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Preparation and application of curcumin compound capable of inhibiting activity of human type 1 11beta-hydroxysteroid dehydrogenase

A technology of hydroxysteroids and dehydrogenase inhibitors, which is applied in the field of medicine, can solve the problems of poor solubility and low oral bioavailability, and achieve the effect of good solubility

Active Publication Date: 2014-04-02
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds are generally poorly soluble, difficult to administer by injection, and have low oral bioavailability

Method used

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  • Preparation and application of curcumin compound capable of inhibiting activity of human type 1 11beta-hydroxysteroid dehydrogenase
  • Preparation and application of curcumin compound capable of inhibiting activity of human type 1 11beta-hydroxysteroid dehydrogenase
  • Preparation and application of curcumin compound capable of inhibiting activity of human type 1 11beta-hydroxysteroid dehydrogenase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation and identification of the compound of formula (1)

[0032] Weigh 1.0g (7.5mM) piperidone hydrochloride and 1.97g (15mM) p-chlorobenzaldehyde in a round bottom flask, add 10ml absolute ethanol to dissolve. Then, in an ice bath, slowly drop 5ml of concentrated hydrochloric acid into the reaction solution. After magnetic stirring and heating to reflux for 6 hours, a large amount of yellow solid precipitated. After cooling the suspension to room temperature, filter with a sand core funnel, collect the filtered solid, and wash it with absolute ethanol 3 times. After drying under vacuum at 30°C overnight, 1.95 g of a yellow powder was obtained. After purification by silica gel column chromatography, 98% of the compound was obtained with a yield of 65.7%. 1 H NMR (500MHz, DMSO) δ: 10.02 (s, 2H), 7.99 (s, 2H), 7.64 (dd, J=6.6, 2.2 Hz, 2H), 7.57-7.43 (m, 6H), 4.35 (d, J=1.8Hz, 4H). 13 C NMR (75MHz, DMSO) δ: 182.0, 135.7, 133.9, 131.5, 131.4, 130.6, 129.8, 1...

Embodiment 2

[0033] Example 2: Curcumin derivatives inhibit the reducing activity of 11β-HSD1 in rat hepatocytes and testicular stromal cells

[0034] Separation of hepatocytes and testicular stromal cells: use CO 2 After the rats were killed by asphyxiation method, the testes were removed to extract and purify the mesenchymal cells. The method refers to (Salva A, et al. J Androl. 2001, 22, 665-671). The purity of the mesenchymal cells was determined by the 3β-hydroxysteroid dehydrogenase activity histochemical staining method (with 0.4mM cholanolide as the steroid substrate), which can stain more than 95% of mature mesenchymal cells; liver parenchymal cells The separation of using Pertoft and The method (Cell Separation: Methods and Selected Applications.pp: 1-23, Academic Press, Orlando, F, 1987) is to infuse the rat liver with calciumfree buffer solution in situ and disperse it in 0.05% collagenase solution. Hepatic parenchymal cells were obtained by density gradient centrifugation and pu...

Embodiment 3

[0037] Example 3: Curcumin compound preparation for preventing and treating human type 2 diabetes

[0038] Compound YD prepared according to the method of Example 1 was added with excipients in a ratio of 5:1 to the weight ratio of the excipients, and then granulated and compressed. For liquid preparations, compound YD prepared according to the method of Example 1 can then be added with water for injection according to the conventional injection preparation method, and the injection can be prepared after precision filtration, potting and sterilization.

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Abstract

The invention relates to a curcumin compound shown as the formula (1), a preparation method of the compound, and application of the compound as an inhibitor of type 1 11beta-hydroxysteroid dehydrogenase (11beta-HSD1) in a medicine for preventing and treating type 2 diabetes mellitus.

Description

Technical field [0001] The present invention belongs to the technical field of medicine. Specifically, the present invention relates to a curcumin compound that can inhibit the activity of human type 1 11β-hydroxysteroid dehydrogenase, its preparation method and its active ingredient in the prevention and treatment of type 2 Application of diabetes medicine. Background technique [0002] Diabetes is an endocrine metabolic disease characterized by high blood sugar and diabetes caused by insufficient insulin secretion in the body or insulin resistance. It is often accompanied by atherosclerotic cardiovascular disease, diabetic nephropathy, neuropathy, lower extremity ulcers, eye diseases such as Various complications such as cataracts and retinopathy. At present, diabetes has become the third most serious disease that seriously endangers human health after cardiovascular and cerebrovascular diseases and cancer. Clinically, diabetes is divided into: 1) Type 1 diabetes: pancreatic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/68A61K31/4412A61P3/10
Inventor 苏志坚葛仁山黄亚东项琪张齐好
Owner JINAN UNIVERSITY
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