66384-66-5

Basic information

• Product Name: 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE
• Synonyms: 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE;5-(Trifluoromethyl)-2'-deoxycytidine97%;2'-deoxy-5-(trifluoromethyl)Cytidine
• CAS NO: 66384-66-5
• Molecular Formula: C₁₀H₁₂F₃N₃O₄
• Molecular Weight: 295.22
• Mol File: 66384-66-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 121°C
• Boiling Point: 433 °C at 760 mmHg
• Flash Point: 215.7 °C
• Appearance: /
• Density: 1.82 g/cm³
• CAS DataBase Reference: 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE(66384-66-5)
• EPA Substance Registry System: 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE(66384-66-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 66384-66-5(Hazardous Substances Data)

Usage

General Description

5-(Trifluoromethyl)-2'-deoxycytidine is a synthetic nucleoside analogue that has shown potential as an antiviral and anticancer agent. It is an analog of cytidine with a trifluspecifcifc modification at the 5-position, which makes it resistant to degradation by cellular enzymes. This chemical has been studied for its potential to inhibit the replication of certain viruses, including hepatitis C virus and HIV. Additionally, it has been investigated for its ability to inhibit the growth of cancer cells. Overall, 5-(Trifluoromethyl)-2'-deoxycytidine shows promise as a therapeutic agent for treating viral infections and cancer.

Upstream product

• 76514-04-0 3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine 
• 76514-03-9 5-iodo-4-acetamido-(2'-deoxy-3'-acetoxy-5'-acetoxymethyl)cytidine 
• 61671-83-8 N⁴-acetyl-1-<2'-deoxy-3',5'-di-O-acetyl-β-D-ribofyranosyl>cytosine 
• 2926-30-9 sodium triflate 
• 951-77-9 2'-Deoxycytidine 
• 2926-29-6 Langlois reagent 
• 54-20-6 5-trifluoromethyluracil 
• 7057-43-4 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine 

Downstream Products

• 97219-11-9 Benzoic acid (2R,3S,5R)-5-(4-amino-2-oxo-5-trifluoromethyl-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 

Relevant articles and documents

Preparation method of high-purity antineoplastic drug triflucytidine

The invention discloses a preparation method of a high-purity antineoplastic drug triflucytidine, which comprises the following steps: 1) obtaining 2,6-bis(trimethylsilyl-5-trifluoromethylpyrimidine) from 5-(trifluoromethyl)uracil and hexamethyldisilazane under the action of trimethylchlorosilane; 2) carrying out condensation reaction on the 2, 6-bis(trimethylsilyl-5-trifluoromethylpyrimidine) and the 3',5'-p-chlorobenzoyl-2'-deoxy-1-chloro-D-ribofuranose, and carrying out recrystallization to obtain 3', 5'- p-chlorobenzoyl-2'-deoxy-5-trifluoromethyl uridine; (3) carrying out reaction on the 3',5'-p-chlorobenzoyl-2'-deoxy-5-trifluoromethyl uridine and trifluoromethanesulfonic anhydride, and carrying out nucleophilic substitution by using ammonia, so as to obtain 3',5'-p-chlorobenzoyl-2'-deoxy-5-trifluoromethyl cytidine; and 4) carrying out deprotection on the 3',5'-p-chlorobenzoyl-2'-deoxy-5-trifluoromethyl cytidine under the action of sodium methoxide, and filtering and washing to obtain the triflucytidine. The preparation method of the high-purity antineoplastic drug triflucytidine disclosed by the invention is convenient for industrial preparation.

Trifluoromethyl derivatives of canonical nucleosides: Synthesis and bioactivity studies

The use of the system CF3SO2Na/tert-butyl- hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2′- deoxycytidine, 8-CF3-2′-deoxyadenosine, 8-CF 3-2′-deoxyguanosine and 8-CF3-inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-2′-deoxyguanosine and 8-CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.