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20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative and pharmaceutical composition thereof

A technology of dammarane and its derivatives, which is applied in the field of 20S, 24R-epoxy-dammarane-3β, 12β, 25-triol derivatives and their pharmaceutical compositions, which can solve endogenous insulin secretion deficiency, insulin Lack of, poor effect and other problems

Pending Publication Date: 2021-12-03
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Type II diabetes is a condition in which the body can produce insulin, but due to impaired insulin sensitivity, insufficient secretion of endogenous insulin or poor effect, etc., it leads to a relative lack of insulin

Method used

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  • 20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative and pharmaceutical composition thereof
  • 20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative and pharmaceutical composition thereof
  • 20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1. Synthesis method of 20S,24R-epoxy-3β-o-benzoic acid benzoyl-12-carbonyl-dammaran-25-ol (1) [compound 1]:

[0027] 20S,24R-epoxy-dammarane-3β,12β,25-triol (30mg, 0.06mmol) was dissolved in DCM, and PCC (25.8mg, 0.12mmol) was added under stirring, and reacted at room temperature, and the reaction was detected by TLC. The reaction solution was filtered through diatomaceous earth, washed with dichloromethane, the filtrate was collected, and the solvent was recovered under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (ethyl acetate-petroleum ether, 35:65, v / v) to obtain the target compound 20S, 24R-epoxy-12-carbonyl-dammarane-3β,25-diol (20% yield).

[0028] 20S, 24R-epoxy-12-carbonyl-dammarane-3β, 25-diol (12.0mg, 0.03mmol) was dissolved in 0.6mL pyridine, after adding phthalic anhydride (22.2mg, 0.15mmol) at 80 The reaction was refluxed at ℃. After 72 hours, the reaction was stopped. After cooling to room temperatu...

Embodiment 2

[0049] Inhibitory activity of 20S,24R-epoxy-dammarane-3β,12β,25-triol derivatives 1 and 2 (compounds 1 and 2) against α-glucosidase and PTP1B.

[0050] 1 Materials and methods

[0051] 1.1 Materials

[0052] α-glucosidase (Sigma Aldrich, USA); p-nitrophenyl-α-D-glucopyranose (Yuanye Biotechnology, Shanghai); acarbose (Bayer Pharma, Beijing); phosphate buffer (PB , Na 2 HPO 4 and NaH 2 PO 4 2H 2 O, Dalian Meilun Biological Co., Ltd.), sodium carbonate (Dalian Meilun Biological Co., Ltd.), 3-(N-morpholino) propanesulfonic acid (MOPS, Beijing Suolaibao Technology Co., Ltd.), dithiothreitol (DTT, Dalian Meilun Biotechnology Co., Ltd.), sodium ethylenediaminetetraacetate (EDTA, Beijing Suolaibao Technology Co., Ltd.); bovine serum albumin (BSA, amresco), disodium p-nitrophenylphosphonic acid (p -NPP, Beijing Suolaibao Technology Co., Ltd.), sodium suramin (Acros organics), PTP1B enzyme (SINO, 10304-H07E).

[0053] 1.2 Instruments

[0054] Flex Station 3 desktop multifuncti...

preparation Embodiment

[0067] 1. Take compounds 1 and 2, dissolve them with a small amount of DMSO, add water for injection as usual, fine filter, potting and sterilize to make an injection.

[0068] 2. Take compounds 1 and 2, dissolve them with a small amount of DMSO, dissolve them in sterile water for injection, stir to dissolve, filter with a sterile suction filter funnel, and then sterile fine filter. After freeze-drying, aseptically melt-seal to obtain powder injection.

[0069] 3. Take compounds 1 and 2, and add excipients according to the weight ratio of them to the excipients at a ratio of 9:1 to make a powder.

[0070] 4. Take compounds 1 and 2, add excipients according to the weight ratio of them and excipients at a ratio of 5:1, and make compressed tablets.

[0071] 5. Take compounds 1 and 2 and make oral liquid according to the conventional oral liquid preparation method.

[0072] 6. Take compounds 1 and 2, add excipients according to the weight ratio of them and excipients at a ratio ...

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PUM

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Abstract

The invention provides a 20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative (1 and 2) as shown in a structural formula (I), a pharmaceutical composition and a preparation method of the 20S, 24R-epoxy-dammarane-3 [beta], 12 [beta], 25-triol derivative, and application of the derivative 1 and 2 and the pharmaceutical composition thereof in preparation of [alpha]-glucosidase and PTP1B inhibitors and in preparation of medicines for treating type II diabetes mellitus and reducing blood sugar. The invention belongs to the technical field of medicines. The triol derivative disclosed by the invention has relatively good inhibitory activity on the [alpha]-glucosidase and PTP1B.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to 20S, 24R-epoxy-dammarane-3β, 12β, 25-triol derivatives 1 and 2, a pharmaceutical composition using them as active ingredients, a preparation method, and derivatives 1 and 2 and the application of the pharmaceutical composition thereof in the preparation of α-glucosidase and PTP1B inhibitory drugs and in the preparation of drugs for treating type II diabetes, hypoglycemic drugs or health food. Background technique [0002] Diabetes mellitus is a group of common endocrine and metabolic diseases caused by the interaction of genetic and environmental factors, mainly due to the absolute or relative deficiency of insulin secretion and the decreased sensitivity of target cells to insulin. Disorders of protein metabolism. According to the report of the World Health Organization (WHO), the number of people with diabetes worldwide continues to rise, and it is predicted that ...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61K31/575A61P3/10A23L33/00
CPCA61K31/58A61K31/575A61P3/10A23L33/00A23V2002/00A23V2200/328
Inventor 陈纪军杨晓烔李天泽耿长安
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI