66335-38-4

Basic information

• Product Name: 5'-Deoxy-5-fluorocytidine
• Synonyms: 5'-DEOXY-5-FLUOROCYTIDINE;5-FLUORO-5'-DEOXYCYTIDINE;5'-DFCR;5'-Deoxy-5-fluoro-D-cytidine;5''-DEOXY-5-FLUOROCYTIDINE (5''-DFCR);5-Fluoro-5’-deoxycytidine, 5’-DFCR;Capecitabine Related Compound A (10 mg) (5'-deoxy-5-fluorocytidine);Deoxy-5-fluorocytidine-D2
• CAS NO: 66335-38-4
• Molecular Formula: C₉H₁₂FN₃O₄
• Molecular Weight: 245.21
• EINECS: 1806241-263-5
• Product Categories: Bases & Related Reagents;Nucleotides;Heterocycles
• Mol File: 66335-38-4.mol

Chemical Properties

• Melting Point: 196-198°C
• Boiling Point: 437.874 °C at 760 mmHg
• Flash Point: 218.619 °C
• Appearance: White solid
• Density: 1.841 g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.65±0.70(Predicted)
• Stability: HYGROSCOPIC
• CAS DataBase Reference: 5'-Deoxy-5-fluorocytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Deoxy-5-fluorocytidine(66335-38-4)
• EPA Substance Registry System: 5'-Deoxy-5-fluorocytidine(66335-38-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39-24/25
• Hazardous Substances Data: 66335-38-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 933444-01-0 C₉H₁₁FN₂O₄S 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 66335-37-3 5'-deoxy-2',3'-O-isopropylidene-5-fluorocytidine 
• 154361-50-9 capecitabine 
• 124012-42-6 5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine 

Downstream Products

• 162204-35-5 N₄-(cyclohexyloxycarbonyl)-5'-deoxy-5-fluorocytidine 
• 154361-50-9 capecitabine 
• 161599-46-8 (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate 
• 124012-64-2 3'-O-benzoyl-5'-deoxy-5-fluorocytidine 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR THE TREATMENT OF CANCER

The invention relates to the compounds or its pharmaceutical acceptable polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II, formula III, formula IV, formula V, formula VI, formula VII and formula VIII and, the methods for the treatment of cancer and infectious diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, lozenge, spray, intravenous, oral solution, buccal mucosal layer tablet, parenteral administration, syrup, or injection. Such compositions may be used to treatment of cancer, neoplasm, infections and skin diseases.

NOVEL SYNTHESIS OF 5-DEOXY-5'-FLUOROCYTIDINE COMPOUNDS

This invention relates to a process of synthesizing a β-nucleoside compound of formula (I): wherein R1 is alkyl, aryl, cycloalkyl, heteroaryl, or heterocycloalkyl. The process includes reacting a compound of formula (II): with a compound of formula (III): wherein R1 is as defined above and X is chloride, bromide, iodide, methanesulfonate, triflate, p-toluenesulfonate, trifluoroacetate, 4-nitrophenoxy, or N-succinimidyloxy, in a solvent and in the presence of a base.

Design, synthesis and anti-tumoractivity of novel amidine derivatives of doxifluridine

A series of novel amidine derivatives of doxifluridine were synthesized using acid amide as the starting material, and their anti-tumor activity was evaluated in A549 cells. Compounds 10 and 11 demonstrated were more potent than 5-Fu, which was used as a positive control. Compound 10, which were found to be the most potent one with IC50 of 3.2 μmol/L, was 16 times more potent than 5-Fu with IC50 of 52 μM to the A549 cells. A new route was designed to synthesize 5′-deoxy-5-fluorocytidine. All compounds were characterized by 1H NMR, MS and X-ray spectras in detail.

Process for the preparation of capecitabine

The present application relates to an improved process for the preparation of capecitabine.

MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates

Erbium(III) trifluoromethane sulfonate is proposed as a very gentle Lewis acid catalyst in a MW-assisted chemoselective method for the cleavage of isopropylidene acetals in awkward substrates by using pure water as the solvent.

BIOREDUCTIVELY-ACTIVATED PRODRUGS

The present invention relates to a compound of formula (1), or a pharmaceutically acceptable salt thereof, Formula: (1); wherein: R1 is a substituted aryl or heteroaryl group bearing at least one nitro or azido group or is an optionally substituted benzoquinone, optionally substituted naphthoquinone or optionally substituted fused heterocycloquinone; R2 is H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, aryl or heteroaryl; and R3 is selected such that R3NH2 represents a cytotoxic nucleoside analogue or an ester or phosphate ester prodrug of a cytotoxic nucleoside analogue, with the proviso that if R1 is an aryl group then R2 is not H.

Stability and degradation kinetics of 5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine in aqueous solution

The stability of 5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine (Ro 09-1390) in buffered solutions at 37 °C was studied. Seven degradation products were identified by high-performance liquid chromatography (HPLC) and spectroscopy. The degradation products were different depending on the pH of the solution. Ro 09-1390 was unstable at pH 2.1 and stable at around pH 5.6 in spite of forming several decomposition products; and its degradation rate did not change in the pH range from 8 to 12. The degradation of Ro 09-1390 followed apparent first order kinetics and the decomposition pathway at alkaline conditions was different from the one at acidic conditions. On the other hand, at neutral pH the other decomposition products were formed.

5'-Deoxy-5-fluoropyrimidine nucleosides

Novel 5'-deoxy-5-fluoropyrimidine nucleosides are potent anti-tumor agents. Preferred compounds are 5'-deoxy-5-fluorocytidine and 5'-deoxy-5-fluorouridine.