ChemicalBook >> CAS DataBase List >>2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride

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

CAS No.
10212-25-6
Chemical Name:
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
Synonyms
Cyclo-C;nsc-145668;Cyclo-Cr·HCl;Anhydro-.HCl;Anhydro-Cr.HCl;NSC 145668 HCl;ANCITABINE HCL;CYCLOCYTIDINE HCL;Cyclocytidine HC1;2,2'-Anhydro-C.Hcl
CBNumber:
CB5292165
Molecular Formula:
C9H12ClN3O4
Molecular Weight:
261.66
MDL Number:
MFCD00012636
MOL File:
10212-25-6.mol
Last updated:2024-11-19 23:02:33

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride 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)
FDA UNII 3T6920M469
NCI Drug Dictionary ancitabine hydrochloride

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Safety Statements  24/25
WGK Germany  2
RTECS  LV2615000
HS Code  29213000

2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A8598 Ancitabine hydrochloride 10212-25-6 1g $108 2024-03-01 Buy
TCI Chemical C2207 2,2'-O-Cyclocytidine Hydrochloride >98.0%(HPLC)(N) 10212-25-6 1g $48 2024-03-01 Buy
TCI Chemical C2207 2,2'-O-Cyclocytidine Hydrochloride >98.0%(HPLC)(N) 10212-25-6 5g $139 2024-03-01 Buy
Alfa Aesar J63845 Cyclocytidine hydrochloride, 98+% 10212-25-6 1g $51.65 2024-03-01 Buy
Alfa Aesar J63845 Cyclocytidine hydrochloride, 98+% 10212-25-6 5g $180 2021-12-16 Buy
Product number Packaging Price Buy
A8598 1g $108 Buy
C2207 1g $48 Buy
C2207 5g $139 Buy
J63845 1g $51.65 Buy
J63845 5g $180 Buy

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

Chemical Properties

white fine crystalline powder

Originator

Cyclo-C,Kohjin,Japan,1975

Uses

Ancitabine Hydrochloride is an antineoplastic agent.

Uses

Anti-tumor 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

Global( 357)Suppliers
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Hebei Weibang Biotechnology Co., Ltd
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View Lastest Price from 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride pictures 2024-12-20 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
10212-25-6
US $0.00 / Kg 1Kg 98% 20Ton Xinxiang Aurora Biotechnology Co.,Ltd.
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride pictures 2024-12-17 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride
10212-25-6
US $100.00 / kg 1kg 99% 2000kg hebei hongtan Biotechnology Co., Ltd
2,2'-Anhydro- 1-beta-D- arabinofuranosylcytosine hydrochloride pictures 2024-12-17 2,2'-Anhydro- 1-beta-D- arabinofuranosylcytosine hydrochloride
10212-25-6
US $100.00 / kg 1kg 99.9% 1000 hebei hongtan Biotechnology Co., Ltd
1-beta-d-arabinofuranosyl-2,2’-anhydro-cytosinhydrochloride hydroxy-6-imino-,monohydrochloride,stereoisomer nsc-145668 o-2,2’-cyclocytidinemonohydrochloride 2,2'-ANHYDRO-(1-BETA-D-ARABINOFURANOSYL)CYTOSINE HYDROCHLORIDE 2,2'-ANHYDROCYTIDINE HYDROCHLORIDE ANCITABINE HYDROCHLORIDE Ancitabine hydrochloride,2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride, Cyclo-C, Cyclocytidine ()-Cyclocytidine hydrochloride,2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride, 2,2′-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride, Ancitabine, O2,2′-Cyclocytidine CYCLOCYTIDINE HCL(RG) 2,2'-Anhydro-1-beta- Anhydro-Cr.HCl Cyclocytidine hydrochloride / 2,2'-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride 2,2'-Anhydrocytidine HCl O2-2'-CYCLOCYTIDINE HYDROCHLORIDE 2,2'-Anhydro-C.Hcl 2,2'-Anhydro-(1-beta-D-arabinofuranosyl)cytosine Hydrochloride Ancitabine Hydrochloride Cyclocytidini HydrochloriduM OCTD hydrochloride Hydrochloric cyclocylidine 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, hydrochloride (1:1), (2R,3R,3aS,9aR)- NSC 145668 HCl 2,2’-anhydro-1-beta-d-arabinofuranosylcytosinhydrochloride 2,2’-anhydroarabinosylcytosinehydrochloride 2,2’-anhydrocytarabinehydrochloride 2,2’-cyclocytidinehydrochloride 2,2’-o-cyclocytidinehydrochloride 3’:4,5)oxazolo(3,2-a)-pyrimidine-2-methanol,2,3,3a,9a-tetrahydro-3-6h-furo(2 cyclo-cmphydrochloride CYCLOCYTIDINE HCL (-)-CYCLOCYTIDINE HYDROCHLORIDE CYCLOCYTIDINE HYDROCHLORIDE 2,2-Anhydro-(1-B-D-Arabinofuranosyl)Cytosine Hydrochloride 2-2-ANHYDRO-1-B-D-ARABINOFURANOSYL*CYTOSINE HCL ANCITABINE HCL CYCLOCYTIDINE HCL(P) CyclocytidiniHydrochlorinum 2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride Ancitabine hydrochloride, O2,2μ-Cyclocytidine Cyclo-C, Cyclocytidine, 2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride Ancitabine, O2,2μ-Cyclocytidine, 2,2μ-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride, 2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride (-)-Cyclocytidine hydrochloride,99% Cyclo-C cyclocytidine hydrochlorine (2R,3R,3aS,9aR)-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo(2',3'4,5)oxazolo(3,2-a)pyrimidine-2-methanol {6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidine-2-methanol,} 2,3, 3a,9a-tetrahydro-3-hydroxy-6-imino-, {[2R-(2.alpha.,3.beta.,3a.beta.,9a.beta.)]-} 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine 6H-Furo(2',3':4,5)oxazolo(3,2-a)-pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy- 6-imino-, monohydrochloride, stereoisomer 2,2'-Anhydroaracytidine hydrochloride Ancitabine (Cyclocytidine) HCl Cyclocytidine HC1 Cytarabine Impurity 21 Ancitabine (Cyclocytidine) hydrochloride Cytidine reference substance Cyclo-Cr·HCl 2,2'-O-Cyclocytidine Hydrochloride > 2,2’-Cyclocytidine hydrochloride, Ancytabine 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride USP/EP/BP