10212-25-6 Usage
Uses
Used in Pharmaceutical Industry:
2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride is used as an anti-tumor agent for its antineoplastic properties. It is particularly effective against various types of cancer, including solid tumors, due to its ability to inhibit the growth and progression of cancer cells.
As an antineoplastic agent, 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride is used for its potential to treat cancer by interfering with the DNA synthesis and function of cancer cells, leading to their death and preventing the spread of the disease.
Furthermore, 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine hydrochloride can be used in combination with other chemotherapeutic drugs to enhance the overall effectiveness of cancer treatment, making it a valuable component in the development of novel cancer therapies.
Originator
Cyclo-C,Kohjin,Japan,1975
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
Check Digit Verification of cas no
The CAS Registry Mumber 10212-25-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,2,1 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 10212-25:
(7*1)+(6*0)+(5*2)+(4*1)+(3*2)+(2*2)+(1*5)=36
36 % 10 = 6
So 10212-25-6 is a valid CAS Registry Number.
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-;/m1./s1
10212-25-6Relevant articles and documents
Preparation method of cytarabine hydrochloride
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Paragraph 0101-0103, (2019/03/28)
The invention provides a preparation method of cytarabine hydrochloride. The preparation method comprises following steps: A, cytidine and acetylsalicyl chloride are reacted so as to obtain acetyl cyclocytidine; B, acetyl cyclocytidine is subjected to deprotection in a hydrochloric acid methanol solution so as to obtain cyclocytidine hydrochloride; and C, cyclocytidine hydrochloride is subjected to ring-opening reaction so as to obtain cytarabine hydrochloride. The preparation method of cytarabine hydrochloride possesses following advantages: the raw materials are cheap and easily available; using of high toxicity substances difficult to remove is avoided; the preparation method is safe, and is friendly to the environment; and product yield and purity are high.
Process for producing 2,2'-o-cyclonucleosides nucleosides, and analogs thereof
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, (2008/06/13)
A novel process is provided for producing a nucleoside, such as cytarabine, or a nucleoside analogue, comprising the step of reacting 2,2'-O-cyclonucleoside or an analogue thereof with an amine. Preferably, the process is conducted in the presence of an aqueous solvent. A novel process for the production of the precursor 2,2'-O-cyclonucleoside compounds and pharmaceutically acceptable salts thereof is also provided which comprises reacting a 2,3'-O-diaikylstannylene nucleoside compound with an amine in the presence of a sulfonyl compound. Cytarabine is a known antineoplastic and antiviral agent.
