7236-57-9

Basic information

• Product Name: Thymidine, 4-thio-
• Synonyms: Thymidine, 4-thio-;deoxy-4-thiothymidine;3,4-Dihydro-5-methyl-1-(2-deoxy-β-D-ribofuranosyl)-4-thioxopyrimidin-2(1H)-one;1-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-methyl-4-thioxo-3,4-dihydropyrimidin-2(1H)-one;4-Thiothymidin
• CAS NO: 7236-57-9
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29416
• Mol File: 7236-57-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.52g/cm³
• Refractive Index: 1.672
• CAS DataBase Reference: Thymidine, 4-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 4-thio-(7236-57-9)
• EPA Substance Registry System: Thymidine, 4-thio-(7236-57-9)

Safety Data

• Hazardous Substances Data: 7236-57-9(Hazardous Substances Data)

Usage

General Description

4-thio-thymidine is a chemical analog of the nucleoside, thymidine, which is commonly found in DNA. Thymidine, 4-thio- has a sulfur atom replacing an oxygen atom in the thymidine molecule, which gives it unique photo-reactive properties. It is often used in research as a molecular probe to study the dynamics of DNA and RNA due to its ability to form covalent bonds upon exposure to UV light. It is efficiently incorporated into DNA and its absorbance and fluorescence properties enable it to be tracked and visualized in biological systems.

InChI:InChI=1/C10H14N2O4S/c1-5-3-12(10(15)11-9(5)17)8-2-6(14)7(4-13)16-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,17)/t6-,7+,8+/m0/s1

Upstream product

• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 6979-97-1 3',5'-diacetylthymidine 
• 20188-74-3 3',5'-di-O-acetyl-4-thiothymidine 
• 10457-18-8 3',5'-bis-O-(trimethylsilyl)-thymidine 
• 50-89-5 thymidine 
• 189005-86-5 4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 
• 82913-18-6 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-4-thioxo-3,4-dihydro-1H-pyrimidin-2-one 
• 93841-35-1 O^3'_,O5'-dibenzoyl-4-thio-thymidine 
• 35898-30-7 3',5'-di-O-benzoylthymidine 

Downstream Products

• 103388-15-4 di-thymidin-4-yl disulfide 
• 50-89-5 thymidine 
• 27089-40-3 1-((2R,4S,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-4-thioxo-3,4-dihydro-1H-pyrimidin-2-one 
• 108584-96-9 6-(2-Deoxy-β-D-ribosyl)-8-methyltetrazolo<1,5-c>pyrimidin-5(6H)-one 
• 122567-96-8 Methanesulfonic acid (2R,3R,5R)-5-(5-methyl-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 108441-45-8 3'-azido-3'-deoxy-4-thio-β-D-thymidine 
• 125258-56-2 5'-O-(4,4'-Dimethoxytrityl)-4-thiothymidine 
• 1053261-63-4 C₄₉H₅₇N₄O₁₆PS 
• 1053715-58-4 C₄₉H₅₇N₄O₁₆PS 

Relevant articles and documents

4 - Thiodeoxythymidine derivative and anti-hepatitis B virus pharmaceutical application thereof

4 - Thio-deoxythymidine derivatives and anti-hepatitis B virus pharmaceutical applications thereof are disclosed. The invention provides 4 - thiodeoxythymidine derivative or a pharmaceutically acceptable salt thereof, and the structure is shown in structural formula I or structural formula II. An in-vitro cytotoxicity test and an in-vitro anti HBV virus pharmacodynamic test proves 4 - thiodeoxythymidine derivative or a pharmaceutically acceptable salt thereof has anti HBV activity, has an anti-hepatitis B drug development prospect and provides a potential choice for treating viral hepatitis.

Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides

Unambiguous characterization of 5-substituted-4-thiopyrimidine nucleosides (ribonucleosides and 2'-deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5-bromo-4-thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4-thiopyrimidine nucleosides are compared, and the key contributing factors discussed. The approach presented here is applicable to other modified nucleosides and nucleotides, as well as nucleobases. Copyright

Convenient intermediates for the preparation of C-4 modified derivatives of pyrimidine nucleosides

4-(4-Nitrophenoxy)-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5- methyl-4-(1,2,4-triazol-1-yl)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)- one 7a and 4-(4-nitrophenoxy)-1-(βD-2-deoxyribofuranosyl)pyrimidin-2(1H)- one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.