28440-13-3

Basic information

• Product Name: 2',3'-O-Isopropylideneinosine-5'-carboxylic acid
• Synonyms: 2',3'-O-Isopropylideneinosine-5'-carboxylic acid
• CAS NO: 28440-13-3
• Molecular Formula: C₁₃H₁₄N₄O₆
• Molecular Weight: 352.29944
• Mol File: 28440-13-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 224-229 °C(Solv: acetone (67-64-1); ethyl ether (60-29-7))
• Boiling Point: 669.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.92
• PKA: 2.58±0.60(Predicted)
• CAS DataBase Reference: 2',3'-O-Isopropylideneinosine-5'-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-Isopropylideneinosine-5'-carboxylic acid(28440-13-3)
• EPA Substance Registry System: 2',3'-O-Isopropylideneinosine-5'-carboxylic acid(28440-13-3)

Safety Data

• Hazardous Substances Data: 28440-13-3(Hazardous Substances Data)

Usage

General Description

2',3'-O-isopropylideneinosine-5'-carboxylic acid is a chemical compound with potential application in the development of nucleoside analogs for antiviral and anticancer drugs. It is a derivative of inosine, a nucleoside that plays a critical role in various biochemical processes. The addition of an isopropylidene group at the 2' and 3' positions of the inosine molecule enhances its stability and bioavailability, making it a promising candidate for drug development. Moreover, the presence of a carboxylic acid group at the 5' position can potentially facilitate the conjugation of the compound with other molecules, increasing its efficacy and specificity. Overall, 2',3'-O-isopropylideneinosine-5'-carboxylic acid represents a valuable chemical entity with significant potential for pharmaceutical applications.

Upstream product

• 2140-11-6 2',3'-O-isopropylideneinosine 
• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 58-63-9 Inosine 

Downstream Products

• 104940-65-0 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride 
• 15475-13-5 1-deoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)-β-D-ribofuranuronic acid 
• 773072-11-0 N⁶-(4-benzyloxycarbonylaminobutyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine 
• 773072-12-1 N⁶-(4-benzyloxycarbonylaminobutyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine 
• 932740-13-1 N⁶-(3-benzyloxycarbonylaminopropyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine 
• 932740-14-2 N⁶-(5-benzyloxycarbonylaminopentyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine 
• 932740-15-3 N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine 
• 932740-10-8 N⁶-(3-benzyloxycarbonylaminopropyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine 
• 932740-11-9 N⁶-(5-benzyloxycarbonylaminopentyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine 
• 932740-12-0 N⁶-(8-benzyloxycarbonylaminooctyl)-5'-ethylamino-2',3'-isopropylidene-5'-oxo-5'-deoxyadenosine 
• 152918-47-3 2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide 
• 103201-24-7 N-ethyl-N⁶-cyclohexyladenosine-5'-uronamide 
• 103201-36-1 (2S,3S,4R,5R)-5-[6-(1-Ethyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid benzylamide 
• 103201-29-2 (2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-(4-methoxy-phenylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid ethylamide 

Relevant articles and documents

A Structure-Activity Relationship Study of Bitopic N 6-Substituted Adenosine Derivatives as Biased Adenosine A1 Receptor Agonists

The adenosine A1 receptor (A1AR) is a potential novel therapeutic target for myocardial ischemia-reperfusion injury. However, to date, clinical translation of prototypical A1AR agonists has been hindered due to dose limiting adverse effects. Recently, we demonstrated that the biased bitopic agonist 1, consisting of an adenosine pharmacophore linked to an allosteric moiety, could stimulate cardioprotective A1AR signaling in the absence of unwanted bradycardia. Therefore, this study aimed to investigate the structure-activity relationship of compound 1 biased agonism. A series of novel derivatives of 1 were synthesized and pharmacologically profiled. Modifications were made to the orthosteric adenosine pharmacophore, linker, and allosteric 2-amino-3-benzoylthiophene pharmacophore to probe the structure-activity relationships, particularly in terms of biased signaling, as well as A1AR activity and subtype selectivity. Collectively, our findings demonstrate that the allosteric moiety, particularly the 4-(trifluoromethyl)phenyl substituent of the thiophene scaffold, is important in conferring bitopic ligand bias at the A1AR.

Synthesis and biological evaluation of novel neamine-nucleoside conjugates potentially targeting to RNAs

Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs.

Deamination of 2′,3′-O-isopropylideneadenosine-5′- carboxylic acid catalyzed by adenosine deaminase (ADA) and adenylate deaminase (AMPDA): Influence of substrate ionization on the activity of the enzymes

Adenosine deaminase (ADA) and adenylate deaminase (AMPDA) catalyze the deamination of 2′,3′-O-isopropylideneadenosine-5′-carboxylic acid to the corresponding inosine derivative and dependence of the rate of enzymatic reaction on the ionization degree of the substrate has been studied at different pH values. Copyright Taylor & Francis Group, LLC.