42039-81-6

Basic information

• Product Name: 5-ethyldihydro-2-thioxopyrimidine-4,6(1H,5H)-dione
• Synonyms: 5-ethyldihydro-2-thioxopyrimidine-4,6(1H,5H)-dione;5-Ethyldihydro-2-thioxo-4,6(1H,5H)-pyrimidinedione
• CAS NO: 42039-81-6
• Molecular Formula: C₆H₈N₂O₂S
• Molecular Weight: 172.20492
• EINECS: 255-636-3
• Mol File: 42039-81-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.37g/cm³
• Refractive Index: 1.593
• CAS DataBase Reference: 5-ethyldihydro-2-thioxopyrimidine-4,6(1H,5H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethyldihydro-2-thioxopyrimidine-4,6(1H,5H)-dione(42039-81-6)
• EPA Substance Registry System: 5-ethyldihydro-2-thioxopyrimidine-4,6(1H,5H)-dione(42039-81-6)

Safety Data

• Hazardous Substances Data: 42039-81-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H8N2O2S/c1-2-3-4(9)7-6(11)8-5(3)10/h3H,2H2,1H3,(H2,7,8,9,10,11)

Upstream product

• 17356-08-0 thiourea 
• 133-13-1 ethyl diethyl malonate 
• 7664-93-9 sulfuric acid 
• 857586-10-8 5-ethyl-5-benzyl-2-thio-barbituric acid 

Downstream Products

• 875094-81-8 5-ethyl-2-[(2,4-difluorophenacyl)thio]-4,6-di(p-tolylsulfonyloxy)pyrimidine 
• 875094-37-4 5-ethyl-2-[(4-methoxyphenacyl)thio]-4,6-di(p-tolylsulfonyloxy)pyrimidine 
• 875094-40-9 5-ethyl-2-[(4-fluorophenacyl)thio]-4,6-di(p-tolylsulfonyloxy)pyrimidine 
• 875094-31-8 5-ethyl-2-(phenacyl)thio-4,6-di(p-tolylsulfonyloxy)pyrimidine 

Relevant articles and documents

Synthesis and biological evaluation of new conformationally restricted S-DABO hybrids as non-nucleoside inhibitors of HIV-1 reverse transcriptase

A series of conformationally restricted dihydro-alkylthio-benzyl- oxopyrimidine (S-DABO) hybrids, which combined the structural features of C6-α-methylbenzyl-thio-DABOs (α-methyl-S-DABOs) and C6-α-cyanobenzyl-thio-DABOs (CN-S-DABOs), has been synthesized and biologically evaluated for their anti-HIV activity against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056 and HIV-2 strain ROD in MT-4 cell cultures. Most of these compounds exhibited inhibitory activity (wild-type) within the range of EC50 values from micromolar to nanomolar. Among them, compound 1s displayed the highest anti-HIV-1 activity with an EC50 value of 91 nM and a selectivity index (SI) of 548, which was more potent than zalcitabine and comparable to nevirapine and delavirdine in the same assay. The HIV-1 reverse transcriptase inhibitory (RT) assay confirmed that these conformationally restricted S-DABO hybrids targeted HIV-1 RT. The preliminary structure-activity relationship (SAR) and molecular docking analysis of this new series of conformationally constrained CN-S-DABO hybrids were also investigated.

Synthesis and anti-HIV-1 activity evaluation of 5-alkyl-2-alkylthio-6- (arylcarbonyl or α-cyanoarylmethyl)-3,4-dihydropyrimidin-4(3H)-ones as novel non-nucleoside HIV-1 reverse transcriptase inhibitors

A series of novel S-DABO analogues (S-DABOs, 1) were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Key structural modifications included replacement of the 6-arylmethyl group by a 6-arylcarbonyl or 6-(α-cyanoarylmethyl) group. Most of the compounds showed only micromolar potency against HIV-1 in MT-4 cells in vitro, though two of them (3e and 3g) were unusually potent (IC50 = 0.09 and 0.002 μM, respectively) and selective (SI = 1500 and 4600, respectively). Structure-activity relationships among the newly synthesized S-DABOs are discussed.