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Amino Acid Modified Vitamin D 2 Derivatives, Synthesis and Applications

A technology of vitamins and amino acids, applied in the field of medicinal chemistry, can solve problems that have not been reported before, and achieve the effects of good inhibition, high yield, and simple operation

Inactive Publication Date: 2017-04-19
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 studies on the synthesis of vitamin D derivatives are mainly based on 1α,25(OH) 2 D. 3 For the modification of the side chain of the basic skeleton, and for the direct use of vitamin D 2 Very little work has been done to synthesize amino acid-modified derivatives as starting materials and study their anticancer activity, and the substitution of amino acids for vitamin D 2 The drug synthesis of the A ring has not been reported so far

Method used

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  • Amino Acid Modified Vitamin D <sub>2</sub> Derivatives, Synthesis and Applications
  • Amino Acid Modified Vitamin D <sub>2</sub> Derivatives, Synthesis and Applications
  • Amino Acid Modified Vitamin D <sub>2</sub> Derivatives, Synthesis and Applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Vitamin D combined with formula I structure 2 The synthetic route of the derivative, the synthesis of compound 1:

[0043] Add vitamin D to a 100mL three-neck flask 2(5.0g, 12.6mmol) and 50mL of ethanol were placed in a low-temperature circulation tank, slowly cooled to below -20°C, and then potassium permanganate (8.0g, 50.4mmol) 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. The reaction was then monitored by TLC (V ethyl acetate:V petroleum ether=1:1). After the reaction, it was cooled to room...

Embodiment 2

[0045] Vitamin D combined with formula I structure 2 The synthetic route of the derivative, the synthesis of compound 2:

[0046] Add compound 1 (2.02g, 4.69mmol), lead tetraacetate (8.07g, 18.2mmol) and 10mL toluene into a 50mL 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

[0048] Vitamin D combined with formula I structure 2 The synthetic route of the derivative, the synthesis of compound 3:

[0049] Concentrate and dry the crude product obtained in the previous step, weigh it (1.63 g, 5.90 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 (0.47 g, 12.44 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 org...

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Abstract

The invention discloses an amino acid modification based vitamin D2 derivative, synthesis and applications. Vitamin D2 fragment alcohol is prepared with the vitamin D2 serving as raw materials through redox reaction, and the amino acid modification based vitamin D2 derivative is synthesized with the vitamin D2 and the vitamin D2 fragment alcohol serving as the raw materials. The vitamin D2 derivative, the synthesis and the applications have the advantages that synthesis raw materials are easy to obtain, the reaction condition is mild, the operation can be performed simply, the yield is high, the newly synthesized vitamin D2 derivative has good inhibiting capacity towards human breast cancer cells MCF-7, and potential medicinal values are provided.

Description

technical field [0001] The present invention mainly relates to a vitamin D based on amino acid modification 2 Derivatives, synthesis and application belong to the field of medicinal chemistry. Background technique [0002] Vitamin D 2 As an important active substance of vitamin D, it is transported to the liver through the blood in the human body and is metabolized into 25-hydroxyvitamin D by 25-hydroxylase 3 , and then obtain 1α,25-dihydroxyvitamin D through hydroxylation at the 1α-position in the kidney 3 , can regulate calcium and phosphorus metabolism, inhibit cancer cell proliferation, regulate blood pressure and immune system, etc. Ergosterol undergoes a ring-opening reaction under the action of ultraviolet light and can be converted into vitamin D 2 . As follows, the three-dimensional structure of steroids in compound a and compound b and vitamin D 2 have a high degree of similarity, similarly, the vitamin D of compound c 3 Structure and Vitamin D 2 The fragme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C401/00C07C229/36C07C227/20A61P35/00
Inventor 方志杰戴焕然
Owner NANJING UNIV OF SCI & TECH