Introduction：Basic information about 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride CAS 10212-25-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Basic information
| Product Name: | 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride |
| Synonyms: | 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 |
| CAS: | 10212-25-6 |
| MF: | C9H12ClN3O4 |
| MW: | 261.66 |
| EINECS: | 233-515-6 |
| Product Categories: | API intermediates;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;10212-25-6 |
| Mol File: | 10212-25-6.mol |
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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 |
| InChI | InChI=1/C9H11N3O4.ClH/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8;/h1-2,4,6-8,10,13-14H,3H2;1H/t4-,6-,7+,8-;/s3 |
| InChIKey | KZOWNALBTMILAP-JBMRGDGGSA-N |
| SMILES | [C@@H]12O[C@H](CO)[C@@H](O)[C@@H]1OC1=NC(=N)C=CN21.Cl |&1:0,2,5,7,r| |
| LogP | -2.301 (est) |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | 2 |
| RTECS | LV2615000 |
| HS Code | 29213000 |
| Storage Class | 11 - Combustible Solids |
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 reactedwith trityl chloride to give 5'-o-trityluridine; (2) Imidazole is reacted withthiophosgene 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 uracilproduct is converted to the thiouracil using hydrogen sulfide; (4) The tritylgroup is removed by treatment with 80% acetic acid; (5) A triacetylatedproduct is obtained using acetic anhydride; (6) A dithiouracil is prepared fromthe uracil intermediate using phosphate pentasulfide.
Preparation of 1-(β-D-arabinofuranosyl)-2-thiocytosine: A solution of 2.0 g of1-(2',3',5'-O-triacetyl-β-D-arabinofuranosyl)-2,4-dithiouracilin 100 ml ofmethanol is saturated with anhydrous ammonia at 0°C. The mixture, in aglass liner, is heated in a pressure bomb at 100°C for three hours. Thereaction mixture is concentrated to a gum in vacuum, and most of thebyproduct acetamide is removed by sublimation at 60°C/0.1 mm. The residueis chromatographed on 100 g of silica gel. Elution of the column withmethylene chloride-methanol mixtures with methanol concentrations of 2-25%gives fractions containing acetamide and a series of brown gums. The desiredproduct is eluted with 30% methanol-methylene chloride to give a total yieldof 0.386 g (30%), MP 175-180°C (dec.). Recrystallization from methanolisopropanolfurnishes an analytical sample, MP 180-182°C (dec.).
To a solution of 80 mg of 1-(β-D-arabinofuranosyl)-2-thiocytosine in 12 ml ofwater is added dropwise 3 ml of a 1 M bromine solution in carbontetrachloride. At this point the color of the bromine persists for about 2-3minutes after each addition. The unreacted bromine is blown off with a streamof nitrogen, and the reaction mixture is concentrated to a syrup in vacuumusing a bath temperature less than 50°C. The residue is evaporated threetimes with 10 ml portions of ethanol, whereupon it crystallizes. The product istriturated 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 ammoniayields the base which may then be converted to the hydrochloride. |
| Therapeutic Function | Antineoplastic |
| Biological Activity | Antineoplastic |
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride Preparation Products And Raw materials
| Raw materials | Ethanol-->Calcium gluconate-->Cyanamide-->Cation exchange resin,strong acidic styrene-->Propyne-->Anion exchange resin,strong basic quarternary ammoniumⅠ-->Oxazoline-->FERROUS GLUCONATE BP/USP-->Ammonia-->1-beta-D-Arabinofuranosyluracil-->Triphenylmethyl Chloride-->Acetic acid-->Hydrochloric acid-->Thiophosgene-->Imidazole-->Phosphorus pentasulfide-->Acetic anhydride-->Hydrogen Sulfide |
