141018-29-3

Basic information

• Product Name: 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE
• Synonyms: 5'-Ethylcarboxamido-2-iodo-D-adenosine;5'-Ethylcarboxamido-2-iodoadenosine;1-(6-AMino-2-iodo-9H-purin-9-yl)-1-deoxy-N-ethyl-β-D-ribofuranuronaMide;(2S,3S,4R,5R)-5-(6-amino-2-iodo-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide
• CAS NO: 141018-29-3
• Molecular Formula: C₁₂H₁₅IN₆O₄
• Molecular Weight: 464.214
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides
• Mol File: 141018-29-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 218-220°C
• Appearance: /
• Density: 2.38±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• PKA: 12.87±0.70(Predicted)
• CAS DataBase Reference: 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE(141018-29-3)
• EPA Substance Registry System: 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE(141018-29-3)

Safety Data

• Hazardous Substances Data: 141018-29-3(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

2-Iodo-5’-ethylcarboxamido Adenosine is a potent and selective adenosine receptor agonist (1,2). 2-Iodo-5’-ethylcarboxamido Adenosine can be used to determine binding and structural properties between receptor subtypes.

Upstream product

• 75-04-7 ethylamine 
• 141018-28-2 ethyl 1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-β-D-ribofuranuronate 
• 35109-88-7 2-iodoadenosine 
• 141018-25-9 (3aR,4R,6R,6aR)-(6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 141018-27-1 1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-β-D-ribofuranuroic acid 
• 141018-26-0 (3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 
• 162936-24-5 N-ethyl-1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-2',3'-O-isopropylidene-β-D-ribofuranuronamide 
• 1195939-18-4 C₁₅H₁₆IN₅O₇ 

Downstream Products

• 141018-30-6 HE-NECA 
• 250386-15-3 Apadenoson 
• 203794-21-2 (3aS,4S,6R,6aR)-6-[6-Amino-2-(3-hydroxy-3-phenyl-prop-1-ynyl)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide 

Relevant articles and documents

Synthesis of [1,2-3H]ethylamine hydrochloride and [ 3H]-labeled apadenoson for a human ADME study

Tritium-labeled [1,2-3H]ethylamine hydrochloride was prepared through a multiple-step sequence in high radioactive specificity. The labeled amine was isolated in high purity following cartridge filtration and used subsequently in the synthesis

Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5′-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5′-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5′-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of?potent A2A adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5′-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5′-substitution patterns.

METHODS FOR PREPARING 2-ALKYNYLADENOSINE DERIVATIVES

Disclosed are methods for preparing 2-alkynyladenosine derivatives of Formula (A): or a stereoisomer, pharmaceutically acceptable salt, hydrate, solvate, acid salt hydrate or isomorphic crystalline form thereof, the method comprising the step ofcontacting