1431557-45-7

Basic information

• Product Name: 2’-deoxy-2’-fluoro-6-chloroguanosine-3’,5’-O-diacetate
• CAS NO: 1431557-45-7
• Molecular Weight: 387.755
• Mol File: 1431557-45-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2’-deoxy-2’-fluoro-6-chloroguanosine-3’,5’-O-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2’-deoxy-2’-fluoro-6-chloroguanosine-3’,5’-O-diacetate(1431557-45-7)
• EPA Substance Registry System: 2’-deoxy-2’-fluoro-6-chloroguanosine-3’,5’-O-diacetate(1431557-45-7)

Safety Data

• Hazardous Substances Data: 1431557-45-7(Hazardous Substances Data)

Usage

Properties

Chemical compound
Belongs to the class of nucleosides
Modified form of guanosine
Contains fluorine and chlorine atoms
Has two acetate groups
Useful in research and medicinal applications
Altered properties compared to natural nucleoside

Specific content

Name: 2’-deoxy-2’-fluoro-6-chloroguanosine-3’,5’-O-diacetate
Modifications: fluorine and chlorine atoms, acetate groups
Applications: research, medicinal, biochemistry, pharmacology, drug development
Interest to scientists and researchers in various fields

Upstream product

• 78842-13-4 2'-deoxy-2'-fluoroguanosine 
• 134444-75-0 2’-fluoro-2’-deoxyguanosine-3’,5’-O-diacetate 

Downstream Products

• 1431557-46-8 6-O-methyl-2’-fluoro-2’-deoxyguanosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 
• 1431557-47-9 6-O-methyl-2’-fluoro-2’-deoxyguanosine-5’-O-naphtyl(cyclohexoxy-L-alaninyl)phosphate 
• 1431557-49-1 6-O-methyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431557-50-4 6-O-methyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(cyclohexoxy-L-alaninyl)phosphate 
• 1431557-51-5 6-O-methyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 
• 1431558-38-1 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 
• 1431557-52-6 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431557-70-8 6-O-ethyl-2’-fluoro-2’-deoxyguanosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 
• 1431557-55-9 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-naphthyl(benzoxy-L-alaninyl)phosphate 
• 1431557-58-2 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-phenyl(benzoxy-L-alaninyl)phosphate 
• 1431557-59-3 2’-deoxy-2’-fluoro-6-chloroguanosine-5’-O-phenyl(ethoxy-L-alaninyl)phosphate 

Relevant articles and documents

Synthesis and Pharmacokinetic Evaluation of Siderophore Biosynthesis Inhibitors for Mycobacterium tuberculosis

MbtA catalyzes the first committed biosynthetic step of the mycobactins, which are important virulence factors associated with iron acquisition in Mycobacterium tuberculosis. MbtA is a validated therapeutic target for antitubercular drug development. 5′-O-[N-(Salicyl)sulfamoyl]adenosine (1) is a bisubstrate inhibitor of MbtA and exhibits exceptionally potent biochemical and antitubercular activity. However, 1 suffers from suboptimal drug disposition properties resulting in a short half-life (t1/2), low exposure (AUC), and low bioavailability (F). Four strategies were pursued to address these liabilities including the synthesis of prodrugs, increasing the pKa of the acyl-sulfonyl moiety, modulation of the lipophilicity, and strategic introduction of fluorine into 1. Complete pharmacokinetic (PK) analysis of all compounds was performed. The most successful modifications involved fluorination of the nucleoside that provided substantial improvements in t1/2 and AUC. Increasing the pKa of the acyl-sulfonyl linker yielded incremental enhancements, while modulation of the lipophilicity and prodrug approaches led to substantially poorer PK parameters.