28440-13-3

Usage

Uses

Used in Pharmaceutical Industry:
2',3'-O-isopropylideneinosine-5'-carboxylic acid is used as a key intermediate in the synthesis of nucleoside analogs for antiviral and anticancer drug development. The enhanced stability and bioavailability of 2',3'-O-isopropylideneinosine-5'-carboxylic acid, due to the isopropylidene group, make it a valuable candidate for the creation of effective therapeutic agents.
Used in Drug Conjugation:
2',3'-O-isopropylideneinosine-5'-carboxylic acid is used as a functional group for conjugation with other molecules in drug development. The presence of the carboxylic acid group at the 5' position enables the attachment of various moieties, which can improve the compound's targeting and delivery to specific cells or tissues, thereby increasing its therapeutic efficacy and reducing side effects.
Used in Medicinal Chemistry Research:
2',3'-O-isopropylideneinosine-5'-carboxylic acid serves as a valuable chemical entity in medicinal chemistry research, where it can be used to explore the structure-activity relationships of nucleoside analogs. 2',3'-O-isopropylideneinosine-5'-carboxylic acid can be modified and studied to understand its interactions with biological targets, such as viral or cancerous cells, and to optimize its pharmacological properties for improved therapeutic outcomes.

Upstream product

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

Downstream Products

• 1174010-40-2 C₄₆H₆₄N₂₂O₁₄S 
• 1174010-34-4 C₃₈H₅₆N₂₀O₁₃ 
• 1174010-28-6 C₄₈H₅₈N₂₀O₁₃ 
• 35788-21-7 adenosine 5'-carboxamide 
• 103201-28-1 (2S,3S,4R,5R)-5-[6-((S)-1-Benzyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-27-0 (2S,3S,4R,5R)-5-[6-((R)-1-Benzyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-26-9 (2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-25-8 (2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-((R)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-30-5 (2S,3S,4R,5R)-3,4-Dihydroxy-5-{6-[2-(3,4,5-trimethoxy-phenyl)-ethylamino]-purin-9-yl}-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-29-2 (2S,3S,4R,5R)-3,4-Dihydroxy-5-[6-(4-methoxy-phenylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid ethylamide 
• 103201-36-1 (2S,3S,4R,5R)-5-[6-(1-Ethyl-propylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid benzylamide 

Relevant academic research and scientific papers

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.

A new method for synthesis and angiogenic evaluation of leteprinim potassium and its novel analogs

We developed a novel pathway for the successful synthesis of leteprinim potassium 1, which is one of the candidate substances for treating Alzheimer's disease, and subsequently synthesized 4 types of corresponding novel derivatives 2-5 that have hypoxanthine or 2-chloro-6-aminopurine as the nucleobase. We then determined the angiogenic activity of these compounds by using human umbilical vein endothelial cells. Compounds 1-4 showed no angiogenic potencies judging from statistical analysis, student's t-test.

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.

New fluorescent adenosine A1-receptor agonists that allow quantification of ligand-receptor interactions in microdomains of single living cells

Fluorescence spectroscopy is becoming a valuable addition to the array of techniques available for scrutinizing ligand-receptor interactions in biological systems. In particular, scanning confocal microscopy and fluorescence correlation spectroscopy (FCS) allow the noninvasive imaging and quantification of these interactions in single living cells. To address the emerging need for fluorescently labeled ligands to support these technologies, we have developed a series of red-emitting agonists for the human adenosine A1-receptor that, collectively, are N6-aminoalkyl derivatives of adenosine or adenosine 5′-N-ethyl carboxamide. The agonists, which incorporate the commercially available fluorophore BODIPY [630/650], retain potent and efficacious agonist activity, as demonstrated by their ability to inhibit cAMP accumulation in chinese hamster ovary cells expressing the human adenosine A1-receptor. Visualization and confirmation of ligand-receptor interactions at the cell membrane were accomplished using confocal microscopy, and their suitability for use in FCS was demonstrated by quantification of agonist binding in small areas of cell membrane.

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.

RUTHENIUM TETRAOXIDE: A MILD REAGENT FOR THE OXIDATION OF 2',3'-O-ISOPROPYLIDENE PURINE NUCLEOSIDES

2',3'-O-Isopropylidene purine nucleosides have been oxidized with ruthenium tetraoxide to provide the corresponding 5'-carboxylic acids in quantitative yields under neutral conditions.

N6-substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors.

The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of m