for cyclic AMP production in CHO cells expressing human A(2B) receptors. On all receptor subtypes relatively small substituents on the carboxamido moiety were optimal. Selectivity for the A3 receptor was found for several analogues (1a, 1d, 1h, and 1k). On A1 receptors a number of compounds, but not 5'-N-ethylcarboxamidoadenosine (NECA, 1b), showed small GTP shifts, which could be indicative of lower intrinsic activities at the A1 receptor. At the A(2B) receptor, derivatives 1i-k with modified ethyl substituents had reduced activities compared to the A(2B) reference agonist NECA (1b). Thiocarboxamido derivatives (8b and 8c) displayed considerable although decreased A(2B) receptor activity. The X-ray structure determination of compound 8b was carried out. Due to intramolecular hydrogen bonding between the carboxamido NH and the purine N3 in the crystal structure, the ribose moiety of this compound is in a syn conformation. However, theoretical calculations support that NECA (1b), and less so 8b, can readily adopt both the syn and the anti conformation, therefore not excluding the proposed anti mode of binding to the receptor.