39491-53-7

Usage

Uses

Used in Pharmaceutical Industry:
5'-Ethylcarboxamido-2',3'-isopropylidene Adenosine is used as a template for the development of A2B adenosine receptor agonists for various therapeutic applications. Its full agonist properties, as demonstrated through its capacity to modulate cAMP levels in CHO cells expressing the hA2B receptor, make it a promising candidate for further research and development in the pharmaceutical field.
Used in Research and Development:
In the field of research and development, 5'-Ethylcarboxamido-2',3'-isopropylidene Adenosine is utilized as a valuable tool for studying the mechanisms and functions of A2B adenosine receptors. 5'-ETHYLCARBOXAMIDO-2',3'-ISOPROPYLIDENEADENOSINE can help scientists better understand the receptor's role in various biological processes and potentially lead to the discovery of new therapeutic strategies targeting these receptors.

InChI:InChI=1/C15H20N6O4/c1-4-17-13(22)9-8-10(25-15(2,3)24-8)14(23-9)21-6-20-7-11(16)18-5-19-12(7)21/h5-6,8-10,14H,4H2,1-3H3,(H,17,22)(H2,16,18,19)/t8-,9-,10?,14+/m0/s1

Upstream product

• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 75-04-7 ethylamine 
• 159647-45-7 (3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester 
• 39491-49-1 2',3'-O-isopropylideneadenosine-5'-carbonyl chloride 

Relevant academic research and scientific papers

NOVEL ADENOSINE A3 RECEPTOR AGONISTS

The invention realizes that a series of sulfonamido derivatives with a conserved uronamide group at the 5' position provide superior A3 receptor affinity as well as selectivity. These new adenosine agonists are sulfonamido deritatives N-substituted with aliphatic groups (cyclic or linear) or aromatic radicals.

Nucleosides and nucleotides. 200. Reinvestigation of 5′-N-ethylcarboxamidoadenosine derivatives: Structure-activity relationships for P3 purinoceptor-like proteins

The non-P1 and non-P2 muscle relaxant effect of ATP in rabbit thoracic aorta has recently been attributed to a putative P3 purinoceptor, which is activated by either adenosine or ATP. Since the physiological roles of this

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.

Modification of the 5' Position of Purine Nucleosides. 2. Synthesis and Some Cardiovascular Properties of Adenosine-5'-(N-substituted)carboxamides

We have shown previously that the esters of adenosine-5'-carboxylic acid (10) represent a new class of potent nontoxic coronary vasodilators.For example, the ethyl ester (12), which is active by an intraduodenal or intravenous route in dogs, causes a larg

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.