2-deoxy-d-ribose derivates, preparation method and use thereof

A technology for derivatives and uses, applied in the field of derivatives of 2-deoxy-D-ribose and their preparation, can solve the problems of danger, incomplete reaction, hydrolysis and the like

Inactive Publication Date: 2008-11-26
SHANGHAI INST OF PHARMA IND CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, according to the literature, deprotection with methanol solution of saturated ammonia results in a very incomplete reaction. If heating and prolonging the reaction time, the degradation products will increase
The literature (J.Org.Chem., 1986, 51:3211-3213) mentions that using Tol as the hydroxyl protecting group of sugar will cause the hydrolysis of the product in the last step of deprotection, endangering the whole route

Method used

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  • 2-deoxy-d-ribose derivates, preparation method and use thereof
  • 2-deoxy-d-ribose derivates, preparation method and use thereof
  • 2-deoxy-d-ribose derivates, preparation method and use thereof

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preparation example Construction

[0089] The invention provides a preparation method of the compound of the general formula A, which comprises substituting and protecting the three hydroxyl groups at positions 1, 3 and 5 of 2-deoxy-D-ribose (formula II) through acetylation to obtain the compound of the general formula A.

[0090]

[0091] Formula II General Formula A

[0092] The compound of formula II is mixed with a suitable solvent containing a deacidifying agent, and the substituted acetylation reagent is slowly added dropwise at -50°C to 30°C (preferably -10°C to 10°C). °C-30°C) for 15-45 hours (preferably 20-30 hours), to obtain the compound of general formula A. Wherein the molar ratio of the substituted acetylating agent to the compound of formula II is 1-9:1 (preferably 3-6:1, more preferably 3-4:1).

[0093] The suitable solvent containing deacidification agent includes: tertiary amine (pyridine, lower alkane substituted pyridine, triethylamine, etc.), or a mixed system of various aprotic polar s...

Embodiment 1

[0120] 1,3,5-tris(methoxyacetyl)-2-deoxy-D-ribose (general formula A, R=CH 3 OCH 2 ) preparation

[0121] 2-Deoxy-D-ribose (II) (20g) was dissolved in pyridine (60ml), cooled to 0°C, methoxyacetic anhydride (75ml) was slowly added dropwise, and the mixture was stirred at room temperature for 30 hours. Add dichloromethane for dilution, adjust the pH value to neutral with saturated aqueous sodium bicarbonate solution, wash the organic phase successively with 2mol / L hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the Formula A compound (R=CH 3 OCH 2 ), as light yellow syrup (56g). Without purification, it was directly put into the next reaction. ESI-MS(m / z)373(M+Na) + .

Embodiment 2

[0123] 1,3,5-tris(chloroacetyl)-2-deoxy-D-ribose (general formula A, R=ClCH 2 ) preparation

[0124] 2-Deoxy-D-ribose (II) (20g) was dissolved in pyridine (60ml), cooled to -5°C, chloroacetyl chloride (38ml) was slowly added dropwise, and the mixture was stirred at room temperature for 24 hours. Add dichloromethane for dilution, adjust the pH value to neutral with saturated aqueous sodium bicarbonate solution, wash the organic phase successively with 2mol / L hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the Formula A compound (R=ClCH 2 ) is pale yellow syrup (54g). Without purification, it was directly put into the next reaction. ESI-MS(m / z)385(M+Na) + .

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Abstract

The invention discloses a derivant for 2-deoxy-D-ribose, which is a compound as shown in the constitutional formula A on the right; R is selected from CH3(CH2)n-, CH3(CH2)n-Y-CH2-, X-CH2-, CH3(CH2)nCH(X)-, X2-CH-, CH3(CH2)nC(X)2- or CX3-; wherein, Y is selected from oxygen or sulfur; X is selected from fluorine, chlorine, bromine or iodine; n is equal to 0-5. The invention also provides the preparation method and the application of the compound with the general formula A. The compound with the general formula A includes Alpha anomer, Beta anomer and the mixture thereof.

Description

technical field [0001] The present invention relates to a new compound, in particular to a derivative of 2-deoxy-D-ribose and its preparation method and use. Background technique [0002] It has been reported in the literature (J.Med.Chem., 1985, 28, 904-910) that 2-deoxy-D-ribose (formula II) 1, 3, and 5-position triacetylate (general formula A, R=CH 3 ), but other 2-deoxy-D-ribose (formula II) 1, 3, 5 three-substituted acetylate (general formula A, R≠CH 3 ) has not been reported. [0003] [0004] Decitabine (formula I, decitabine) is an antitumor drug, its chemical name is: 4-amino-1-(2-deoxy-β-D-erythro-pentofuranoside)-1,3, 5-Triazin-2(1H)-one, other names: 5-aza-2-deoxycytidine. Its indications include myelodysplastic syndrome (myelodysplasticsyndromes, MDS) and so on. Its structural formula is as follows: [0005] [0006] Formula I [0007] According to literature reports (Collect.Czech.Chem.Commun., 1964,29:2576-2577), the method for preparing decitabine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/02C07H17/02
Inventor 张庆文吴晓燕益兵
Owner SHANGHAI INST OF PHARMA IND CO LTD
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