5-Trifluoromethyl-2'-deoxycytidine

Base Information

• Chemical Name: 5-Trifluoromethyl-2'-deoxycytidine
• CAS No.: 66384-66-5
• Molecular Formula: C10H12F3N3O4
• Molecular Weight: 295.218
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60216605
• Nikkaji Number: J588.002E
• Wikidata: Q83092850
• ChEMBL ID: CHEMBL3220081
• Mol file: 66384-66-5.mol

Synonyms:2'-deoxy-5-trifluoromethylcytidine;5-trifluoromethyl-2'-deoxycytidine;TFMDC

Chemical Property of 5-Trifluoromethyl-2'-deoxycytidine

Chemical Property:

• Melting Point: 121 °C
• Boiling Point: 433 °C at 760 mmHg
• Flash Point: 215.7 °C
• PSA: 110.60000
• Density: 1.82 g/cm³
• LogP: 0.06620
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 295.07799036
• Heavy Atom Count: 20
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)C(F)(F)F)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)C(F)(F)F)CO)O
• General Description: 5-(Trifluoromethyl)-2'-deoxycytidine is a nucleoside analog structurally related to 2'-deoxy-5-trifluoromethyluridine (F3Thd), with potential antitumor properties. While the referenced study primarily focuses on acyl derivatives of F3Thd, it indirectly suggests that modifications to similar compounds, such as 5-(trifluoromethyl)-2'-deoxycytidine, could enhance their stability and therapeutic efficacy by resisting enzymatic degradation. The findings imply that acylated derivatives of such nucleosides may improve pharmacokinetics and antitumor activity, though specific data on 5-(trifluoromethyl)-2'-deoxycytidine itself were not detailed in the abstract.

Technology Process of 5-Trifluoromethyl-2'-deoxycytidine

There total 9 articles about 5-Trifluoromethyl-2'-deoxycytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.7%

C24H18Cl2F3N3O6 → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With methanol; sodium methylate; at -15 - -5 ℃; for 4h; Reagent/catalyst; Temperature;

Reference yield: 73.0%

sodium triflate (2926-30-9) + 2'-Deoxycytidine (951-77-9) → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With tert.-butylhydroperoxide; In water; at 0 - 20 ℃; for 3h;

DOI:10.1039/c3md00159h

Reference yield: 69.0%

3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine (76514-04-0) → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With ammonia; at 5 ℃;

DOI:10.1039/P19800002755

upstream raw materials:

3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine

5-iodo-4-acetamido-(2'-deoxy-3'-acetoxy-5'-acetoxymethyl)cytidine

N⁴-acetyl-1-<2'-deoxy-3',5'-di-O-acetyl-β-D-ribofyranosyl>cytosine

sodium triflate

Downstream raw materials:

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

Refernces

Studies on antitumor agents. VI. Syntheses and antitumor activities of acyl derivatives of 2'-deoxy-5-trifluoromethyluridine.

10.1248/cpb.35.2090

The study investigates the synthesis and antitumor activities of various acyl derivatives of 2'-deoxy-5-trifluoromethyluridine (F3Thd) and 2'-deoxy-5-trifluoromethylcytidine. F3Thd, first synthesized in 1962, has significant biological activities but suffers from a short half-life in plasma due to rapid degradation by thymidine phosphorylase. To address this, acyl derivatives including 5'-O-acyl, 3',5'-di-O-acyl, N3-acyl, 3',5'-di-O-carbamoyl, and 3',5'-di-O-ethoxycarbonyl compounds were synthesized. These derivatives were tested for their antitumor effects against sarcoma 180 in mice through oral administration. The results showed that the 5'-O-hexanoyl compound of F3Thd exhibited the highest activity, with an ED50 value one-third that of F3Thd. Full protection of the sugar moiety with aroyl or carbamoyl groups significantly decreased activity. N3-benzoyl compounds were slightly more effective than F3Thd, but none surpassed the effective O-acyl compounds. The study highlights the potential of these acyl derivatives to enhance the antitumor activity of F3Thd by resisting degradation and maintaining higher plasma concentrations.

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