| Identification | Back Directory | [Name]
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride | [CAS]
10212-25-6 | [Synonyms]
Cyclo-C
nsc-145668
ANCITABINE HCL
Anhydro-Cr.HCl
NSC 145668 HCl
CYCLOCYTIDINE HCL
OCTD hydrochloride
2,2'-Anhydro-C.Hcl
2,2'-Anhydro-1-beta-
CYCLOCYTIDINE HCL(P)
CYCLOCYTIDINE HCL(RG)
cyclo-cmphydrochloride
ANCITABINE HYDROCHLORIDE
2,2'-Anhydrocytidine HCl
Hydrochloric cyclocylidine
CyclocytidiniHydrochlorinum
cyclocytidine hydrochlorine
CYCLOCYTIDINE HYDROCHLORIDE
Cyclocytidini HydrochloriduM
(-)-CYCLOCYTIDINE HYDROCHLORIDE
2,2’-cyclocytidinehydrochloride
(-)-Cyclocytidine hydrochloride
2,2’-o-cyclocytidinehydrochloride
O2-2'-CYCLOCYTIDINE HYDROCHLORIDE
2,2'-ANHYDROCYTIDINE HYDROCHLORIDE
2,2’-anhydrocytarabinehydrochloride
(-)-Cyclocytidine hydrochloride,99%
2,2'-Anhydroaracytidine hydrochloride
o-2,2’-cyclocytidinemonohydrochloride
2,2’-anhydroarabinosylcytosinehydrochloride
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine
2-2-ANHYDRO-1-B-D-ARABINOFURANOSYL*CYTOSINE HCL
Ancitabine hydrochloride, O2,2μ-Cyclocytidine
hydroxy-6-imino-,monohydrochloride,stereoisomer
2,2’-anhydro-1-beta-d-arabinofuranosylcytosinhydrochloride
2,2-Anhydro-(1-B-D-Arabinofuranosyl)Cytosine Hydrochloride
1-beta-d-arabinofuranosyl-2,2’-anhydro-cytosinhydrochloride
2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride
2,2'-ANHYDRO-(1-BETA-D-ARABINOFURANOSYL)CYTOSINE HYDROCHLORIDE
3’:4,5)oxazolo(3,2-a)-pyrimidine-2-methanol,2,3,3a,9a-tetrahydro-3-6h-furo(2
Cyclo-C, Cyclocytidine, 2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride
2,2'-Anhydro-(1-beta-D-arabinofuranosyl)cytosine Hydrochloride
Ancitabine Hydrochloride
Cyclocytidine hydrochloride/2,2'-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride
(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
Ancitabine hydrochloride,2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride, Cyclo-C, Cyclocytidine
6H-Furo(2',3':4,5)oxazolo(3,2-a)-pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, monohydrochloride, stereoisomer
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)-
{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.)]-}
Ancitabine, O2,2μ-Cyclocytidine, 2,2μ-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride, 2,2μ-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride
()-Cyclocytidine hydrochloride,2,2′-Anhydro-(1-β-D-arabinofuranosyl)cytosine hydrochloride, 2,2′-Anhydro-1-β-D-arabinofuranosylcytosine hydrochloride, Ancitabine, O2,2′-Cyclocytidine | [EINECS(EC#)]
233-515-6 | [Molecular Formula]
C9H12ClN3O4 | [MDL Number]
MFCD00012636 | [MOL File]
10212-25-6.mol | [Molecular Weight]
261.66 |
| Chemical Properties | Back Directory | [Appearance]
white fine crystalline powder | [Melting point ]
269-270 °C (dec.)(lit.) | [alpha ]
-21.8 º (c=2,water) | [refractive index ]
-21 ° (C=2, H2O) | [storage temp. ]
−20°C
| [solubility ]
Methanol (Slightly), Water (Sparingly) | [form ]
Powder | [color ]
White | [Merck ]
629 | [InChIKey]
KZOWNALBTMILAP-JBMRGDGGSA-N | [LogP]
-2.301 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
white fine crystalline powder | [Usage]
antineoplastic | [Originator]
Cyclo-C,Kohjin,Japan,1975 | [Uses]
Ancitabine Hydrochloride is an antineoplastic agent. | [Uses]
antineoplastic | [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 |
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