7602-01-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetamido-6-chloropurine is used as a starting material for the synthesis of various pharmaceutical compounds due to its antiviral and antitumor properties. Its unique molecular structure allows for the development of new drugs and therapeutic agents that can target specific viral and tumor cells, offering potential treatments for a range of diseases.
Used in Antiviral Applications:
In the field of antiviral research, 2-Acetamido-6-chloropurine is utilized as an active compound to inhibit viral replication and reduce the severity of viral infections. Its antiviral properties make it a promising candidate for the development of new antiviral drugs.
Used in Antitumor Applications:
2-Acetamido-6-chloropurine is also used as an antitumor agent, where it can be employed to inhibit the growth and proliferation of tumor cells. Its potential in cancer treatment research is significant, as it may contribute to the development of novel cancer therapies.
Used in Drug Development Research:
In the realm of drug development, 2-Acetamido-6-chloropurine serves as a key component in the research and development of new pharmaceuticals. Its unique properties and biological activity make it a valuable asset in the creation of innovative treatments for various diseases and conditions.

InChI:InChI=1/C7H6ClN5O/c1-3(14)11-7-12-5(8)4-6(13-7)10-2-9-4/h2,4H,1H3,(H,9,10,11,13,14)

Upstream product

• 108-24-7 acetic anhydride 
• 10310-21-1 2-amino-6-chloropurine 
• 10310-21-1 2-Amino-6-chloropurin 

Downstream Products

• 109303-94-8 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamido-6-chloropurine 
• 140896-72-6 (E)-2-acetamido-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-4-(diisopropoxyphosphoryl)but-3-enyl>-6-chloropurine 
• 143056-35-3 N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine 
• 143056-36-4 N²-Acetyl-2-amino-6-chloro-7-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine 
• 214280-01-0 N-{9-[(3S,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-thiophen-3-yl]-6-chloro-9H-purin-2-yl}-acetamide 
• 857896-63-0 N-[6-chloro-9-[(3aS,4S,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-2-yl]acetamide 
• 911110-85-5 N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine 
• 911110-88-8 N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine 
• 1040918-19-1 C₃₁H₃₈N₆O₃Si 
• 1393669-08-3 2-acetylamino-6-chloro-9-(2',3'-dideoxy-3'-fluoro-5'-O-(4-phenylbenzoyl)-β-D-erythropentofuranosyl)-9H-purine 
• 1101849-71-1 C₃₈H₃₇ClN₈O₈ 

Relevant academic research and scientific papers

Synthesis of potentially prebiotic RNA precursors: Cytosine and guanine derivatives

The chemical synthesis of two potentially prebiotic monomers of RNA containing cytosine and guanine is reported.

COMPOSITIONS AND METHODS USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE

The present disclosure is directed, in part, to compounds, or pharmaceutically acceptable salts thereof, for the treatment and/or prevention of neurodegenerative disease and/or mitchonodrial disease including Parkinson's disease and Leigh's disease.

Synthesis of the hepatitis B nucleoside analogue lagociclovir valactate

2′,3′-Dideoxy-3′-fluoro-5-O-[(S)-(+)-2-(l-valyloxy) -propionyl guanosine (lagociclovir valactate) is a prodrug of 3′-fluoro-2′,3′-dideoxyguanosine with high oral bioavailability in humans and potent activity against hepatitis B virus (HBV). A five-step synthesis of lagocyclovir valactate starting from 2-amino-6-chloropurine is described. The synthesis was performed at kilogram scale, and the target nucleoside prodrug was isolated as the hemisulphate salt with an overall yield of 23%. The major challenges were N-glycosylation of a 2-deoxyfluorosugar, which required separation of α- and β-anomers, and deprotection of the penultimate intermediate by hydrogenation.

Studies on a potentially prebiotic synthesis of RNA

Current thinking supports an early phase of evolution in which information transfer and catalysis were mediated by evolving RNA. A novel potentially prebiotic synthesis of RNA is proposed involving polymerisation through aldol condensation followed by a retro-Amadori rearrangement and ring closure via a base-paired mesomeric heterocyclic betaine intermediate. The proposed monomer 1 is an achiral mixed phosphodiester and herein we report synthetic routes to 1 containing each of the four RNA bases, The solution phase behaviour of 1 containing adenine and uracil has been investigated and preliminary results of polymerisation experiments are also presented.

Process for preparing 2-acetylamino-6-chloropurine

[OBJECT] To provide an intended product of high quality at low production costs in a yield higher than in ordinary processes by using an inexpensive catalyst or a catalyst which can be readily recovered. [ARRANGEMENT] A process for preparing 2-acetylamino-6-chloropurine comprises suspending 2,9-diacetylguanine or 2-acetylguanine in a polar inert solvent, reacting with phosphorus oxychloride in the presence of a water-insoluble tertiary amine and either ammonium chloride or a hydrochloride of the tertiary amine, and hydrolyzing the resultant reaction product to obtain 2-acetylamino-6-chloropurine.

Process for the preparation of 2-acylamino-6-halopurine from 2,9-diacylguanine

2-Acylamino-6-halopurine can be prepared by halogenation of 2,9-diacylguanine (2-acylamino-6-oxo-9-acylpurine) with phosphorus oxychloride or phosphorus oxybromide in the presence of a base and of a salt with subsequent hydrolysis of the reaction product.

Synthesis of 2-aminopurine nucleosides via regiocontrolled glycosylation

The stereo- and regiocontrolled synthesis of pyranosyl 2-aminopurine nucleosides is described. Coupling of bissilylated N2-acetyl-2-aminopurine with peracetylated glucopyranosides (SnCl4, (CH2Cl)2-MeCN, reflux) afforded good yields of the corresponding N9-β-2-aminopurine nucleosides. Glycosylation of N2-acetyl-2-amino-6-chloropurine could be made to produce either N9-nucleosides (TMSOTf, (CH2Cl)2, reflux), or N7-nucleosides (SnCl4/MeCN, room temperature) selectively. Application of Knapp's thioglycoside procedure (NIS + TfOH, (CH2Cl)2, room temperature) produced the N9-nucleosides with either base. The 2-amino-6-chloropurine derivatives were converted to their corresponding 2-aminopurine nucleosides by hydrogenolysis (H2, Pd/C). A convenient NOESY protocol for establishing base regiochemistry and anomeric stereochemistry is also presented.