82855-66-1

Basic information

• Product Name: 1-pentofuranosyl-4-(phenylamino)pyrimidin-2(1H)-one
• CAS NO: 82855-66-1
• Molecular Formula: C₁₅H₁₇N₃O₅
• Molecular Weight: 319.3126
• Mol File: 82855-66-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 571°C at 760 mmHg
• Flash Point: 299.1°C
• Density: 1.56g/cm³
• Vapor Pressure: 7.06E-14mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 1-pentofuranosyl-4-(phenylamino)pyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-pentofuranosyl-4-(phenylamino)pyrimidin-2(1H)-one(82855-66-1)
• EPA Substance Registry System: 1-pentofuranosyl-4-(phenylamino)pyrimidin-2(1H)-one(82855-66-1)

Safety Data

• Hazardous Substances Data: 82855-66-1(Hazardous Substances Data)

Usage

Chemical class

Pyrimidine analog

Structural components

Pentofuranose sugar group, pyrimidine ring, phenylamino substituent at position 4

Potential medicinal properties

Antiviral and anticancer therapy

Mechanism of action

Inhibition of specific enzymes and pathways involved in viral and cancer cell replication

Status of research

Ongoing studies into biological activity and therapeutic applications

Potential use

Drug development target

Upstream product

• 14057-18-2 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 
• 58-96-8 uridine 
• 82855-63-8 4-(3-nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-one 
• 82855-62-7 4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one 
• 3083-77-0 araU 
• 3736-77-4 2,2'-Anhydrouridine 
• 62-53-3 aniline 

Relevant articles and documents

4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cytosine (Ara-C)

Treatment of the acetylated derivative (3b), which was prepared from uridine in 86 percent overall yield, with tri(1H-1,2,4-triazol-1-yl)phosphine oxide gave compound (6a) in high yield, and with 3-nitro-1,2,4-triazole and diphenyl phosphorochloridate it gave compound (6b) in high yield.When the former product (6a) was allowed to react with ammonia, methylamine, dimethylamine, and morpholine at room temperature, and the products further deacetylated if necessary, ara-C (1; R1=R2=H) and its corresponding 4-N-alkyl derivatives (1; R1=H, R2=Me), (1: R1=R2=Me), and 1,R2= -(CH2)2O(CH2)2-> were obtained in very high yields. 4-N-Phenyl-ara-C (1; R1=H, R2=Ph) was obtained in high yield when compound (6a) or (6b) was heated with aniline in pyridine solution and the products then deacetylated.The nitro-compound (6b) was converted into the ara-C derivative (1; R1=H, R2=CH2CO2Me), and the sulphide (7) was obtained following the deacetylation of the products of the reaction between the 1,2,4-triazolyl derivative (6a), toluene-p-thiol, and triethylamine.