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Alpha-pinene derivative and preparation method and application thereof

A derivative, pinene technology, applied in the field of α-pinene derivatives and their preparation, can solve the problems of few reports and the like, and achieve the effect of good anti-liver cancer activity

Inactive Publication Date: 2016-04-13
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the introduction of organic acid structures into the structure of the natural product α-pinene to obtain α-pinene derivatives with higher activity is less reported.

Method used

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  • Alpha-pinene derivative and preparation method and application thereof
  • Alpha-pinene derivative and preparation method and application thereof
  • Alpha-pinene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Example 1 (1R,5S)-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)(spiro[indoline-3,4'-piperidine The preparation of ]-2-keto) benzoate

[0137] (1) Preparation of (1R,5S)-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)alcohol

[0138]

[0139] Under the condition of 78° C., 1.32 grams (12 mmol) of active selenium dioxide were dissolved in 10 ml of absolute ethanol solvent, heated to 80° C., and 1.36 grams (10 mmol) of α-pinene was slowly added dropwise thereto for reflux reaction for 3.5 hours, TLC Track and monitor the end point of the reaction, cool and filter, wash the filter residue with a solvent, combine the filtrate and the washing liquid, carry out vacuum distillation under nitrogen protection, and vacuum dry to obtain 0.94 g of a colorless transparent liquid with a yield of 63.1%. The molecular formula is C10H16O, and the molecular weight is for 152.23. 1 HNMR (400MHz, CDCl3) δ5.89 (t, J = 8.7Hz, 1H), 4.10 (s, 2H), 2.45-2.17 (m, 3H), 2.08 (dt, J = 7.9, 3.0Hz, 1H), ...

Embodiment 2

[0149] Example 2 (1R,5S)-(6,6-Dimethylbicyclo[3,1,1]hept-2-en-2-yl)(2-tert-butoxyformyl-1,3,4 , the preparation of 5-tetrahydropyrido[4,3-b]indole) benzoate

[0150] (1) Preparation of (1R,5S)-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)alcohol

[0151]

[0152] Under the condition of 78° C., 1.32 grams (12 mmol) of active selenium dioxide were dissolved in 10 ml of absolute ethanol solvent, heated to 80° C., and 1.36 grams (10 mmol) of α-pinene was slowly added dropwise thereto for reflux reaction for 3.5 hours, TLC Track and monitor the end point of the reaction, cool and filter, wash the filter residue with a solvent, combine the filtrate and the washing liquid, carry out vacuum distillation under nitrogen protection, and vacuum dry to obtain 0.94 g of a colorless transparent liquid with a yield of 63.1%. The molecular formula is C10H16O, and the molecular weight is for 152.23. 1 HNMR (400MHz, CDCl3) δ5.89 (t, J = 8.7Hz, 1H), 4.10 (s, 2H), 2.45-2.17 (m, 3H), 2.08 (dt, J ...

Embodiment 3

[0163] Example 3 Preparation of (1R,5S)-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)methanesulfonate;

[0164] (1) Preparation of (1R,5S)-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)methanol;

[0165]

[0166] Under the condition of 78° C., 1.32 grams (12 mmol) of active selenium dioxide were dissolved in 10 ml of absolute ethanol solvent, heated to 80° C., and 1.36 grams (10 mmol) of α-pinene was slowly added dropwise thereto for reflux reaction for 3.5 hours, TLC Track and monitor the reaction end point, cool and filter, wash the filter residue with a solvent, combine the filtrate and the washing liquid, carry out vacuum distillation under nitrogen protection, and vacuum dry to obtain 0.94 g of a colorless transparent liquid with a yield of 63.1%. The molecular formula is C 10 h 16 O, the molecular weight is 152.23. 1 HNMR (400MHz, CDCl3) δ5.89 (t, J = 8.7Hz, 1H), 4.10 (s, 2H), 2.45-2.17 (m, 3H), 2.08 (dt, J = 7.9, 3.0Hz, 1H), 1.64-1.51(m,2H),0.98(s,6H).

[0167] (2) Prep...

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Abstract

The present invention provides an alpha-pinene derivative with a structural formula shown as a formula I or a formula II. The alpha-pinene derivative is a new derivative obtained by introducing an organic acid into an alpha-pinene backbone molecule by reduction, esterification and the like. In vitro anti-tumor activity studies show that the alpha-pinene derivative has significant liver cancer cell inhibitory effect, and has good prospect in use as a substance for preparation of an anti-tumor compound or a pharmaceutically acceptable salt, a hydrate, a solvate or a predrug thereof, and the formula I and the formula II are as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine and organic synthesis, and more specifically relates to an α-pinene derivative and its preparation method and application. Background technique [0002] Cancer is one of the diseases that pose the greatest threat to human health. The World Health Organization (WHO) pointed out in the "Global Cancer Report 2014" that cancer patients and deaths worldwide are disturbingly increasing, and nearly half of the new cancer cases Occurs in Asia, most of which are in China, where about 50% of new cases of liver and esophageal cancers occur. According to China Daily, Leng Xisheng, chairman of the Chinese Physicians Association (CCS), pointed out that the number of new cases of liver cancer is rising sharply, ranking second in China's cancer-related death rate, becoming the "leader" of the four major provinces of Guangdong, Guangxi, Jiangsu and Zhejiang. The first killer". At the same time, the early sympto...

Claims

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Application Information

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IPC IPC(8): C07D471/10C07D471/04C07C303/28C07C309/66C07C309/67C07C67/08C07C69/618A61P35/00
CPCC07D471/10C07C29/48C07C33/14C07C67/08C07C69/618C07C303/28C07C309/66C07C309/67C07D471/04
Inventor 陈伟强杨梦蝶冯钰吴杰古金华叶连宝
Owner GUANGDONG PHARMA UNIV
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