124752-25-6

Usage

Uses

Used in Pharmaceutical Industry:
6-aminocarbovir is used as an intermediate for the synthesis of Abacavir, an anti-HIV drug. Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase, resulting in inactive glucuronide and carboxylate metabolites. Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which selectively inhibits HIV reverse transcriptase by incorporating into viral DNA.

InChI:InChI=1/C11H14N6O/c12-9-8-10(16-11(13)15-9)17(5-14-8)7-2-1-6(3-7)4-18/h1-2,5-7,18H,3-4H2,(H4,12,13,15,16)/t6-,7+/m1/s1

Upstream product

• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 120443-30-3 carbovir 
• 162992-44-1 9-[cis-(1'R,4'S)-4'-acetoxymethyl-2'-cyclopenten-1'-yl]-9H-2-amino-6-chloropurine 
• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 
• 268737-87-7 ((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol 

Relevant academic research and scientific papers

6-deoxycarbovir: A xanthine oxidase activated prodrug of carbovir

(-)-(cis)-4-(2-Amino-9H-purin-9-yl)-2-cyclopentenyl carbinol (6-deoxycarbovir) was prepared in order to evaluate prodrug approaches to increased bioavailability of the anti-HIV agent, (-)-carbovir. Incubation experiments demonstrated that 6-deoxycarbovir was rapidly converted to (-)-carbovir by the enzyme, xanthine oxidase. Since xanthine oxidase activity is present in both the intestine and liver, a high first pass conversion to carbovir would be expected in vivo.

Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-l-homocysteine hydrolase

2-Modified aristeromycin derivatives and their related analogs were synthesized to investigate their inhibitory activity against human and Plasmodium falciparum S-adenosyl-l-homocysteine hydrolase (PfSAHH). 2-Fluoroaristeromycin showed a strong inhibitory activity against PfSAHH selectively and complete resistance to adenosine deaminase.

CYCLOPENTENYL PURINE DERIVATIVE OR SALT THEREOF

An object of the present invention is to provide a compound exhibiting an excellent drug efficacy as an anti-adenoviral agent, and an anti-adenoviral agent. The present invention provides an anti-adenoviral agent including a compound represented by General Formula [1] (in the formula, R1 represents a hydrogen atom, a halogen atom, an amino group which may be substituted, a monocyclic nitrogen-containing heterocyclic ring group which may be substituted (provided that a nitrogen atom forming the ring is bonded to a carbon atom to which R1 is bonded), a monocyclic nitrogen- and oxygen-containing heterocyclic ring group which may be substituted (provided that a nitrogen atom forming the ring is bonded to a carbon atom to which R1 is bonded), a C1-6 alkoxy group which may be substituted, a hydroxyl group which may be protected, or the like; R2 represents a hydrogen atom or an amino protecting group; R3 represents a C1-20 alkoxy group which may be substituted, an aryloxy group which may be substituted, an amino group which may be substituted, or the like; R4 represents a C1-20 alkoxy group which may be substituted, an aryloxy group which may be substituted, an amino group which may be substituted, or the like; and X represents an oxygen atom or a sulfur atom) or a salt thereof.

PREPARATION OF SYNTHETIC NUCLEOSIDES VIA π-ALLYL TRANSITION METAL COMPLEX FORMATION

This invention provides highly regioselective and stereoselective processes for preparing synthetic nucleosides. A process for the preparation of synthetic nucleosides is provided that comprises a) preparing a bicycloamide derivative, b) reacting the bicycloamide derivative with a nucleic acid base or heterocyclic base or salt thereof in the presence of a transition metal catalyst to form a cyclopentenecarboxamide, and c) cleaving a carboxamide group from the cyclopentenecarboxamide to form the synthetic nucleoside. The processes according to the invention can be used for the synthesis of a variety of anti-viral agents, including Abacavir, Carbovir, and Entecavir, as well as derivatives thereof.

Analogs of (1s,cis)-4-(2-amino-9h-purin -9-yl) -2-Cyclopentene-1-methanol as antiviral

The present invention relates to analogs of (1S, cis)-4-(2-amino-9H-purin-9-yl)-2-cyclopentene-1-methanol for use in treating viral infections.

Antiviral combination comprising nucleoside analogs

Antiviral and antitumor compositions are disclosed comprising a mixture of AZT, ribavirin, d4T or CS-87 with a compound of general formula: STR1 wherein Z is H, OH or NH2, Y is CH, and X is selected from the group consisting of H, N(R)2, SR, OR or halogen, wherein R is H, lower(C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically-acceptable derivatives thereof.

Dideoxycarbocyclic nucleosides

Antiviral and antitumor compounds are disclosed of general formula: STR1 wherein Z is H, OH or NH2, Y is CH or N, the bond indicated by C1 '--C2 ' is absent or, in combination with the C1 '--C2 ' bond is the unit CH=CH, and X is selected from the group consisting of H, N(R2), SR, OR or halogen, wherein R is H, lower (C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically acceptable salts thereof.

Optically-active isomers of dideoxycarbocyclic nucleosides

Antiviral and antitumor compounds are disclosed of general formula: STR1 wherein Z is H, OR' or NH2, wherein R' is H, (C1 -C4)-alkyl, aryl, CHO, (C1 -C16)alkanoyl or O=P(OH)2, Y is CH or N, and X is selected from the group consisting of H, N(R2), SR, OR' or halogen, wherein R is H, lower-(C1 -C4)alkyl, aryl or mixtures thereof, and the pharmaceutically-acceptable salts thereof.

Guanine derivatives having antiviral activity and their pharmaceutically acceptable salts

Amino acid esters of carbovir have been found to have improved bioavailability after oral administration compared with carbovir. The esters are particularly useful for the treatment of hepatitis B virus and retrovirus (e.g. human immunodeficiency virus) infections. A preferred amino acid ester is the valine ester.