125057-08-1

Basic information

• Product Name: 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)-4-thioxo-3,4-dihydropyrimidin-2(1H)-one
• Synonyms: 2(1H)-pyrimidinone, 3,4-dihydro-1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)-4-thioxo-
• CAS NO: 125057-08-1
• Molecular Formula: C₁₃H₁₄N₂O₃S₂
• Molecular Weight: 310.3919
• Mol File: 125057-08-1.mol

Chemical Properties

• Density: 1.45g/cm³
• Refractive Index: 1.703
• CAS DataBase Reference: 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)-4-thioxo-3,4-dihydropyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)-4-thioxo-3,4-dihydropyrimidin-2(1H)-one(125057-08-1)
• EPA Substance Registry System: 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)-4-thioxo-3,4-dihydropyrimidin-2(1H)-one(125057-08-1)

Safety Data

• Hazardous Substances Data: 125057-08-1(Hazardous Substances Data)

Usage

Chemical class

Pyrimidine derivative

Explanation

The compound is a derivative of the pyrimidine heterocycle, which is a six-membered nitrogen-containing ring.

Explanation

The thioxo group is a key structural feature of the compound, contributing to its chemical reactivity and potential biological activity.

Explanation

The hydroxyethyl group adds polarity and hydrogen bonding capability to the molecule, which can influence its solubility and interactions with other molecules.

Explanation

The phenylsulfanyl group introduces aromaticity and steric bulk to the molecule, which can affect its physical properties and potential interactions with biological targets.

Explanation

The compound's complex structure and biological activity suggest that it may have medicinal properties and could be used in the development of new drugs or as a research tool in the study of biological processes.

Explanation

The unique chemical structure of the compound makes it an interesting candidate for further research, potentially leading to the development of new drugs or the enhancement of its properties and functions for various applications.

Explanation

The compound exhibits biological activity, which is the basis for its potential pharmaceutical applications and further research.

Explanation

The synthesis and purification of the compound may involve multiple steps and require specific conditions to ensure the desired product is obtained with high purity, which is crucial for its potential applications and further study.

Thioxo group

A sulfur-oxygen double bond (C=S)

Hydroxyethyl group

An ethyl group with a hydroxyl (-OH) substituent

Phenylsulfanyl group

A phenyl group bonded to a sulfur atom

Upstream product

• 132885-37-1 1-<<2-(benzoyloxy)ethoxy>methyl>-6-(phenylthio)-4-thiouracil 
• 125057-25-2 1-<<2-(benzoyloxy)ethoxy>methyl>-6-(phenylthio)uracil 

Relevant articles and documents

Synthesis and anti-HIV activity of 2-, 3- and 4-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)

Several analogues of a new lead for anti-HIV-1 agents, 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT), in which the C-2, N-3, or C-4 position was modified were synthesized. These involve 2-thiothymine (11), 2-thiouracil (12), 4-thiothymine (17), 4-thiouracil (18), 5-methylcytosine (27), and cytosine (28) derivatives. Preparation of N-3-substituted derivatives (29 and 30) of HEPT was also carried out. Among these analogues, compound 11 exhibited excellent activity against HIV-1 HTLV-III(B) strain with an EC50 value of 0.98 μM, which is 7-fold more potent than that of HEPT. Removal of the 5-methyl group in compound 11 results in total loss of activity. Other compounds did not show any anti-HIV-1 activity. The 4-thio derivatives 17 and 18 were found to be rather cytotoxic. When compound 11 was evaluated for its inhibitory effects on another HIV-1 strain, HTLV-III(RE), and two HIV-2 strains, LAV-2(ROD) and LAV-2(EHO), it proved equally inhibitory to HTLV-III(RF), whereas both HIV-2 strains were insensitive to the compound.