65174-96-1

Usage

InChI:InChI=1/C14H17N5O6/c1-6(21)23-10-8(3-20)25-14(11(10)24-7(2)22)19-5-18-9-12(15)16-4-17-13(9)19/h4-5,8,10-11,14,20H,3H2,1-2H3,(H2,15,16,17)/t8-,10-,11+,14-/m1/s1

Upstream product

• 15830-52-1 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 1040031-35-3 9-[5'-O-(tert-butyldiphenylsilyl)-β-D-arabinofuranosyl]adenine 
• 5536-17-4 arabinosyl adenine 

Downstream Products

• 65174-95-0 9-(2-O-acetyl-β-D-arabinofuranosyl)adenine 
• 65286-65-9 9-<3-O-acetyl-β-D-arabinofuranosyl>adenine 
• 74829-57-5 9-<2,5-di-O-acetyl-β-D-arabinofuranosyl>adenine 

Relevant academic research and scientific papers

Enzymatic regioselective and complete deacetylation of two arabinonucleosides

Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes.

Anticancer and antiviral effects and inactivation of S-adenosyl-L- homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues

Selectively protected adenine nucleosides were converted into 5'- carboxaldehyde analogues by Moffatt oxidation (dimethyl sulfoxide/dicyclohexylcarbodiimide/dichloroacetic acid) or with the Dess- Martin periodinane reagent. Hydrolysis of a 5'-fluoro-5'-S-methyl-5'-thio (α-fluoro thioether) arabinosyl derivative also gave the 5'-carboxaldehyde. Treatment of 5'-carboxaldehydes with hydroxylamine [or O-(methyl, ethyl, and benzyl)hydroxylamine] hydrochloride gave E/Z oximes. Treatment of purified oximes with aqueous trifluoroacetic acid and acetone effected trans-oximation to provide clean samples of 5'-carboxaldehydes. Adenosine (Ado)-5'- carboxaldehyde and its 4'-epimer are potent inhibitors of S-adenosyl-L- homocysteine (AdoHcy) hydrolase. They bind efficiently to the enzyme and undergo oxidation at C3' to give 3'-keto analogues with concomitant reduction of the NAD+ cofactor to give an inactive, tightly bound NADH-enzyme complex (type I cofactor-depletion inhibition). Potent type I inhibition was observed with 5'-carboxaldehydes that contain a ribo cis-2',3'-glycol. Their oxime derivatives are 'proinhibitors' that undergo enzyme-catalyzed hydrolysis to release the inhibitors at the active site. The 2'-deoxy and 2'-epimeric (arabinosyl) analogues were much weaker inhibitors, and the 3'-deoxy compounds bind very weakly. Ado-5'-carboxaldehyde oxime had potent cytotoxicity in tumor cell lines and was toxic to normal human cells. Analogues had weaker cytotoxic and antiviral potencies, and the 3'-deoxy compounds were essentially devoid of cytotoxic and antiviral activity.

Use of 9-(beta-D-arabinofuranosyl) adenine derivatives for the preparation of pharmaceutical compositions for the treatment of aids

9-(β-D-arabinofuranosyl)adenine, also commonly known as Ara-A or vidarabine, esters thereof, or a pharmaceutically acceptable salt thereof, possess antiviral activity against the HTLV-III/LAV virus implicated in acquired immune deficiency syndrome (AIDS). The invention is related to the use of compounds of formula I for the preparation of pharmaceutical compositions useful in the treatment of infections of the HTLV-III/LAV virus in patients.

9-(2-O-Acyl-β-D-arabinofuranosyl)-adenine compounds and method for their production

9-(2-O-Acyl-β-D-arabinofuranosyl)adenine compounds and their production by enzymatic removal of the 3-O-acyl and 5-O-acyl groups of a 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)adenine compound or a 9-(2,3,5-tri-O-acyl-β-D-arabinofuranosyl)adenine compound. The monoester compounds are useful as antiviral agents. The compounds are watersoluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

9-(3-O-Acyl-β-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)-adenine compounds, and method for their production

9-(3-O-Acyl-β-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)adenine compounds, and their production by reacting in each case the corresponding 5-silyl ether derivative with a tetraalkylammonium fluoride. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.