15888-38-7

Usage

Chemical Properties

White Solid

Upstream product

• 109816-78-6 N⁶,O^5'-diacetyl-O^2'_,O3'-isopropyliden-adenosine 
• 108-05-4 vinyl acetate 
• 362-75-4 2',3'-isopropylidene adenosine 
• 103022-64-6 5'-acetyl-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 96695-35-1 5'-O-acetyl-2',3'-O-isopropylidene-N⁶,N⁶-di(phenoxycarbonyl)adenosine 
• 905581-18-2 ((3aR,4R,6R,6aR)-6-{6-[(anilinocarbonyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate 
• 362-75-4 2',3'-isopropylidene adenosine 
• 103022-64-6 5'-acetyl-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 905580-72-5 [(3aR,4R,6R,6aR)-6-(6-benzenesulfonylamino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate 
• 68074-34-0 O^5'-(4,4'-dimethoxy-trityl)-O^2'_,O3'-isopropylidene-adenosine 
• 105450-34-8 2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tri-p-bromobenzoyladenosine p-bromobenzoic acid salt 
• 103022-63-5 5'-O-(4,4'-dimethoxytrityl)-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 105471-08-7 7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tri-p-bromobenzoyl-8,5'-O-cycloadenosine 
• 105450-35-9 1-(5-O-bromobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-cyano-5-di-p-bromobenzoylaminoimidazole 
• 103022-65-7 4-cyano-5-p-cyanobenzoylamino-1-(5-O-p-cyanobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole 
• 105450-36-0 5-p-bromobenzoyl-1-(5-O-p-bromobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-cyanoimidazole 
• 103062-68-6 N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 76802-36-3 N⁶-p-toluoyl-2',3'-O-isopropylideneadenosine 

Relevant academic research and scientific papers

Deamination of 5′-substituted-2′,3′-isopropylidene adenosine derivatives catalyzed by adenosine deaminase (ADA, EC 3.5.4.4) and complementary enzymatic biotransformations catalyzed by adenylate deaminase (AMPDA, EC 3.5.4.6): A viable route for the preparation of 5′-substituted inosine derivatives

Adenosine deaminase (ADA) catalyzes the deamination of 2′,3′-isopropylidene adenosine and the corresponding 5′-amino derivative in a 3% dimethylsulfoxide aqueous solution. Whereas ADA is unable to convert other 5′-substituted derivatives (acetate, acetamido, azide), the enzyme adenylate deaminase (AMPDA) accepts all the above compounds as substrates for their biotransformation to the corresponding 5′-substituted inosine derivatives.

Identification of 8-aminoadenosine derivatives as a new class of human concentrative nucleoside transporter 2 inhibitors

Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 ± 3.8 μM), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 ± 0.19 μM). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.

Chemoselective N-Deacetylation of Protected Nucleosides and Nucleotides Promoted by Schwartz's Reagent

Protection and deprotection strategies involving the N-acetyl group are widely utilized in nucleoside and nucleotide chemistry. Herein, we present a mild and selective N-deacetylation methodology, applicable to purine and pyrimidine nucleosides, by means of Schwartz's reagent, compatible with most of the common protecting groups used in nucleoside chemistry.

INHIBITORS OF E1 ACTIVATING ENZYMES

This invention relates to compounds that inhibit El activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

Acyl migration from N6 to N7 of a 2',3'-O-isopropylideneadenosine derivative accompained by cyclonucleoside formation

Reaction of 2',3'-O-isopropylideneadenosine (1) with p-NCC6H4COCl in 1:6 Et3N-CH2Cl2 afforded the cyanoimidazole nucleoside 8 (53percent) and the 8,5'-O-cycloadenosine derivative 7 (29percent).Treatment of N6,N6-di-p-toluyl-2',3'-O-isopropilideneadenosine (23) with ZnBr2 in p-dioxane resulted in acyl migration from N6 to N7 to give the cycloadenosine derivative 4.The coordination site of the zinc cation on the base moiety of adenosine derivatives was determined by 15N nmr spectra.