137897-76-8

Basic information

• Product Name: 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<(3-carboxyphenyl)thio>thymine
• Synonyms: 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<(3-carboxyphenyl)thio>thymine
• CAS NO: 137897-76-8
• Molecular Weight: 466.63
• Mol File: 137897-76-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<(3-carboxyphenyl)thio>thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<(3-carboxyphenyl)thio>thymine(137897-76-8)
• EPA Substance Registry System: 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<(3-carboxyphenyl)thio>thymine(137897-76-8)

Safety Data

• Hazardous Substances Data: 137897-76-8(Hazardous Substances Data)

Upstream product

• 125057-12-7 1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylsulfinyl)thymine 
• 72886-42-1 methyl 3-sulfanylbenzoate 
• 137915-51-6 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-<<3-(methoxycarbonyl)phenyl>thio>thymine 

Downstream Products

• 137897-79-1 1-<(2-acetoxyethoxy)methyl>-6-<(3-carbamoylphenyl)thio>thymine 
• 137897-78-0 6-<(3-carbamoylphenyl)thio>-1-<(2-hydroxyethoxy)methyl>thymine 
• 137897-80-4 6-<(3-cyanophenyl)thio>-1-<(2-hydroxyethoxy)methyl>thymine 
• 137897-77-9 6-<(3-carboxyphenyl)thio>-1-<(2-hydroxyethoxy)methyl>thymine 

Relevant articles and documents

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.