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HomeProduct name list2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

Synonym(s):2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride;Cyclo-C;Cyclocytidine

  • CAS NO.:10212-25-6
  • Empirical Formula: C9H12ClN3O4
  • Molecular Weight: 261.66
  • MDL number: MFCD00012636
  • EINECS: 233-515-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 13:31:19
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Structural

What is 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride?

Chemical properties

white fine crystalline powder

Originator

Cyclo-C,Kohjin,Japan,1975

The Uses of 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

antineoplastic

The Uses of 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

Anti-tumor agent

The Uses of 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

Ancitabine Hydrochloride is an antineoplastic agent.

What are the applications of Application

Ancitabine hydrochloride is an antineoplastic agent

Definition

ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of ancitabine and hydrogen chloride.

Manufacturing Process

A series of reaction steps may be employed in which: (1) Uridine is reacted with trityl chloride to give 5'-o-trityluridine; (2) Imidazole is reacted with thiophosgene and that product reacted with the 5'-o-trityluridine to give 2,2'- anhydro-1-(5'-o-trityl-β-D-arabinofuranosyl)uracil; (3) The preceding uracil product is converted to the thiouracil using hydrogen sulfide; (4) The trityl group is removed by treatment with 80% acetic acid; (5) A triacetylated product is obtained using acetic anhydride; (6) A dithiouracil is prepared from the uracil intermediate using phosphate pentasulfide.
Preparation of 1-(β-D-arabinofuranosyl)-2-thiocytosine: A solution of 2.0 g of 1-(2',3',5'-O-triacetyl-β-D-arabinofuranosyl)-2,4-dithiouracilin 100 ml of methanol is saturated with anhydrous ammonia at 0°C. The mixture, in a glass liner, is heated in a pressure bomb at 100°C for three hours. The reaction mixture is concentrated to a gum in vacuum, and most of the byproduct acetamide is removed by sublimation at 60°C/0.1 mm. The residue is chromatographed on 100 g of silica gel. Elution of the column with methylene chloride-methanol mixtures with methanol concentrations of 2-25% gives fractions containing acetamide and a series of brown gums. The desired product is eluted with 30% methanol-methylene chloride to give a total yield of 0.386 g (30%), MP 175-180°C (dec.). Recrystallization from methanolisopropanol furnishes an analytical sample, MP 180-182°C (dec.).
To a solution of 80 mg of 1-(β-D-arabinofuranosyl)-2-thiocytosine in 12 ml of water is added dropwise 3 ml of a 1 M bromine solution in carbon tetrachloride. At this point the color of the bromine persists for about 2-3 minutes after each addition. The unreacted bromine is blown off with a stream of nitrogen, and the reaction mixture is concentrated to a syrup in vacuum using a bath temperature less than 50°C. The residue is evaporated three times with 10 ml portions of ethanol, whereupon it crystallizes. The product is triturated with cold ethanol and with ether to obtain 17 mg of 2,2'-anhydro-1- (β-D-arabinofuranosyl)cytosine hydrobromide, MP 240°C (dec.).
Treatment of the hydrobromide with a slight excess of ethanolic ammonia yields the base which may then be converted to the hydrochloride.

Therapeutic Function

Antineoplastic

Properties of 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

Melting point: 269-270 °C (dec.)(lit.)
alpha  -21.8 º (c=2,water)
refractive index  -21 ° (C=2, H2O)
storage temp.  Inert atmosphere,2-8°C
solubility  Methanol (Slightly), Water (Sparingly)
form  Powder
color  White
Merck  14,629

Safety information for 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

InChIKey KZOWNALBTMILAP-JBMRGDGGSA-N

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