5'-N-Ethylcarboxamidoadenosine

Base Information

• Chemical Name: 5'-N-Ethylcarboxamidoadenosine
• CAS No.: 35920-39-9
• Deprecated CAS: 100111-00-0,110282-65-0,74992-42-0,84272-21-9
• Molecular Formula: C12H16 N6 O4
• Molecular Weight: 317.35
• Hs Code.: 29349990
• European Community (EC) Number: 636-060-5,636-863-0
• DSSTox Substance ID: DTXSID801017234
• Nikkaji Number: J260.378K
• Wikidata: Q27087892
• Pharos Ligand ID: VWSXGHV42PN5
• Metabolomics Workbench ID: 52712
• ChEMBL ID: CHEMBL464859
• Mol file: 35920-39-9.mol

Synonyms:5' N Ethylcarboxamidoadenosine;5'-N-Ethylcarboxamidoadenosine;Adenosine 5' N ethyluronamide;Adenosine, N6-Ethyl-carboxamido;Adenosine-5'-(N-ethylcarboxamide);Adenosine-5'-N-ethyluronamide;N Ethylcarboxamidoadenosine;N-Ethylcarboxamidoadenosine;N6 Ethyl carboxamido Adenosine;N6-Ethyl-carboxamido Adenosine;NECA

Chemical Property of 5'-N-Ethylcarboxamidoadenosine

Chemical Property:

• Appearance/Colour: powder
• Melting Point: 229-231°C
• Boiling Point: °Cat760mmHg
• PKA: 12.93±0.70(Predicted)
• Flash Point: °C
• PSA: 148.41000
• Density: 1.87g/cm³
• LogP: -0.86410
• Storage Temp.: 2-8°C
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 308.12330301
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

99%, ^*data from raw suppliers

NECA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 22-26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Uses: A potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo Potent adenosine receptor agonist with some affinity at A1 and A2 receptors 5′-(N-Ethylcarboxamido)adenosine has been used:for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM)to determine nonspecific binding of adenosine receptorsto investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay

Technology Process of 5'-N-Ethylcarboxamidoadenosine

There total 8 articles about 5'-N-Ethylcarboxamidoadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

ethylamine (75-04-7,85404-22-4) + ethyl adenosine-5'-carboxylate (35803-57-7) → 5'-N-Ethylcarboxamidoadenosine (35920-39-9)

Guidance literature:

DOI:10.1021/jm00159a020

Reference yield:

5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-53-7) → 5'-N-Ethylcarboxamidoadenosine (35920-39-9)

Guidance literature:

With 80percent aq. TFA; at 20 ℃;

DOI:10.1021/jm000150k

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 5'-N-Ethylcarboxamidoadenosine (35920-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 3 h / 20 °C

2: dimethylformamide / 1 h / 20 °C

3: 80percent aq. TFA / 20 °C

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm000150k

upstream raw materials:

ethylamine

adenosine-5'-carboxylic acid 2-chloroethyl ester

ethyl adenosine-5'-carboxylate

5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine

Downstream raw materials:

(2S,3S,4R,5R)-5-(6-Amino-1-oxy-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide

N⁶-benzyl-5'-N-ethylcarboxamidoadenosine

2',3'-di-O-acetyladenosine-5'-(N-rthyl)carboxamide

Refernces

Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A₁ adenosine receptors

10.1016/j.bmc.2009.01.060

This research aims to synthesize and evaluate a series of 2-phenyl-9-benzyl-8-azapurines with an amido group at the 6 position as potential ligands for adenosine receptors, particularly focusing on the A1 subtype. The study involves synthesizing compounds with various substituents at the 6 position and testing their affinity for A1, A2A, and A3 adenosine receptors through radioligand binding assays. The results show that many of these compounds exhibit high affinity and selectivity for the A1 receptor compared to A2A and A3 receptors. Based on the biological data, QSAR models were developed using multiple linear regression and decision trees to predict the activity of new compounds. The models suggest that certain structural features, such as the presence of a cyclohexyl group, contribute to high affinity and selectivity for the A1 receptor. The study concludes that these findings can guide the design of new selective A1 adenosine receptor ligands, which have potential therapeutic applications. Key chemicals used in the research include 2-phenyl-9-benzyl-8-azapurines, various acyl chlorides for introducing different substituents, and radioligands like [3H]DPCPX, [3H]ZM241385, and [3H]NECA for binding assays.

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