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

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

InChIKey

KZOWNALBTMILAP-JBMRGDGGSA-N

LogP

-2.301 (est)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

LV2615000

HS Code 

29213000

MSDS

• Language:English Provider:2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Usage And Synthesis

Chemical Properties

white fine crystalline powder

Originator

Cyclo-C,Kohjin,Japan,1975

Uses

Anti-tumor agent

Uses

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

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride(10212-25-6)Related Product Information

• β-nicotinamide mononucleotide, reduced form, disodium salt(NMNH)
• Yohimbine hydrochloride
• Nicotinamide riboside chloride
• NAD+
• β-Nicotinamide Mononucleotide
• (S)-3-Amino-1,2-propanediol
• O-Methylisourea hydrochloride
• Acetamidine hydrochloride
• o-methylisourea
• (S)-(+)-1-DIMETHYLAMINO-2-PROPANOL
• 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
• O-Ethylisourea hydrochloride
• Cytidine
• ETHYL FORMIMIDATE HYDROCHLORIDE
• Ancitabine
• Allylamine hydrochloride
• (R)-3-(Dimethylamino)-1,2-propanediol
• 3-AMINO-1-PROPANOL HYDROCHLORIDE