134111-32-3

Basic information

• Product Name: 2'-deoxy-4'-thiouridine
• Synonyms: 2'-deoxy-4'-thiouridine
• CAS NO: 134111-32-3
• Molecular Formula: C₉H₁₂N₂O₄S
• Molecular Weight: 244.26758
• Mol File: 134111-32-3.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.553g/cm³
• CAS DataBase Reference: 2'-deoxy-4'-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxy-4'-thiouridine(134111-32-3)
• EPA Substance Registry System: 2'-deoxy-4'-thiouridine(134111-32-3)

Safety Data

• Hazardous Substances Data: 134111-32-3(Hazardous Substances Data)

Upstream product

• 209048-61-3 1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol 
• 160452-65-3 1-[3,5-di-O-acetyl-2-deoxy-4-thio-β-D-ribofuranosyl]uracil 
• 166249-05-4 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]uracil 
• 169736-17-8 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose 
• 138560-15-3 1-<5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-β-D-erythro-pemtofuranosyl>uracil 
• 148556-03-0 5-O-acetyl-3-O-tert-butyldimethylsilyl-2-deoxy-4-thio-D-erythro-pentofuranoside 
• 134700-26-8 1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose 
• 134938-97-9 benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 
• 219613-62-4 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione 
• 166812-96-0 3',5'-di-O-benzyl-4'-thio-2'-deoxyuridine 
• 166812-97-1 3-Benzoyl-1-((2R,4S,5R)-4-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione 
• 138560-08-4 1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil 
• 134111-27-6 1-(2-deoxy-4-thio-3,5-di-O-toluoyl-β-D-erythro-pentofuranosyl)uracil 

Downstream Products

• 66-22-8 uracil 
• 166813-01-0 1-(5-O-trityl-2-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil 
• 166812-98-2 1-((2R,4R,5R)-4-Fluoro-5-trityloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Synthesis of 4′-substituted 2′-deoxy-4′-thiocytidines and its evaluation for antineoplastic and antiviral activities

4′-Azido- (7), 4′-C-fluoromethyl- (8) 4′-C-ethynyl- (9) and 4′-C-cyano- (10) 2′-deoxy-4′-thiocytidines have been synthesized. In this study, it was found that the isolated yield of 4′-thiouracil nucleoside 13 in a Lewis acid-promoted Vorbrüggen-type glycosidation utilizing 12 was better than that of the electrophilic glycosidation reaction between silylated uracil and 11. This improved result prompted us to perform the glycosidation utilizing 36 and 43 for the synthesis of 37 and 44. Introduction of the azido group was carried out by nucleophilic substitution in the 4′-benzoyloxy derivative 22a. On the other hand, 9 and 10 were synthesized by way of the chemical manipulation of the hydroxymethyl group at the 4′-position of 46. Evaluation of the antineoplastic activity of 2 and 7–10 against human B-cell (CCRF-SB) and T-cell leukemia (Molt-4) cell lines revealed that 4′-azido- (7) and 4′-C-fluoromethyl- (8) derivatives exhibited cytotoxic activity whereas no cytotoxicity was observed in the 4′-C-ethynyl- (9) and 4′-C-cyano- (10) derivatives as well as the parent compound 2. Compound 7 was also found to possess promising antiviral activity against VZV and HSV-1 without any cytotoxity against HEL host cells. It is noteworthy that 7 exhibited potent inhibitory activities against the thymidine kinase-deficient (TK?) mutant of VZV and HSV-1.

Synthesis and hydrolytic stability of the α and β anomers of 4′-thio-2′-deoxyuridine and their 5-substituted analogs. Competition between the acid-catalysed depyrimidination and isomerisation to a 5-thiopyranoside nucleoside

The α and β anomers of 4′-thio-2′-deoxyuridine were readily synthesised as an anomeric mixture using adapted methodology and separated chromatographically as their 3′,5′-di-O-benzyl-N3-benzoyl derivatives. The 5-fluoro analogs were prepared in a similar manner, but the anomers could be separated simply as their 3,5-di-O-benzyl derivatives. The kinetics of acid-catalysed hydrolysis for the four compounds and their 5-alkylated analogs are reported. Under these conditions, cleavage of the N-glycosidic bond competes with the reversible isomerisation between the furano (4′-thio) and pyrano (5′-thio) ring systems. This was confirmed by isolation and NMR characterisation of the α and β pyranose intermediates of the parent compounds.

2'-deoxy-4'-thioribonucleosides and their antiviral activity

2'-Deoxy-4'-thio-ribonucleosides, intermediates in their production, and their use as antiviral and anticancer agents are disclosed.

The synthesis and biological activity of certain 4'-thionucleosides

Results are presented on the synthesis and biological activity of several types of 4'-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4'-thiothymidine are also presented.

Syntheses and antitumor activities of D- and L-2'-deoxy-4'-thio pyrimidine nucleosides

Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio- β-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L- enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4- thio-α,β-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with "up" hydroxyl groups

Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-β-D-threo- pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were con

Synthesis and Biological Activity of 2'-Deoxy-4'-thio Pyrimidine Nucleosides

2'-Deoxy-4'-thiocytidine (7β), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro.All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also act