118353-05-2

Usage

Uses

Used in Pharmaceutical Industry:
Carbovir is used as an antiviral agent for the treatment of retroviral infections, such as HIV and hepatitis B. It works by interfering with the viral replication process, thereby helping to control the progression of the disease.
Used in Cancer Research:
Carbovir is used as a research tool in the study of cancer, particularly in the context of human hepatoma carcinoma cells. It has been found to cause mitochondrial toxicity in these cells, which can provide valuable insights into the development of novel cancer therapies.
Used in Drug Development:
Due to its antiviral properties, Carbovir is also used in the development of new drugs and therapies for the treatment of various viral infections. Its mechanism of action as an NRTI makes it a valuable compound for further research and potential application in the pharmaceutical industry.

InChI:InChI=1/C11H13N5O2/c12-11-14-9-8(10(18)15-11)13-5-16(9)7-2-1-6(3-7)4-17/h1-2,5-7,17H,3-4H2,(H3,12,14,15,18)

Upstream product

• 53837-32-4 cis-4-Hydroxy-2-cyclopenten-1-methanol 
• 229177-39-3 1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 124575-13-9 cis-4-p-toluenesulfonylaminocyclopent-2-enylmethanol 
• 109000-07-9 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 10310-21-1 2-Amino-6-chloropurin 
• 118237-87-9 cis-(+/-)-2-Amino-6-chloro-9-<4-(hydroxymethyl)-2-cyclopenten-1-yl>-9H-purine 
• 76909-89-2 cis-(+/-)-3-acetoxy-5-(acetoxymethyl)cyclopentene 
• 74877-20-6 methyl cis-(4-hydroxy-2-cyclopenten-1-yl)acetate 
• 140139-15-7 5-(dimethylthexylsilyloxymethyl)cyclopentanone 
• 144363-98-4 cis-5-dimethylthexylsilyloxymethyl-2-cyclopentenol 
• 141192-83-8 6-[2-(trimethylsilyl)ethoxy]-9H-purin-2-amine 
• 144363-96-2 5-dimethylthexylsilyloxymethyl-1-trimethylsilyloxycyclopentene 

Downstream Products

• 73-40-5 guanine 

Relevant academic research and scientific papers

Synthesis of cyclopentenyl carbanucleosides via palladium(0) catalysed reactions

Methyl 4-acetoxycyclopent-2-enylmethylcarboxylate (2) and the corresponding carbonate 3 have been treated with sodium salts and aluminum amides of pyrimidines, purines and methyl 1H-1,2,4-triazole-3-carboxylate with a catalyst formed from bis(dibenzylideneacetone)palladium(0) and triisopropyl phosphite to give the corresponding carbanucleosides in good to excellent yields. This method was also applied for a synthesis of carbovir (31).

π-Allylpalladium formation from allylic amines via N,N-ditosylimides and N-tosylamides: Efficient synthesis of the antiviral agent carbovir

Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford π-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (±)-carbovir (1) from cyclopentadiene in only seven steps and 13% overall yield.

New efficient method for the synthesis of the antiviral agent carbovir

An efficient synthesis of (±)-carbovir 1 and simple des(hydroxymethyl) analogues, e.g., 5, is reported which uses a new approach for attaching nucleoside bases to cycloalkene systems.

Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases

Allylic alkylation of amino- and hydroxy-azaheterocycles, in particular nucleoside bases, has been effected using Pd(0)-catalysis.A method has been developed for the preparation of carbocyclic nucleoside analogs such as the antiviral agent Carbovir.The synthesis of an appropriately substituted cyclopentenyl acetate for this reaction is described.Carbocyclic nucleosides of thymine at N-1, of adenine at N-9 and guanine at N-9 are described.Regiochemistry and stereochemistry of the products and intermediates have been determined by NMR studies.The (trimethylsilyl)ethyl group has been found to be an excellent protecting group for the 6-OH group in guanine, and it is readily removed by fluoride ions.

Pd(0)-catalyzed allylic alkylation in the synthesis of (±)carbovir

Racemic carbovir 1 has been synthesized in 6 steps from the cyclopentanone 8 with a Pd(0)-catalyzed allylation as a key reaction.

Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides

(±)-cis-[4-[(2,5-Diamino-6-chloropyrimidinyl)amino]-2-cyclopentenyl]c arbinol (5a) was synthesized from 2-amino-4,6-dichloropyrimidine and cis-4-(hydroxymethyl)cyclopenteylamine (2a) by subsequent preparation of the 5-[(4-chlorophenyl)azo] derivative of t