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

A compound, curcumin technology, 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: 2012-05-30
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] Embodiment 1: Preparation and identification of compounds of formula (1)

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

Embodiment 2

[0033] Example 2: Curcumin Derivatives Inhibit the Reducing Activity of Rat Hepatocytes and Leydig Cells 11β-HSD1

[0034] Isolation of hepatocytes and Leydig cells: CO 2 After the rats were killed by asphyxiation, the testes were removed to extract and purify the interstitial cells. For the method, refer to (Salva A, et al. J Androl. 2001, 22, 665-671). The purity of interstitial cells is determined by histochemical staining method for 3β-hydroxysteroid dehydrogenase activity (using 0.4mM cholanolone as a steroid substrate), which can stain more than 95% of mature interstitial cells; hepatic parenchymal cells Separation using Pertoft and The method (Cell Separation: Methods and Selected Applications.pp: 1-23, Academic Press, Orlando, F, 1987), that is, in situ perfusion of calciumfree buffer in the rat liver, dispersed in 0.05% collagenase solution, Hepatic parenchymal cells were purified by density gradient centrifugation.

[0035] Preparation of microsomal protein: mous...

Embodiment 3

[0037] Embodiment 3: be used for the curcumin compound preparation of prevention and treatment human type 2 diabetes

[0038] Compound YD prepared according to the method of Example 1 was added with excipients according to the weight ratio of the compound YD to the excipients at a ratio of 5:1, and then granulated and compressed into tablets. For liquid preparations, compound YD can be prepared according to the method of Example 1, and then add water for injection according to the conventional injection preparation method, and then make injections after fine 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 invention belongs to the field of medical technology, in particular, the invention relates to a curcumin compound capable of inhibiting the activity of human type 1 11β-hydroxysteroid dehydrogenase, its preparation method and its use as an active ingredient in the prevention and treatment of type 2 Application in diabetes medicine. Background technique [0002] Diabetes mellitus is an endocrine metabolic disease characterized by hyperglycemia and diabetes caused by insufficient insulin secretion or insulin resistance in the body, often accompanied by atherosclerotic cardiovascular disease, diabetic nephropathy, nervous system disease, lower extremity ulcers, eye diseases Cataract, retinopathy and other complications. At present, diabetes has become the third major disease that seriously endangers human health after cardiovascular and cerebrovascular diseases and cancer. Clinically, diabetes is divided into: 1) Type 1 diabetes: destruction of panc...

Claims

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Application Information

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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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