111109-98-9

Basic information

• Product Name: (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
• Synonyms: (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
• CAS NO: 111109-98-9
• Molecular Weight: 375.815
• Mol File: 111109-98-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol(111109-98-9)
• EPA Substance Registry System: (2S,3R,4S,5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol(111109-98-9)

Safety Data

• Hazardous Substances Data: 111109-98-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 2004-06-0 6-Chloropurine riboside 
• 4294-16-0 N₆-Benzyladenosine 

Downstream Products

• 111109-99-0 (S)-2-amino-4-((((2S,3S,4R,5S)-5-(6-(benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid 
• 1341220-41-4 N₆-benzyl-S-adenosylmethionine iodide 

Relevant articles and documents

Structure-guided design of a methyl donor cofactor that controls a viral histone H3 lysine 27 methyltransferase activity

vSET (a viral SET domain protein) is an attractive polycomb repressive complex 2 (PRC2) surrogate to study the effect of histone H3 lysine 27 (H3K27) methylation on gene transcription, as both catalyze histone H3K27 trimethylation. To control the enzymatic activity of vSET in vivo with an engineered S-adenosyl-l-methionine (SAM) analogue as methyl donor cofactor, we have carried out structure-guided design, synthesis, and characterization of orthogonal vSET methyltransferase mutant/SAM analogue pairs using a "bump-and-hole" strategy.

N6,5'-disubstituted adenosine derivatives as partial agonists for the human adenosine A3 receptor

5'-(Alkylthio)-substituted analogues of N6-benzyl- and N6-(3- iodobenzyl)adenosine were synthesized in 37-61% overall yields. The affinities of these compounds for the adenosine A1, A(2A), and A3 receptors were determined using rat brain cortex, rat brain striata, and stably transfected human A3 receptors in HEK 293 cells, respectively. The compounds proved to be selective for the adenosine A3 receptor and displayed affinities in the nanomolar range. Compounds 8, 10, and 11 had the highest affinities for the A3 receptor with K(i) values ranging from 8.8 to 27.7 nM. In the N6-benzyl series, compound 4 (LUF 5403), with a 5'-methylthio group, maintained a reasonable affinity and had the highest selectivity for the A3 receptor. Compound 12 (LUF 5411), with an N6-(3-iodobenzyl) group and a 5'- (n-propylthio) substituent, had the highest A3 selectivity of all of the compounds and also displayed high affinity for this receptor (K(i) = 44.3 nM). The compounds were also evaluated for their ability to stimulate [35S]GTPγ[S] binding in cell membranes expressing the human adenosine A3 receptor. It appeared that the N6,5'-disubstituted adenosine derivatives behaved as partial agonists. Compounds 2, 4, 8, and 10 had the highest intrinsic activities. Additionally, when tested in a cAMP assay, these compounds also behaved as partial agonists.