137897-89-3

Basic information

• Product Name: 5-isopropyl-1-((hydroxyethoxy)methyl)-6-(3,5-dimethylphenythio)-2-thiouracil
• Synonyms: 5-isopropyl-1-((hydroxyethoxy)methyl)-6-(3,5-dimethylphenythio)-2-thiouracil
• CAS NO: 137897-89-3
• Molecular Formula: C₁₈H₂₄N₂O₃S₂
• Molecular Weight: 0
• Mol File: 137897-89-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.29g/cm³
• Refractive Index: 1.638
• CAS DataBase Reference: 5-isopropyl-1-((hydroxyethoxy)methyl)-6-(3,5-dimethylphenythio)-2-thiouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 5-isopropyl-1-((hydroxyethoxy)methyl)-6-(3,5-dimethylphenythio)-2-thiouracil(137897-89-3)
• EPA Substance Registry System: 5-isopropyl-1-((hydroxyethoxy)methyl)-6-(3,5-dimethylphenythio)-2-thiouracil(137897-89-3)

Safety Data

• Hazardous Substances Data: 137897-89-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H24N2O3S2/c1-11(2)15-16(22)19-18(24)20(10-23-6-5-21)17(15)25-14-8-12(3)7-13(4)9-14/h7-9,11,21H,5-6,10H2,1-4H3,(H,19,22,24)

Upstream product

• 65151-60-2 3,5,3',5'-tetramethyldiphenyldissulfide 
• 137897-85-9 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-5-isopropyl-2-thiouracil 

Downstream Products

• 137897-92-8 6-<(3,5-dimethylphenyl)thio>-5-isopropyl-1-<(2-hydroxyethoxy)methyl>uracil 

Relevant articles and documents

Pyrimidine nucleoside derivative and antiviral agent containing the derivative as active ingredient

A pyrimidine nucleoside derivative and pharmaceutically acceptable salt thereof specified by the presence of ethyl group or isopropyl group at 5-position of the pyrimidine ring and the presence of a (substituted) phenylthio or a (substituted) benzyl group

Structure-Activity Relationships of 1--6-(phenylthio)thymine Analogues: Effect of Substitutions at the C-6 Phenyl Ring and at the C-5 Position on Anti-HIV-1 Activity

The effect of substitution on the pyrimidine moiety of 1--6-(phenylthio)thymine (HEPT) and 1--6-(phenylthio)-2-thiothymine (HEPT-S) on anti-HIV-1 activity was investigated by synthesizing a series of 5-methyl-6-(arylthio) and 5-substituted-6-(phenylthio) derivatives.Preparation of the 5-methyl-6-(arylthio) derivatives was carried out based on either LDA lithiation of 1-methyl>thymine (3) and 1-methyl>-2-thiothymine (4) followed by reaction with diaryl disulfides or an addition-elimination reaction of 1-methyl>-6-(phenylsulfinyl)thymine (31) with aromatic thiols.Preparation of the 5-substituted-6-(phenylthio) derivatives was carried out based on either C-5 lithiation of the 1-methyl>-6-(phenylthio)uracil (41) with LTMP or the LDA lithiation of 5-alkyl-1-methyl>-2-thiouracil derivatives 45-47.Substitution at the meta position of the C-6-(phenylthio) ring by the methyl group improved the original anti-HIV-1 activity of HEPT, and introduction of two m-methyl groups to the phenylthio ring further potentiated the activity -1-thymine (28), 0.26 μM; 6--1--2-thiothymine (30), 0.22 μM>.When the 5-methyl group was replaced by an ethyl or an isopropyl group, the anti-HIV-1 activity of HEPT was also improved remarkably -6-(phenylthio)-2-thiouracil (48), 0.11 μM; 5-isopropyl-1--6-(phenylthio)-2-thiouracil (50), 0.059 μM; 5-ethyl-1--6-(phenylthio)-2-thiouracil (54), 0.12 μM; 5-isopropyl-1--6-(phenylthio)-2-thiouracil (56), 0.063 μM>. 6--5-ethyl-1-thymine derivatives 51 and 57 and 6--5-isopropyl-1-thymine derivatives 52 and 58 inhibited the replication of HIV-1 in the nanomolar concentration range.