1034301-08-0

Basic information

• Product Name: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine
• Synonyms: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine;4-Amino-1-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-beta-D-ribofuranosyl]-1,3,5-triazin-2(1H)-one;3',5'-Bis-O-(4-chlorobenzoyl)-2-deoxy-5-azacytosine;3',5'-Bis-O-(4-chlorobenzoyl)-2-deoxy-5-azacytosine 4-Amino-1-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-beta-D-ribofuranosyl]-1,3,5-triazin-2(1H)-one;(2R,3S,5R)-5-(4-Amino-2-oxo-1,3,5-triazin-1(2H)-yl)-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate
• CAS NO: 1034301-08-0
• Molecular Formula: C₂₂H₁₈Cl₂N₄O₆
• Molecular Weight: 505.31
• EINECS: 2017-001-1
• Mol File: 1034301-08-0.mol

Chemical Properties

• Boiling Point: 642.6 °C at 760 mmHg
• Flash Point: 342.4 °C
• Appearance: /
• Density: 1.58
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Very Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.38±0.20(Predicted)
• CAS DataBase Reference: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine(1034301-08-0)
• EPA Substance Registry System: 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine(1034301-08-0)

Safety Data

• Hazardous Substances Data: 1034301-08-0(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine is used as an anticancer agent for the treatment of pancreatic endocrine tumor cell lines. It works by inhibiting the growth of these cancer cells, making it a valuable tool in the fight against this specific type of cancer.
Used in Pharmaceutical Research:
In addition to its direct application in cancer treatment, 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine also holds promise in the field of pharmaceutical research. Its unique chemical properties and potential effects on cancer cells make it an interesting compound for further study and development, with the aim of discovering new treatments and therapies for various types of cancer.
Used in Drug Development:
The compound's ability to inhibit the growth of pancreatic endocrine tumor cell lines also makes it a valuable asset in the development of new drugs and therapies. Researchers can use 3',5'-di-o-p-chlorobenzoyl-2-deoxy-5-azacytosine as a starting point or reference compound when designing and testing new drugs, potentially leading to the creation of more effective and targeted cancer treatments.

Upstream product

• 21740-23-8 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride 
• 52523-35-0 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine 
• 3601-90-9 5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate 
• 533-67-5 2-Deoxy-D-ribose 

Downstream Products

• 2353-33-5 5-aza-2'-deoxycytidine 

Relevant articles and documents

Method for synthesizing decitabine intermediate

The invention relates to a method for synthesizing a decitabine intermediate, in particular to a method for synthesizing the decitabine intermediate with a structure shown in a formula 2. According tothe method, the purity of the intermediate can be greatly improved, so that the purification operation of decitabine is reduced, a transition state intermediate compound is successfully separated forthe first time, and the total yield of decitabine is increased by three times.

Synthetic method of decitabine

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

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.

SYNTHESIS OF NUCLEOSIDES

A process for the preparation of nucleosides, derivatives and analogues thereof by coupling reaction of a protected suitable nitrogeneous purine or pyrimidine base, a derivative or analogue thereof and a protected suitable sugar in the presence of SnCl4 comprising the removal of SnCl4 by adding DMSO directly into the reaction mixture is described. Preferably said process is used for the preparation of antiviral and antitumor agents having a nucleoside or nucleoside-like structure, still more preferably for the preparation of azacytidine, decitabine, chlorfarabine, cladribine, mizoribine. A residual tin content lower than 300 ppm is obtained with said process.

PROCESSES FOR PRODUCING DECITABINE

New processes for producing decitabine are provided.

Method of producing 2' -deoxy-5-azacytidine (Decitabine)

Summary Method of producing 2'-deoxy-5-azacytidine (Decitabine) by providing a compound of formula (I): wherein R is a removable substituent known per se; and R1 is a glycoside donor preferably a 1-halogen derivative, an imidate preferably the trichloromethyl derivative, or a thio-alkyl derivative; further providing a silylated base of formula (II): wherein R2 is a protecting group, preferably a trimethylsilyl TMS)-residue; reacting the compound of formula (I) and the compound of formula (II) together in a suitable anhydrous solvent and in the presence of a suitable catalyst; and removing the substituents R from the compound obtained in order to obtain the compound 2'-deoxy-5-azacytidine (Decitabine), characterized in that said catalyst is selected from the group comprising a salt of an aliphatic sulphonic acid and/or the salt of a optionally substituted aromatic sulphonic acid.