CAS 50908-62-8

5′-N-Cyclopropylcarboxamidoadenosine

Description:

5′-N-Cyclopropylcarboxamidoadenosine, commonly referred to as CPA, is a synthetic nucleoside analog of adenosine. It features a cyclopropylcarboxamide group at the 5′ position of the adenosine molecule, which enhances its biological activity and selectivity for adenosine receptors. This compound is known for its role as a potent and selective agonist for the A3 adenosine receptor, which is implicated in various physiological processes, including modulation of inflammation and immune responses. CPA exhibits characteristics such as high solubility in aqueous solutions, making it suitable for biological studies. Its structural modifications contribute to its stability and receptor affinity, allowing for potential therapeutic applications in conditions like cancer, cardiovascular diseases, and neurodegenerative disorders. Additionally, the presence of the cyclopropyl group may influence its pharmacokinetic properties, including absorption and metabolism. Overall, 5′-N-Cyclopropylcarboxamidoadenosine represents a significant compound in pharmacological research, particularly in the context of adenosine receptor modulation.

Formula: C₁₃H₁₆N₆O₄

InChI: InChI=1S/C13H16N6O4/c14-10-6-11(16-3-15-10)19(4-17-6)13-8(21)7(20)9(23-13)12(22)18-5-1-2-5/h3-5,7-9,13,20-21H,1-2H2,(H,18,22)(H2,14,15,16)/t7-,8+,9-,13+/m0/s1

InChI key: InChIKey=MYNRELUCFAQMFC-QRIDJOKKSA-N

SMILES: O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@H](C(NC4CC4)=O)[C@H]1O

Synonyms:

• (2S,3S,4R)-5-(6-amino-9H-purin-9-yl)-N-cyclopropyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)
• 1-(6-Amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-beta-D-ribofuranuronamide
• 1-(6-Amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-β-<span class="text-smallcaps">D</span>-ribofuranuronamide
• 1-(6-Amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxyribofuranuronamide
• 5-(6-amino-9H-purin-9-yl)-N-cyclopropyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)
• 5′-N-Cyclopropylcarboxamide adenosine
• 5′-N-Cyclopropylcarboxamidoadenosine
• Adenosine 5′-N-cyclopropylcarboxamide
• Adenosine 5′-cyclopropylcarboxamide
• Adenosine-5'-(N-cyclopropyl)carboxamide
• N-Cyclopropyl adenosine-5'-carboxamide
• Ribofuranuronamide, 1-(6-amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-
• beta-D-Ribofuranuranamide, 1-(6-amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-
• β-<span class="text-smallcaps">D</span>-Ribofuranuronamide, 1-(6-amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-
• β-D-Ribofuranuronamide, 1-(6-amino-9H-purin-9-yl)-N-cyclopropyl-1-deoxy-

5''-(N-Cyclopropyl)carboxamidoadenosine

CAS: 50908-62-8

Ref: 7W-GN2398

5'-(N-Cyclopropyl)carboxamidoadenosine

CAS: 50908-62-8

5'-(N-Cyclopropyl)carboxamidoadenosine (5' CAPA) is a cyclic nucleotide analog. It has been shown to have photochemical properties and can be used as a fluorescent probe for the detection of DNA. 5' CAPA binds to the α subunit of RNA polymerase and inhibits transcription, which may result in reduced expression of proteins involved in growth control. Structural analysis has revealed that 5' CAPA binds to the catalytic site of the enzyme, sterically interfering with ATP binding. The inhibitory effect is reversible by removal of 5' CAPA from the reaction solution or by addition of cytosolic calcium chelators. 5' CAPA was found to have no effect on phycocyanin production by phytoplankton when added at concentrations up to 1 mM and did not affect transcription-polymerase chain reactions or regulatory processes in bacterial cells.
5'-(N-Cy

Formula: C₁₃H₁₆N₆O₄

Purity: Min. 95%

Molecular weight: 320.31 g/mol

Ref: 3D-NC07982

5'-(N-Cyclopropyl)carboxamidoadenosine

CAS: 50908-62-8

adenosine A2 receptor agonist

Formula: C₁₃H₁₆N₆O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 320.3

Ref: TM-T22523