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Vitamin D2 glucoside analogue, synthesis and application thereof

A technology of vitamins and analogs, applied in the field of medicinal chemistry, to achieve good inhibitory effect, mild reaction conditions, and simple operation

Inactive Publication Date: 2015-06-17
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a large number of researches on the synthesis of vitamin D analogs are mainly based on 1,25-(OH) 2 D is the modification of the side chain of the basic skeleton, or it is obtained by breaking bonds at the 7,8-positions of vitamin D as a raw material (C, D rings and side chains) and then recombining with analogs of the A ring. 1,25-(OH) 2 Structural analogues of D, and for direct vitamin D 2 Little work has been done to synthesize glycoside analogues as starting materials and study their anticancer activity

Method used

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  • Vitamin D2 glucoside analogue, synthesis and application thereof
  • Vitamin D2 glucoside analogue, synthesis and application thereof
  • Vitamin D2 glucoside analogue, synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] In conjunction with the synthetic route of formula (I), the synthesis of compound 1:

[0039] Add vitamin D to a 100mL three-neck flask 2 (0.50g, 1.26mmol) and 50mL of ethanol were placed in a low-temperature circulation tank, and the temperature was slowly lowered to below -20°C, then potassium permanganate (0.80g, 5.04mmol) was dissolved in 20mL of water, and added dropwise to the reaction system Medium (control the temperature not to exceed -20°C). After the dropwise addition, keep the temperature between -30°C and -20°C, and continue to stir and react for 2.5h. Then the temperature was raised slowly, and the temperature was controlled between -17°C--15°C to continue the reaction for 1.5h. After that, the temperature was naturally raised to room temperature, and then slowly heated to 45° C., and the reaction was continued for 10 minutes. Then TLC monitored the reaction (V ethyl acetate: V petroleum ether = 1:1). After the reaction, it was cooled to room temperatu...

Embodiment 2

[0041] In conjunction with the synthetic route of formula (I), the synthesis of compound 2:

[0042] Compound 1 (0.10 g, 0.23 mmol), lead tetraacetate (0.13 g, 0.279 mmol) and 10 mL of toluene were added to a 50 mL two-necked flask respectively. Then nitrogen protection was introduced, and the stirring reaction was continued for 5 h at room temperature. The reaction was monitored by TLC (V ethyl acetate: V petroleum ether = 1:4). After the reaction is complete, filter and concentrate under reduced pressure to obtain the crude compound. This step does not require purification, and proceeds directly to the next step.

Embodiment 3

[0044] In conjunction with the synthetic route of formula (I), the synthesis of compound 3:

[0045] Concentrate and dry the crude product obtained in the previous step, weigh it (0.19 g, 0.68 mmol), dissolve it in 10 mL of redestilled toluene, and add 5 mL of ethanol. The reaction was placed in a low-temperature circulation tank, and the temperature was slowly lowered to -10°C. Sodium borohydride (0.10 g, 1.45 mmol) was then added slowly with stirring. After the addition, continue to stir the reaction at low temperature for 15 minutes, then place the reaction at room temperature, and continue to stir the reaction for 2 hours. The progress of the reaction was monitored by TLC (V ethyl acetate: V petroleum ether = 1:10). After the reaction was complete, an appropriate amount of water was slowly added at low temperature to quench the reaction. Then, 100 mL of ethyl acetate and 100 mL of water were added, and after shaking and separating, the organic layer was separated. The ...

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Abstract

The invention discloses a vitamin D2 glucoside analogue, a synthesis and an application thereof. According to the invention, vitamin D2 is taken as a raw material, vitamin D2 fragment alcohol is prepared through an oxidation reduction reaction, and then vitamin D2 and its fragment alcohol are respectively taken as raw materials for synthesizing structural analogues of a and b. The synthesis method has the advantage of easily available raw materials, mild reaction condition, simple operation, and high yield, the novel synthesized vitamin D2 glucoside analogue has good inhibition capability to human liver cancer cell Hep G2 and human breast cancer cell MCF-7, and has latent medicinal value.

Description

technical field [0001] The present invention mainly relates to vitamin D 2 The glycoside analogue, its synthesis and its application belong to the field of medicinal chemistry. Background technique [0002] As a natural natural resource, mushrooms are widely present in our life, and they have been paid attention to for a long time because of their good medicinal value. Many bioactive molecules with anticancer activity are isolated from different species of mushrooms. For example, compound a and compound b are two natural glycoside compounds extracted from plants respectively. Recently, it has been reported that compound a and compound b can inhibit the production of NO by lipopolysaccharide-stimulated macrophages and achieve the removal of peroxynitrite anion (ONOO - ) and has potential applications in the treatment of many diseases such as joint arthritis, atherosclerosis and cancer. [0003] Vitamin D 2 As an important active substance of vitamin D, its metabolite 1,2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H15/207C07H1/00A61P35/00
CPCC07B2200/07C07H1/00C07H15/207
Inventor 方志杰刘娅楠
Owner NANJING UNIV OF SCI & TECH
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