132885-31-5

Usage

Chemical class

Thioxo-pyrimidinone derivative
It belongs to a class of compounds derived from pyrimidinones, which are heterocyclic compounds with a six-membered ring containing four carbon and two nitrogen atoms, and a sulfur atom replacing one of the oxygen atoms.

Synthesis

Prepared through the reaction of ethyl 2-chloro-2-(hydroxymethyl)acetoacetate with thiourea
The compound is synthesized by reacting a specific chloroacetate ester with thiourea, a common reagent in the synthesis of thioxo-pyrimidinones.

Potential biological activity

Of interest in medicinal chemistry research
1-(2-HYDROXY-ETHOXYMETHYL)-2-THIOXO-2,3-DIHYDRO-1H-PYRIMIDIN-4-ONE may exhibit biological activities that could be useful in the development of new pharmaceuticals.

Applications

Development of new pharmaceuticals for treating various medical conditions
The compound may have potential applications in the treatment of different medical conditions, but further research is needed to explore its full range of properties and uses.

Further research

Necessary to understand its full range of properties and potential uses
More studies are required to fully comprehend the compound's characteristics, effectiveness, and safety profile before it can be considered for pharmaceutical applications.

Upstream product

• 646-06-0 1,3-DIOXOLANE 
• 32865-74-0 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine 
• 116457-79-5 1-(2-acetoxyethoxy methyl)-2-thiouracil 

Relevant academic research and scientific papers

Inhibition of hepatitis B virus (HBV) replication by pyrimidines bearing an acyclic moiety: Effect on wild-type and mutant HBV

Chronic hepatitis B virus (HBV) infection remains a major health problem worldwide. The main clinical limitation of a current antiviral drug for HBV, lamivudine, is the emergence of drug-resistant viral strains upon prolonged therapy. A group of 5-, 6-, or 5,6-substituted acyclic pyrimidine nucleosides with a 1-[(2-hydroxyethoxy)methyl] moiety were synthesized and evaluated for antiviral activities. The target compounds were prepared by the reaction of silylated uracils possessing a variety of substituents at the C-5 or C-6 positions or both with 1,3-dioxolane in the presence of potassium iodide and chlorotrimethylsilane by a convenient and single-step synthesis. Among the compounds tested, 5-chloro and 5-bromo analogues possessing an acyclic glycosyl moiety were the most effective and selective antiviral agents in the in vitro assays against wild-type duck HBV (EC50 = 0.4-2.2 and 3.7-18.5 μM, respectively) and human HBV-containing 2.2.15 cells (EC50 = 4.5-45.4 and 18.5-37.7 μM, respectively). These compounds were also found to retain sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and double mutations (L180M/M204V). The compounds investigated did not show cytotoxicity to host HepG2 and Vero cells, up to the highest concentration tested. The results presented here confirm and accentuate the potential of acyclic pyrimidine nucleosides as anti-HBV agents and extend our previous observations. We herein report the capability of acyclic pyrimidine nucleosides to inhibit the replication of both wild-type and drug-resistant mutant HBV.

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.