Tryptophan hydroxylase-1 inhibitor ursolic acid derivatives as well as preparation method and application thereof

A technology of tryptophan hydroxylase and ursolic acid, which is applied in the direction of steroids, organic chemistry, drug combination, etc., to increase the bone density of the spine and prevent osteoporosis

Inactive Publication Date: 2014-07-23
南京惠特莱医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports involving ursol

Method used

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  • Tryptophan hydroxylase-1 inhibitor ursolic acid derivatives as well as preparation method and application thereof
  • Tryptophan hydroxylase-1 inhibitor ursolic acid derivatives as well as preparation method and application thereof
  • Tryptophan hydroxylase-1 inhibitor ursolic acid derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0040] Example 1

[0041] For the preparation of compound 2, the reaction formula is:

[0042]

[0043] Weigh 13.25g (28.8mmol) of ursolic acid and dissolve it in 150.0mL N,N-dimethylacetamide or N,N-dimethylformamide at 90℃, and slowly add 10.0mL hydrogen peroxide / sodium tungstate / For the mixed solution of disodium hydrogen phosphate / sodium dihydrogen phosphate (12.5 / 0.5 / 0.2 / 0.2, molar equivalent), the time for dropping is controlled at about 1 hour. After reacting for one hour, it was cooled, poured into cold water, extracted with ethyl acetate, washed, dried with anhydrous sodium sulfate, and evaporated to remove the solvent to obtain 3.92 g of 3-carbonylursolic acid 2, yield: 86%. Product characterization, the data is: 1 H NMR(300MHz, CDCl 3 )δ: 5.30(s, 1H), 2.76(d, J=15.0Hz, 1H), 2.28–2.14(m, 3H), 2.09–1.97(m, 2H), 1.84–1.69(m, 3H), 1.64 -1.47(m, 6H), 1.33(d, J=2.8Hz, 3H), 1.31(s, 2H), 1.28(d, J=2.1Hz, 3H), 1.23(s, 3H), 1.18(s, 3H), 0.99(s, 3H), 0.97(s, 2H), 0.95(s, 4H), 0...

Example Embodiment

[0443] Example 2 Specific experimental examples of ursolic acid derivatives:

[0444] 1) In vitro inhibition of 5-HT synthesis experiment

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Abstract

The invention discloses tryptophan hydroxylase-1 inhibitor ursolic acid derivatives as well as a preparation method and application thereof and belongs to the technical field of the biological medicine. Proven by experiments, some ursolic acid derivatives are capable of specifically inhibiting the activity of Tph-1 without affecting that of Tph-2, and meanwhile, the bone mineral density data of vertebra also indicate that the bone mineral density of the vertebras of rats is obviously increased, and obviously, the ursolic acid derivatives are capable of effectively preventing osteoporosis and can be widely applied to preparing medicines for treating the osteoporosis.

Description

technical field [0001] The invention belongs to the technical field of ursolic acid derivatives, and in particular relates to a tryptophan hydroxylase-1 inhibitor ursolic acid derivative and its preparation method and application. Background technique [0002] With the aging of the population, the prevalence of osteoporosis (OP) is increasing year by year. Characterized by bone resorption at a faster rate than bone formation, it is a worldwide health problem, especially in menopausal women. Osteoporosis currently affects more than 10 million people in the United States alone, and that number could reach 14 million by 2020. According to statistics, there were about 2.5 million patients in Europe in 2010, and about 84 million patients with osteoporosis in China. So many osteoporosis patients not only bring great pressure to people's life, but also cause a very serious economic burden in today's society. [0003] 5-hydroxytryptamine (5-hydroxytryptamine, 5-HT) is an ancient ...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61P19/10
Inventor 李建新
Owner 南京惠特莱医药科技有限公司
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