93080-09-2

Basic information

• Product Name: 1-(4-Thio-beta-D-ribofuranosyl)cytosine
• Synonyms: 1-(4-Thio-beta-D-ribofuranosyl)cytosine;4'-Thiocytidine
• CAS NO: 93080-09-2
• Molecular Formula: C9H13N3O4S
• Molecular Weight: 259.28222
• Mol File: 93080-09-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-Thio-beta-D-ribofuranosyl)cytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Thio-beta-D-ribofuranosyl)cytosine(93080-09-2)
• EPA Substance Registry System: 1-(4-Thio-beta-D-ribofuranosyl)cytosine(93080-09-2)

Safety Data

• Hazardous Substances Data: 93080-09-2(Hazardous Substances Data)

Usage

Chemical class

Modified nucleoside, sulfur-containing nucleoside analog

Antineoplastic activity

Potential antineoplastic activity

Cancer treatment

Used in the treatment of acute myeloid leukemia, chronic myelogenous leukemia, and myelodysplastic syndrome

Mechanism of action

Inhibits DNA and RNA synthesis, disrupting cancer cell proliferation and causing cell death

Administration

Can be administered orally or intravenously

Ongoing research

Being studied for potential use in combination with other chemotherapy agents and for treatment of other malignancies

Upstream product

• 161424-51-7 1-<2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl>-N₄-benzoyl-cytosine 
• 161424-56-2 1-(2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl)-4-thio-uracil 
• 161512-40-9 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-D-ribofuranose 
• 144950-26-5 2,3,5-tri-O-benzyl-L-lyxose dibenzyldithioacetal 
• 153439-75-9 2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal 
• 158852-11-0 benzyl 2,3,5-tri-O-benzyl-1,4-dithio-D-ribofuranoside 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 
• 291758-17-3 N⁴-acetyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine 
• 869347-03-5 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol 
• 159981-07-4 N⁴-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine 

Relevant articles and documents

Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues

Analogues of the canonical nucleosides required for nucleic acid synthesis have a longstanding presence and proven capability within antiviral and anticancer research. 4′-Thionucleosides, that incorporate bioisosteric replacement of furanose oxygen with sulfur, represent an important chemotype within this field. Established herein is synthetic capability towards a common 4-thioribose building block that enables access to thio-ribo and thio-arabino pyrimidine nucleosides, alongside their 4′-sulfinyl derivatives. In addition, this building block methodology is templated to deliver 4′-thio and 4′-sulfinyl analogues of the established anticancer drug gemcitabine. Cytotoxic capability of these new analogues is evaluated against human pancreatic cancer and human primary glioblastoma cell lines, with observed activities ranging from low μM to >200 μM; explanation for this reduced activity, compared to established nucleoside analogues, is yet unclear. Access to these chemotypes, with thiohemiaminal linkages, will enable a wider exploration of purine and triphosphate analogues and the application of such materials for potential resistance towards relevant hydrolytic enzymes within nucleic acid biochemistries.

A practical synthesis of 4′-thioribonucleosides

A practical synthesis of 4′-thioribonucleosides starting from inexpensive l-arabinose is described. 1,4-Anhydro-2,3-O-isopropylidene-4- thioribitol, which was prepared by using a novel reductive ring-contraction reaction, was converted to the 5-O-silylated sulfoxides. The Pummerer-type thioglycosylation of the sulfoxides gave the 4′-thioribonucleosides stereoselectively.

The stereoselective synthesis of 4'-β-thioribonucleosides via the pummerer reaction

An efficient stereoselective synthesis of 4'-β-thioribonucleosides 14, 15, 27, and 30 using the Pummerer reaction as the key step is described. The Pummerer reaction of 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopro pyldisiloxane-1,3-di