199851-90-6

Basic information

• Product Name: 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one
• Synonyms: 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one
• CAS NO: 199851-90-6
• Molecular Weight: 274.387
• Mol File: 199851-90-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one(199851-90-6)
• EPA Substance Registry System: 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one(199851-90-6)

Safety Data

• Hazardous Substances Data: 199851-90-6(Hazardous Substances Data)

Upstream product

• 39101-54-7 3,5-dimethylphenylacetonitrile 
• 17356-08-0 thiourea 
• 176519-54-3 4-(3,5-Dimethyl-phenyl)-2-ethyl-3-oxo-butyric acid ethyl ester 

Downstream Products

• 199852-51-2 3-Allyl-2-allylsulfanyl-6-(3,5-dimethyl-benzyl)-5-ethyl-3H-pyrimidin-4-one 
• 261899-98-3 2-(7-bromo-3,5-dioxaheptylthio)-6-(3,5-dimethylbenzyl)-5-ethyl-pyrimidin-4(3H)-one 
• 199852-34-1 7-(3,5-Dimethyl-benzyl)-6-ethyl-3-methoxy-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one 
• 199852-35-2 7-(3,5-Dimethyl-benzyl)-3-ethoxy-6-ethyl-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one 
• 199852-21-6 5-(3,5-Dimethyl-benzyl)-6-ethyl-3-methoxy-2,3-dihydro-thiazolo[3,2-a]pyrimidin-7-one 
• 199852-36-3 7-(3,5-Dimethyl-benzyl)-6-ethyl-3-(2-hydroxy-ethoxy)-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one 
• 199852-23-8 5-(3,5-Dimethyl-benzyl)-3-ethoxy-6-ethyl-2,3-dihydro-thiazolo[3,2-a]pyrimidin-7-one 
• 199852-24-9 5-(3,5-Dimethyl-benzyl)-6-ethyl-3-(2-hydroxy-ethoxy)-2,3-dihydro-thiazolo[3,2-a]pyrimidin-7-one 
• 959635-11-1 6-(3,5-dimethylbenzyl)-5-ethyl-2-((4-methoxyphenyl)carbonylmethylthio)pyrimidin-4(3H)-one 
• 959635-13-3 6-(3,5-dimethylbenzyl)-5-ethyl-2-(phenylcarbonylmethylthio)pyrimidin-4(3H)-one 
• 1147724-24-0 6-(3,5-dimethylbenzyl)-5-ethyl-2-(4-methoxybenzylsulfanyl)-pyrimidin-4(3H)-one 
• 1147724-28-4 2-(benzylsulfanyl)-6-(3,5-dimethylbenzyl)-5-ethylpyrimidin-4(3H)-one 
• 1056025-54-7 6-(3,5-dimethylbenzyl)-5-ethyl-2-(methylthio)pyrimidine-4(1H)-one 

Relevant articles and documents

Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651

Novel emivirine analogues 6a, b were synthesized by reacting chloromethyl ethyl ether with 5-ethyl/isopropyl-6-(3,5-dimethoxybenzyl)uracils 5e, f. On the other hand, A series of new TNK-651 analogues 10a-f substituted at N-1 with phenoxyethoxymethyl moiety was prepared on treatment of the corresponding uracils 5a-f with bis(phenoxyethoxy)methane (9). The newly synthesized non-nucleosides were tested for antiviral activity against wild type HIV-1 IIIB as well as the resistant strains N119 (Y181C), A17 (K103N+Y181C), and the triple mutant EFVR (K103R+V179D+P225H) in MT-4 cells. Most of the tested compounds showed good activities. Among them 6-(3,5-dimethylbenzyl)-5-ethyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10c) and 6-(3,5-dimethylbenzyl)-5-isopropyl-1-[(2-phenoxyethyl)oxymethyl]uracil (10d) that showed inhibitory potency higher than emivirine against both wild type HIV-1 and the tested mutant strains, as well as higher activity than efavirenz against EFVR.

Synthesis of novel uracil non-nucleoside derivatives as potential reverse transcriptase inhibitors of HIV-1

Novel emivirine and TNK-651 analogues 5a-d were synthesized by reaction of chloromethyl ethyl ether and / or benzyl chloromethyl ether, respectively, with uracils having 5-ethyl and 6-(4-methylbenzyl) or 6-(3,4-dimethoxybenzyl) substituents. A series of new uracil non-nucleosides substituted at N-1 with cyclopropylmethyloxymethyl 9a-d, 2-phenylethyloxymethyl 9e-h, and 3-phenylprop-1-yloxymethyl 9i-l were prepared on treatment of the corresponding uracils with the appropriate acetals 8a-c. Some of the tested compounds showed good activity against HIV-1 wild type. Among them, 1-cyclopropylmethyloxymethyl- 5-ethyl-6-(3,5-dimethylbenzyl)uracil 9c and 5-ethyl-6-(3,5-dimethylbenzyl)-1-(2- phenylethyloxymethyl)uracil 9g showed inhibitory potency equally to emivirine against HIV-1 wild type. Furthermore, compounds 9c and 9g showed marginal better activity against NNRTI resistant mutants than emivirine.