141018-29-3

Usage

Uses

Used in Pharmaceutical Research:
2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE is used as a research compound for studying the binding and structural properties between adenosine receptor subtypes. Its high selectivity for adenosine receptors makes it a valuable tool in understanding the complex interactions and signaling pathways associated with these receptors, which can be crucial for the development of targeted therapeutics.
Used in Drug Development:
In the pharmaceutical industry, 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE is utilized as a lead compound for the development of new drugs targeting adenosine receptors. Its agonistic properties can be harnessed to create medications that modulate the activity of these receptors, potentially leading to treatments for a variety of conditions, including neurological disorders, cardiovascular diseases, and certain types of cancer.
Used in Diagnostic Applications:
2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE can also be employed as a diagnostic agent in the medical field. Its ability to selectively bind to adenosine receptors can be leveraged to develop imaging agents or diagnostic tools that help in the detection and monitoring of conditions related to adenosine receptor dysregulation.
Used in Neurological Research:
In the field of neuroscience, 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE is used as a research tool to investigate the role of adenosine receptors in neurological processes. This can provide insights into the underlying mechanisms of various neurological disorders and contribute to the development of targeted therapies for conditions such as epilepsy, Parkinson's disease, and Alzheimer's disease.

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

• 250386-15-3 Apadenoson 
• 155036-84-3 2-(5-phenyl)pentyn-1-yl-5'-N-ethylcarboxamidoadenosine 
• 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 academic research and scientific papers

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

Purine and deazapurine nucleosides: Synthetic approaches, molecular modelling and biological activity

A number of ligands for the adenosine binding sites has been obtained by using nucleoside convergent and divergent synthesis. Most of our nucleosides have been synthesized by coupling 2,6-dichloropurine (1), 2,6-dichloro-1-deazapurine (2), 2,6-dichloro-3-

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.

INDUCTION OF PHARMACOLOGICAL STRESS WITH ADENOSINE RECEPTOR AGONISTS

A method is provided employing A2A adenosine receptor agonists as vasodilators to detect the presence and assess the severity of coronary artery stenosis.

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

2-Alkynyl derivatives of adenosine and adenosine-5'-N-ethyluronamide as selective agonists at A2 adenosine receptors

In the search for more selective A2-receptor agonists and on the basis that appropriate substitution at C2 is known to impart selectivity for A2 receptors, 2-alkynyladenosines 2a-d were resynthesized and evaluated in radioligand binding, adenylate cyclase, and platelet aggregation studies. Binding of [3H]NECA to A2 receptors of rat striatal membranes was inhibited by compounds 2a-d with K(i) values ranging from 2.8 to 16.4 nM. 2- Alkynyladenosines also exhibited high-affinity binding at solubilized A2 receptors from human platelet membranes. Competition of 2-alkynyladenosines 2a-d for the antagonist radioligand [3H]DPCPX and for the agonist [3H]CCPA gave K(i) values in the nanomolar range, and the compounds showed moderate A2 selectivity. In order to improve this selectivity, the corresponding 2- alkynyl derivatives of adenosine-5'-N-ethyluronamide 8a-d were synthesized and tested. As expected, the 5'-N-ethyluronamide derivatives retained the A2 affinity whereas the A1 affinity was attenuated, resulting in an up to 10- fold increase in A2 selectivity. A similar pattern was observed in adenylate cyclase assays and in platelet aggregation studies. A 30- to 45-fold selectivity for platelet A2 receptors compared to A1 receptors was found for compounds 8a-c in adenylate cyclase studies.