35788-29-5

Basic information

• Product Name: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name)
• Synonyms: adenosine-5-(N-isopropyl)carboxamide
• CAS NO: 35788-29-5
• Molecular Formula: C₁₃H₁₈N₆O₄
• Molecular Weight: 322.3198
• Mol File: 35788-29-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 460.94°C (rough estimate)
• Density: 1.79g/cm³
• Refractive Index: 1.796
• CAS DataBase Reference: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name)(35788-29-5)
• EPA Substance Registry System: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name)(35788-29-5)

Safety Data

• Hazardous Substances Data: 35788-29-5(Hazardous Substances Data)

Usage

Description

(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name) is a complex organic molecule that features a tetrahydrofuran ring with a purine and carboxamide group attached. This molecule also includes a propan-2-yl side chain and multiple hydroxyl groups. It is a derivative of the nucleoside adenosine, which is known for its presence in important biological molecules such as ATP, DNA, and RNA. (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name)'s specific name highlights its stereochemistry and functional groups, which are crucial for understanding its potential interactions and activities within biological systems.

Uses

Used in Pharmaceutical Industry:
(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-N-(propan-2-yl)tetrahydrofuran-2-carboxamide (non-preferred name) is used as a potential therapeutic agent for various applications due to its adenosine derivative nature and the presence of a purine ring, which is a key component in many biologically active molecules. Its specific stereochemistry and functional groups may allow it to interact with biological targets in ways that could be harnessed for medicinal purposes.
Used in Research and Development:
In the field of scientific research, this compound serves as a valuable tool for studying the effects of stereochemistry and functional group variations on molecular interactions and biological activity. Researchers can use this compound to explore its potential as a lead molecule in the development of new drugs or to understand its interactions with specific biological systems.

Upstream product

• 222527-41-5 5'-N-isopropyl-2',3'-O-isopropylidenecarboxamidoadenosine 
• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 39491-49-1 2',3'-O-isopropylideneadenosine-5'-carbonyl chloride 

Relevant articles and documents

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.

Adenosine-5'-carboxylic acid amides

Adenosine-5'-carboxylic acid amides represented by the formula STR1 wherein R1 and R2 are each selected from the group consisting of hydrogen, loweralkyl, lowerhaloalkyl, lowerhydroxyalkyl, lowercycloalkyl, loweralkylcycloalkyl, loweralkenyl, lowerhaloalkenyl, lowerhydroxyalkenyl, loweralkynyl, lowerhaloalkynyl, benzylamino, phenyl, loweralkylphenyl, loweralkoxyloweralkyl, substituted phenyl, 2-methylfuran or di(C1 -C4)alkylamino(C1 -C4)alkyl, adamantyl or R1 and R2 taken together form a 5 or 6 membered heterocyclic moiety; R3 and R4 are hydrogen or acyl, or taken together form an isopropylidene or a benzylidene group; or a pharmaceutically acceptable acid addition salt thereof.