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

Description

5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE is a synthetic nucleoside analogue that exhibits potential as an antiviral and anticancer agent. It is an analog of cytidine with a specific trifluoro modification at the 5-position, which confers resistance to degradation by cellular enzymes. This chemical has been studied for its capacity to inhibit the replication of certain viruses and the growth of cancer cells, making it a promising therapeutic agent for treating viral infections and cancer.

Uses

Used in Antiviral Applications:
5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE is used as an antiviral agent for its potential to inhibit the replication of specific viruses, such as hepatitis C virus and HIV. Its resistance to degradation by cellular enzymes enhances its effectiveness in combating viral infections.
Used in Anticancer Applications:
In the field of oncology, 5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE is used as an anticancer agent due to its ability to inhibit the growth of cancer cells. This property makes it a candidate for further research and development in cancer treatment strategies.
Used in Pharmaceutical Industry:
5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE is used as a key compound in drug development for its potential therapeutic applications in treating viral infections and various types of cancer, highlighting its importance in the pharmaceutical industry for creating novel treatment options.

Upstream product

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

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.