2′-C-Methyl Analogs of Selective Adenosine Receptor Agonists: Synthesis and Binding Studies was written by Franchetti, Palmarisa;Cappellacci, Loredana;Marchetti, Stefano;Trincavelli, Letizia;Martini, Claudia;Mazzoni, Maria R.;Lucacchini, Antonio;Grifantini, Mario. And the article was included in Journal of Medicinal Chemistry in 1998.Category: tetrahydrofurans This article mentions the following:
2′-C-Me analogs of selective adenosine receptor agonists such as (R)-PIA, CPA, CCPA, NECA, and IB-MECA were synthesized in order to further investigate the subdomain that binds the ribose moiety. Binding affinities of these new compounds at A1 and A2A receptors in bovine brain membranes and at A3 in rat testis membranes were determined and compared. It was found that the 2′-C-Me modification resulted in a decrease of the affinity, particularly at A2A and A3 receptors. When such modification was combined with N6-substitutions with groups which induce high potency and selectivity at A1 receptors, the high affinity was retained and the selectivity was increased. Thus, 2-chloro-2′-C-methyl-N6-cyclopentyladenosine (2′-Me-CCPA), which displayed a Ki value of 1.8 nM at A1 receptors, was selective for A1 vs A2A and A3 receptors by 2166- and 2777-fold, resp., resulting in one of the most potent and A1-selective agonists so far known. In functional assay, this compound inhibited forskolin-stimulated adenylyl cyclase activity with an IC50 value of 13.1 nM, acting as a full agonist. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol (cas: 205171-06-8Category: tetrahydrofurans).
(2R,3R,4R,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol (cas: 205171-06-8) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Category: tetrahydrofurans
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem