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

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

• 76514-04-0 3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine 
• 2926-30-9 sodium triflate 
• 951-77-9 2'-Deoxycytidine 
• 2926-29-6 Langlois reagent 
• 7057-43-4 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine 
• 54-20-6 5-trifluoromethyluracil 
• 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 

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.

Triplex- and duplex-forming abilities of oligonucleotides containing 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine

A facile synthesis of 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine phosphoramidites from commercially available 2′-deoxyuridine and 2′-deoxycytidine was achieved, respectively. The obtained phosphoramidites were incorporated into oligonucleotides, and their binding affinity to double-stranded DNA (dsDNA) and single-stranded RNA (ssRNA) was evaluated by UV-melting experiments. The triplex-forming abilities of oligonucleotides including 5-trifluoromethylpyrimidine nucleobases with dsDNA were decreased. Especially, the stability of the triplex containing a trifluoromethylcytosine (CF3C)-GC base triplet was low, likely due to the low pKa of protonated CF3C by the electron-withdrawing trifluoromethyl group. A slight decrease in stability of the duplex formed with ssRNA by oligonucleotides including 5-tri-fluoromethylpyrimidine nucleobases was only observed, suggesting that they might be applicable to various ssRNA-targeted technologies using features of fluorine atoms.

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.

Studies on Organic Fluorine Compounds. Part 35. Trifluoromethylation of Pyrimidine- and Purine-nucleosides with Trifluoromethyl-Copper Complex

Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl-copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder.The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine, -deoxycytidine, and arabinosylcytosine; 8-trifluoromethyl-adenosine, -deoxyadenosine, and -inosine; and 6-trifluoromethylribofuranosylpurine.This procedure offers simple synthesis of many trifluoromethyl compounds.