120687-07-2

Basic information

• Product Name: (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine
• Synonyms: (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine
• CAS NO: 120687-07-2
• Molecular Weight: 279.299
• Mol File: 120687-07-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine(120687-07-2)
• EPA Substance Registry System: (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine(120687-07-2)

Safety Data

• Hazardous Substances Data: 120687-07-2(Hazardous Substances Data)

Usage

Description

(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is a chemical compound derived from adenosine, a nucleoside present in DNA and RNA. It consists of a purine base, a sugar moiety, and an acetyl group. (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is utilized in medicinal chemistry as a pharmacological tool for studying adenosine receptors. Its unique structure and potential therapeutic applications make it a promising candidate for the treatment of various diseases, including cancer, cardiovascular disorders, and neurological diseases.

Uses

Used in Pharmaceutical Research:
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is used as a pharmacological tool for studying adenosine receptors, which play a crucial role in various physiological processes. Understanding the interaction of this compound with adenosine receptors can provide valuable insights into the development of new drugs targeting these receptors.
Used in Drug Development:
Due to its potential therapeutic applications, (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is used as a starting point for drug development in the treatment of various diseases. Its unique structure allows for the design and synthesis of novel compounds with improved pharmacological properties.
Used in Cancer Treatment Research:
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is used as a research compound for exploring its potential in cancer treatment. Its interaction with adenosine receptors may provide new avenues for developing targeted therapies against cancer cells.
Used in Cardiovascular Disorder Research:
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is also used in the study of cardiovascular disorders, as adenosine receptors are known to be involved in the regulation of heart function and blood vessel tone. Understanding the effects of (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine on these receptors could lead to the development of new treatments for heart diseases.
Used in Neurological Disease Research:
(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine is used as a research tool in the investigation of neurological diseases, as adenosine receptors are implicated in the modulation of neuronal activity and neurotransmission. (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine may help in the development of new therapeutic strategies for neurological disorders.

Upstream product

• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 1445-45-0 Trimethyl orthoacetate 
• 104227-86-3 6-deoxypenciclovir 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 

Downstream Products

• 247081-81-8 2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyloxybut-1-yl)purine 

Relevant articles and documents

Production of recombinant human aldehyde oxidase in Escherichia coli and optimization of its application for the preparative synthesis of oxidized drug metabolites

Recombinant human aldehyde oxidase (AO) was expressed in Escherichia coli. Different cell disruption methods and conditions of cell culture in shake flasks and bioreactors and of biotransformation on an analytical scale were tested to optimize the synthesis of oxidized AO drug metabolites. The volumetric productivity was increased 24-fold by optimizing the cell culture conditions. The highest yield was achieved in a 25 L stirred tank bioreactor under non-oxygen-limited conditions and high lactose feed rate. Suspensions of highly concentrated and well-aerated whole cells at neutral pH and relatively low temperatures led to the best conversion. The solvent for the substrate and the buffering agent for the biotransformation had an important effect. In a biotransformation with AO, 210 mg of famciclovir was converted to diacetyl penciclovir a yield of 82 %. The optimized protocol represents a viable method for the preparative synthesis of oxidized AO metabolites of drugs. Drug metabolites: Recombinant human aldehyde oxidase is expressed in Escherichia coli. The highest volumetric productivity is achieved in a 25 L stirred tank bioreactor under non-oxygen-limited conditions and high lactose feed rate. In a biotransformation with concentrated whole cells at pH 7.4 and 30 °C, 210 mg of famciclovir is converted to diacetyl penciclovir in a yield of 82 %. The optimized protocol enables the preparative synthesis of oxidized aldehyde oxidase metabolites of drugs.

PROCESS FOR THE PREPARATION OF FAMCICLOVIR

The invention provides processes for making famciclovir with low levels of undesirable by-products. The present invention discloses a process comprises reacting a compound of formula I (acetic acid 2-acetoxymethyl-4-(5-amino-7-chloro-imidazo [4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a C1-C6 alkyl acetate and ammonium formate. The present invention further discloses a process comprises reacting a compound of formula I (acetic acid 2-- acetoxymethyl-4-(5-amino-7-chloro-imidazo[4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a mixture of a C1-C6 alkyl acetate, a C1-C4 alcohol and ammonium formate.

Purine derivatives and their pharmaceutical use

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