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α-Decitabine, also known as 2-Deoxy-D-α-ribopyranosyl-5-azacytosine, is a nucleoside analog and a potent inhibitor of DNA methylation. It is an isomer of 2-Deoxy-D-β-ribopyranosyl-5-azacytosine (D253525), which is an impurity of Decitabine and potentially carcinogenic. α-Decitabine plays a crucial role in the treatment of various cancers by targeting the epigenetic regulation of gene expression.

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  • 1,3,5-Triazin-2(1H)-one,4-amino-1-(2-deoxy-a-D-erythro-pentofuranosyl)-

    Cas No: 22432-95-7

  • USD $ 1.9-2.9 / Gram

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  • 22432-95-7 Structure
  • Basic information

    1. Product Name: α-Decitabine
    2. Synonyms: s-Triazin-2(1H)-one,4-amino-1-(2-deoxy-a-D-erythro-pentofuranosyl)- (8CI); 1-(2-Deoxy-a-D-ribofuranosyl)-5-azacytosine; NSC 127717; a-Decitabine
    3. CAS NO:22432-95-7
    4. Molecular Formula: C8H12N4O4
    5. Molecular Weight: 228.20528
    6. EINECS: N/A
    7. Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
    8. Mol File: 22432-95-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 485.8°Cat760mmHg
    3. Flash Point: 247.6°C
    4. Appearance: /
    5. Density: 1.9g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: -20°C Freezer
    8. Solubility: Methanol (Slightly, Heated), Water
    9. PKA: 14.02±0.60(Predicted)
    10. CAS DataBase Reference: α-Decitabine(CAS DataBase Reference)
    11. NIST Chemistry Reference: α-Decitabine(22432-95-7)
    12. EPA Substance Registry System: α-Decitabine(22432-95-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22432-95-7(Hazardous Substances Data)

22432-95-7 Usage

Uses

Used in Anticancer Applications:
α-Decitabine is used as an anticancer agent for its ability to inhibit DNA methylation, which results in the reactivation of silenced tumor suppressor genes and the induction of apoptosis in cancer cells. This makes it a valuable therapeutic option for the treatment of various types of cancer, including myelodysplastic syndromes (MDS), acute myeloid leukemia (AML), and other solid tumors.
Used in Epigenetic Therapy:
α-Decitabine is used as an epigenetic therapy agent to modulate gene expression and reverse the abnormal methylation patterns observed in cancer cells. By targeting DNA methyltransferase enzymes, it can restore normal cellular function and potentially prevent the development and progression of cancer.
Used in Drug Development:
α-Decitabine serves as a key compound in the development of new drugs and therapies targeting epigenetic mechanisms in cancer. Its unique properties and mechanism of action make it an attractive candidate for combination therapies and the development of novel agents with improved efficacy and reduced toxicity.

Check Digit Verification of cas no

The CAS Registry Mumber 22432-95-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,4,3 and 2 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 22432-95:
(7*2)+(6*2)+(5*4)+(4*3)+(3*2)+(2*9)+(1*5)=87
87 % 10 = 7
So 22432-95-7 is a valid CAS Registry Number.

22432-95-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-amino-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one

1.2 Other means of identification

Product number -
Other names EINECS 219-089-4

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22432-95-7 SDS

22432-95-7Relevant articles and documents

Development of an immobilized biocatalyst based on Bacillus psychrosaccharolyticus NDT for the preparative synthesis of trifluridine and decytabine

Fresco-Taboada, Alba,Serra, Immacolata,Arroyo, Miguel,Fernández-Lucas, Jesús,De La Mata, Isabel,Terreni, Marco

, p. 197 - 204 (2016)

The immobilization of Bacillus psychrosaccharolyticus nucleoside 2′-deoxyribosyltransferase was deeply investigated and finally optimized. The best immobilization procedure resulted to be ionic adsorption on PEI 600 Da agarose followed by crosslinking with 70% oxidized dextran (20 kDa). The percentage of recovered activity was further improved (from 21% to 33%) by the addition of 20% glycerol to the immobilization mixture. The resulting biocatalyst showed a stability profile similar to that of the soluble enzyme and it was used for the preparative synthesis of trifluridine and decytabine obtaining conversions ranging from 50% to 76%.

Decitabine intermediate compound VI

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Paragraph 0055; 0124-0132, (2021/01/24)

The invention belongs to the technical field of chemical synthesis, and provides a decitabine intermediate compound. A preparation route of the decitabine intermediate compound comprises the followingsteps: taking an oxymethyl compound of a hydroxyl group at a 1 site of 2-deoxy-D-ribose as a raw material, protecting a hydroxyl group at a 3 site and a hydroxyl group at a 5 site respectively, then performing acetylation substitution on a 1 site of sugar, and further treating to obtain the compound. The method is simple and convenient to operate, does not need special equipment, is good in product purity and high in yield, and is suitable for industrial production; decitabine is further synthesized by utilizing the compound, so that the stereoselectivity is high, and the purity isgood.

Decitabine intermediate compound V

-

, (2021/01/24)

The invention belongs to the technical field of chemical synthesis, and provides a decitabine intermediate compound. A preparation route of the decitabine intermediate compound comprises the followingsteps: taking an oxymethyl compound of 2-deoxy-D-ribose 1 site hydroxyl as a raw material, respectively protecting 3 site and 5 site hydroxyl, and further treating to obtain the compound provided by the invention. The method is simple and convenient to operate, does not need special equipment, and is good in product purity, high in yield and suitable for industrial production; and decitabine is further synthesized by utilizing the compound, so that the compound is high in stereoselectivity and good in purity.

Preparation method of decitabine

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Paragraph 0010; 0035-0036; 0038-0039; 0041-0042; 0044-0045, (2021/01/15)

The invention belongs to the technical field of organic synthesis, and provides a preparation method of decitabine. The preparation method specifically comprises the following steps: first carrying out reflux extraction to obtain a mixture of decitabine alpha and beta isomers, and then separating the isomers by applying the supercritical fluid technology to obtain high-purity decitabine. Comparedwith the prior art, the technical method which is simple in operation process, high in separation efficiency, high in product yield, high in final product purity and suitable for industrial productionis provided.

2-deoxy-D-ribose derivative

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Paragraph 0086-0090, (2020/08/09)

The invention belongs to the field of medicine synthesis, and provides a 2-deoxy-D-ribose derivative (III). When the derivative (III) is used for preparing decitabine, the stereoselectivity is good, and the yield is high. The invention provides a preparation method of the derivative. The preparation method comprises the following steps: step a, carrying out oxygen methylation on 1-position hydroxyl of 2-deoxy-D-ribose; and step b, protecting hydroxyl groups at positions 3 and 5, and further carrying out sulfonation on 1-position oxymethyl. The method is simple and convenient to operate, free of special equipment, good in product purity, high in yield and suitable for industrial production.

Synthetic method of decitabine

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Paragraph 0052; 0053, (2019/08/01)

The present invention relates to a synthetic method of decitabine, and discloses a method for synthesizing a compound as shown in a formula I, The method comprises the steps of: reacting a compound IIwith a compound III by a following reaction in a solvent under the action of TMSOTf to obtain a compound I. The synthetic method of the invention has the advantages that the raw materials are easy toobtain, the operation is safe, the conditions are mild and easy to control, and a solid product obtained by an acylation protection is easy to be crystallized and purified, which is favorable for thenext reaction and improves the selectivity of a final beta-isomer product, no further conversion to hydroxymethyl is required, the reaction step is simplified, the reaction yield of each step is good, the atomic economy is high, and the method is suitable for a large number of industrial production and the like.

Preparation method of beta-nucleoside compound

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Paragraph 0108; 0112; 0113; 0114; 0115; 0120; 0127; 0136, (2018/07/30)

The invention provides a method for preparing beta-nucleoside or analogue thereof, comprising the following steps: 1) enabling nitrogenous base or analogue thereof to generate silylanizing reaction under the existence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), to obtain the nitrogenous base or analogue thereof protected by trimethylsilyl; 2) enabling a reaction liquid to directly perform glycosylation reaction with quintuple cyclose or hexahydric cyclose sealed by a hydroxy protection group, so as to obtain a sealed beta-nucleoside or analogue thereof; 3) performing protection groupremoval reaction, to obtain the beta-nucleoside or analogue thereof. The method disclosed by the invention is simple in operation, energy-saving and environment-friendly, a key intermediate of the beta-nucleoside or analogue thereof is prepared by a one-pot methoid, and the yield of beta configuration substance is remarkably increased, and the preparation method is suitable for industrial application.

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

Stepchenko, Vladimir A.,Miroshnikov, Anatoly I.,Seela, Frank,Mikhailopulo, Igor A.

, p. 2588 - 2601 (2017/01/09)

The trans-2-deoxyribosylation of 4-thiouracil (4SUra) and 2-thiouracil (2SUra), as well as 6-azauracil, 6-azathymine and 6-aza-2-thiothymine was studied using dG and E. coli purine nucleoside phosphorylase (PNP) for the in situ generation of 2-deoxy-α-D-ribofuranose-1-phosphate (dRib-1P) followed by its coupling with the bases catalyzed by either E. coli thymidine (TP) or uridine (UP) phosphorylases. 4SUra revealed satisfactory substrate activity for UP and, unexpectedly, complete inertness for TP; no formation of 2′-deoxy-2-thiouridine (2SUd) was observed under analogous reaction conditions in the presence of UP and TP. On the contrary, 2SU, 2SUd, 4STd and 2STd are good substrates for both UP and TP; moreover, 2SU, 4STd and 2′-deoxy-5-azacytidine (Decitabine) are substrates for PNP and the phosphorolysis of the latter is reversible. Condensation of 2SUra and 5-azacytosine with dRib-1P (Ba salt) catalyzed by the accordant UP and PNP in Tris·HCl buffer gave 2SUd and 2′-deoxy-5-azacytidine in 27% and 15% yields, respectively. 6-Azauracil and 6-azathymine showed good substrate properties for both TP and UP, whereas only TP recognizes 2-thio-6-azathymine as a substrate. 5-Phenyl and 5-tert-butyl derivatives of 6-azauracil and its 2-thioxo derivative were tested as substrates for UP and TP, and only 5-phenyl- and 5-tert-butyl-6-azauracils displayed very low substrate activity. The role of structural peculiarities and electronic properties in the substrate recognition by E. coli nucleoside phosphorylases is discussed.

Synthesis method of decitabine for treating primary or secondary leukemia

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Paragraph 0026; 0027; 0028; 0029, (2017/01/09)

The invention discloses a synthesis method of decitabine for treating primary or secondary leukemia. The method comprises the following steps: 1) adding 1-chloro-2-deoxy-D-ribofuranose, cobalt nitrate and (R)-1,1'-linked-2-naphthol in DMF, stirring and mixing for 1-2 hours at 45-60 DEG C, then cooling to room temperature, and filtering to obtain mixture M containing 1-chloro-2-deoxy-D-ribofuranose complex; and 2) in the presence of triethylamine, adding 2,4-bis-trimethylsilyl-S-triazine in the mixture M obtained in the step 1), stirring for reacting for 6-8 hours at 30-40 DEG C, soaking in water, extracting with dichloromethane, washing with dilute hydrochloric acid, washing with saturated sodium bicarbonate, concentrating, and carrying out ethanol recrystallization to obtain decitabine. The method for preparing decitabine effectively improves the selectivity of a beta product and the yield of decitabine, thereby providing a new way for preparing decitabine.

An anti-cancer drug to the preparation method of Decitabine (by machine translation)

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Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032-0061, (2017/01/26)

The invention discloses anti-cancer drugs in Decitabine preparation method, the method comprises: 1) the 1 - chloro - 2 - deoxy - D - ribofuranosyl, two palladium chloride, (S)- (-) - 1, 1 '- binaphthyl - 2, 2' - double-b (3, 5 - xylyl) phosphine is added to in DMF, 45 - 60 °C stirring and mixing 1 - 2 hours, then cooling to room temperature, filter, containing the 1 - chloro - 2 - deoxy - D - ribofuranosyl complex mixture M; 2) in the presence of triethylamine, to 2, 4 - bistrimethylsilyl - S - triazine adding step 1) the resulting mixture in the M 30 - 40 °C stirring for 6 - 8 hours, tilting in a water, dichloromethane extraction, dilute hydrochloric acid washing, saturated sodium bicarbonate washing, concentrating, ethanol recrystallize to get in Decitabine. The preparation of this invention in Decitabine of β method effectively improves the product selectivity and the yield of Decitabine, for preparation in Decitabine provides new means. (by machine translation)

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