3094-09-5

Basic information

• Product Name: 5'-Deoxy-5-fluorouridine
• Synonyms: 5’-deoxy-5-fluoro-uridin;flutron;furtulon;RO-21-9738;(+)-5-FLUORO-5'-DEOXYURIDINE;5-FLUORO-5'-DEOXYURIDINE;5'-DEOXY-5-FLUOROURIDINE;5'-DEOXYFLUOROURIDINE
• CAS NO: 3094-09-5
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.19
• EINECS: 221-440-1
• Product Categories: Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Pyrazines, Pyrimidines & Pyridazines;API intermediates;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Intermediates & Fine Chemicals;Pharmaceuticals;Pyrazines, Pyrimidines & Pyridazines;Amines, Heterocycles, Metabolites & Impurities, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals;FURTULON;Anti-cancer&immunity;API
• Mol File: 3094-09-5.mol

Chemical Properties

• Melting Point: 188-192 °C(lit.)
• Appearance: White solid
• Density: 1.3751 (estimate)
• Refractive Index: 20 ° (C=1, H2O)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.4(at 25℃)
• Merck: 14,3437
• CAS DataBase Reference: 5'-Deoxy-5-fluorouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-Deoxy-5-fluorouridine(3094-09-5)
• EPA Substance Registry System: 5'-Deoxy-5-fluorouridine(3094-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 2
• RTECS: YU7526000
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 3094-09-5(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Doxifluridine is used as an antineoplastic agent for the treatment of breast, stomach, colon, and rectal cancers. It is more potent than 5-FU in these treatments, making it a valuable option for patients with these types of cancer.
Used in Tumor Treatment:
Doxifluridine is used as an antitumor agent, particularly effective in tumors, cell lines, or fibroblasts transformed by H-ras or trk oncogenes. It is a metabolite of the chemotherapeutic agent Capecitabine (C175650), which further enhances its role in cancer treatment.
Used in Antineoplastic Therapy:
As a pyrimidine antimetabolite, Doxifluridine is used in antineoplastic therapy to inhibit the growth and proliferation of cancer cells, making it a crucial component in the fight against various types of cancer.

Originator

Hoffmann-LaRoche (USA)

Biochem/physiol Actions

Doxifluridine is an antitumor agent efficient in tumors, cell lines or in fibroblasts transformed by H-ras or trk oncogenes. Possesses anticachectic activity which is independent of its antiproliferative activity.

InChI:InChI=1/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6?,8?/m1/s1

Upstream product

• 77180-87-1 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine 
• 13039-71-9 5-deoxy-1-methoxy-D-ribofuranoside 
• 78341-96-5 (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 66335-39-5 5′-deoxy-2′,3′-O-isopropylidene-5-fluorouridine 
• 532-20-7 D-Ribose 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 37105-93-4 1,2-O-isopropylidene-5-deoxy-α-D-ribofuranose 
• 15958-99-3 5'-deoxyuridine 
• 78948-09-1 acetyl hypofluorite 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 124012-42-6 5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine 
• 78341-98-7 Methyl-(5-desoxy-2,3-di-O-acetyl-D-ribofuranosid) 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 

Downstream Products

• 66335-39-5 5′-deoxy-2′,3′-O-isopropylidene-5-fluorouridine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 77180-87-1 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine 
• 51-21-8 5-fluorouracil 

Relevant articles and documents

Uracil nucleoside derivative and method for preparing deoxyuridine drug by using same (by machine translation)

The invention discloses (I) deoxy - D D-furan ribose 5 - styryl 1 - [2 - (1 - benzoate) derivative represented by the formula] and a preparation method, of the derivative, wherein the structure of the general formula (I) is shown. And the preparation method (I) of, deoxy - D D-furan ribose 5 - styryl 1 - [2 - (1 - benzoate) derivatives as above reaction raw materials can be used as a glycosyl donor to activate] under the conditions of the catalytic amount of the Lewis acid trifluoromethanesulfonate and N - iodosuccinimide, and, reaction efficient, yield 98%. reaching, is avoided in the conventional reaction system using an equivalent or excess of a Lewis acid, benzoyldiimide as a glycosyl donor. (by machine translation)

A Doxifluridine synthetic method

The invention relates to a synthesis method of doxifluridine: will be 5 - Fluorouracil, hexamethyldisilazane and ammonium sulfate refluxing reaction, the resulting double-silicon ether 5 - Fluorouracil with 5 - deoxy - triacetyl ribose in added to the methylene chloride, into the tin tetrachloride, obtained reaction liquid; the reaction liquid is poured into the clean water for hydrolysis, then layered, organic layer by the alkaline concentration recovery dichloromethane, to obtain core intermediate 2 ', 3' - O - di-ethyl - 5 - fluoro uracil nucleoside; intermediate adding ammonia in methanol solution to carry out saponification reaction, after the reaction, concentrating and recovering methanol, to get the crude product, refined crystal to obtain Doxifluridine. The method of the invention using a cheap and easily obtained 5 - fluoro uracil and 5 - deoxy - triacetyl ribose as raw materials, through the silicon ether, condensation, hydrolysis and saponification four-step reaction synthesizes Doxifluridine, greatly simplifying the production process, shortens the reaction time, the reaction is more complete, high-purity product.

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

Rapid continuous synthesis of 5′-deoxyribonucleosides in flow via Br?nsted acid catalyzed glycosylation

A general, green, and efficient Br?nsted acid-catalyzed glycosylation serves as a key step in the one-flow, multistep syntheses of several important 5′-deoxyribonucleoside pharmaceuticals.

A versatile synthesis of 5'-fenctionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors

We describe a chemo-enzymatic synthesis of modified nucleosides through lipase-catalyzed hydrolysis of their peracetylated precursors. It was found from screening of a large number of substrates that these enzymesregioselectivities were affected by the sugar and the nucleobase structures. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monodeprotecled purine and pyrimidine nucleosides useful as intermediates for the synthesis of high-value nucleosides and mononucleotides. By this approach, the chemo-enzymatic preparation of doxifluridine (14) and uridine 5'-monophosphate (5'-UMP, 15) from peracetylated uridine 1 was carried out. Elimination of many of the processing stages associated with existing methods was achieved, and higher yields and products of increased purity were generated. Wiley-VCH Verlag GmbH & Co. KGaA.

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.

TRANSDERMAL DEVICE CONTAINING POLYVINYLPYRROLIDONE AS SOLUBILITY ENHANCER

A blend of at least three polymers, including a soluble polyvinylpyrrolidone, in combination with a drug provides a pressure-sensitive adhesive composition for a transdermal drug delivery system in which the drug is delivered from the pressure-sensitive adhesive composition and through dermis when the pressure-sensitive adhesive composition is in contact with human skin. Soluble polyvinylpyrrolidone increases the solubility of drug without negatively affecting the adhesivity of the composition or the rate of drug delivery from the pressure-sensitive adhesive composition

Process for the preparation of a deoxyuridine derivative

A process for the preparation of 5′-deoxy-5-fluorouridine, which comprises, the transformation of, 2′,3′-O-isopropylidene-5-fluorouridine in the corresponding 5′-O-sulfonyl derivative subsequent reaction with alkaline or earth-alkaline iodides and after hydrolysis of the isopropylidene group, reduction of the 5′-deoxy-5′-iodo-5 -fluorouridine thus obtained, is described.

5'-deoxy-cytidine derivatives

Novel 5'-deoxy-cytidine derivatives represented by the general formula (I) wherein R1 is a hydrogen atom or a group easily hydrolyzable under physiological conditions; R2 is a hydrogen atom, or -CO-OR4 group [wherein R4 is a saturated or unsaturated, straight or branched hydrocarbon group consisting of one to fifteen carbon atoms, or a group of the formula -(CH2)n-Y (in which Y is cyclohexyl or phenyl; n is an integer from 0 to 4)]; R3 is a hydrogen atom, bromo, iodo, cyano, a C1-4 alkyl group [which may be substituted with halogen atom(s)], a vinyl or ethynyl group [which may be substituted with halogen atom(s), C1-4 alkyl, cycloalkyl, aralkyl, or aromatic ring which may have one or more hetero atom(s)], or an aralkyl group which may be substituted for use in medical therapy, especially tumor therapy.

5'deoxycytidine derivatives

Compounds of the formula (I) STR1 wherein R1 is each independently hydrogen or a group easily hydrolyzable under physiological conditions; R2 is --(CH2)n -cycloalkyl wherein cycloalkyl contains 3 to 5 carbon atoms and n is an integer from 0 to 4, heteroaryl-(lower-alkyl), (lower-alkoxy)-(lower-alkyl), aryloxy-(lower-alkyl), aralkyloxy-(lower-alkyl), (lower-alkylthio)-(lower-alkyl), arylthio-(lower-alkyl), aralkylthio-(lower-alkyl), oxo-(lower-alkyl), acylamino-(lower-alkyl), cyclic amino-(lower-alkyl), (2-oxocyclic amino)-(lower-alkyl) wherein the alkylene chain is unsubstituted or substituted with one or two lower-alkyl group(s); and R3 is iodo, or a vinyl or ethynyl group which group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, C1-4 alkyl, cycloalkyl, aralkyl, carbocyclic aromatic ring and heteorcyclic aromatic ring. The compounds of formula I are useful in the treatment of malignant diseases and can also be administered together with 5-fluorouracil or derivatives thereof to enhance the antitumour activity of the latter.