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Flavanol-fatty alcohol hybrids as well as pharmaceutical composition, preparation method and application thereof

A technology of flavanols and fatty alcohols, applied in the directions of drug combination, application, pharmaceutical formulation, etc.

Pending Publication Date: 2020-11-24
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

So far, there are no reports of tsaokoflavanols A–S (tsaokoflavanols A–S, 1-19) in the prior art, and no reports of compounds 1-19 and their pharmaceutical compositions as PTP1B and α-glucosidase inhibitors. Reports, and application reports in the preparation of hypoglycemic drugs or health food

Method used

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  • Flavanol-fatty alcohol hybrids as well as pharmaceutical composition, preparation method and application thereof
  • Flavanol-fatty alcohol hybrids as well as pharmaceutical composition, preparation method and application thereof
  • Flavanol-fatty alcohol hybrids as well as pharmaceutical composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of Compounds 1-19:

[0030] Dried fruit of Tsaoko, crushed, reflux extracted with 50% ethanol (100L) three times, each time for 2h, combined ethanol extracts, recovered ethanol under reduced pressure to obtain extract, the extract was dispersed in water, extracted with ethyl acetate, and then concentrated The ethyl acetate extract was obtained, and then the ethyl acetate extract (Fr.A) was subjected to silica gel column chromatography, and methanol-chloroform (0:100, 5:95, 10:90, 20:80 and 40:60, v / v) Seven fractions of Fr.A-1~Fr.A-7 were obtained by gradient elution of eluent; Fraction Fr.A-6 was subjected to MCICHP20P gel column chromatography (methanol-water, 40:60, 60:40, 80:20 and 100:0) to obtain four subfractions Fr.A-6-1~Fr.A-6-4; Fr.A-6-2 was subjected to silica gel column chromatography (MeOH-CHCl 3 , 2:98) to obtain three subfractions Fr.A-6-2-1~Fr.A-6-2-3; Fr.A-6-2-2 was passed through Sephadex LH-20 (methanol-chloroform, 50:50), silica gel col...

Embodiment 2

[0251] PTP1B and α-glucosidase inhibitory activity.

[0252] 1 Materials and methods

[0253] 1.1 Materials

[0254] α-glucosidase (Sigma Aldrich, St.Louis, MO, USA); phosphate buffer (≥99%, Meilun Bio, Dalian); p-nitrophenyl-α-D-glucopyranose (≥99%) %, Yuanye Biology, Shanghai); acarbose (≥98%, Bayer Pharmaceuticals, Beijing); PTP1B (protein tyrosine phosphatase) was purchased from Sino Biological (Wayne, PA, USA); suramin sodium was purchased from From ACROS (New Jersey USA)

[0255] 1.2 Instruments

[0256] Flex Station 3 desktop multifunctional microplate reader (Bio-RAD 680, USA); analytical balance (AG135, Metler Toledo, China); thermostat box (DHP-9082, Shanghai).

[0257] 1.3 Experimental process

[0258] PTP1B inhibitory activity was performed according to the inventors' previous studies. Briefly, the working buffer (workingbuffer, WB) was composed of 3-(N-morpholino)propanesulfonic acid (MOPS, 722.02mg), dithiothreitol (DTT, 30mg), EDTA (25.7mg), It is prepare...

preparation Embodiment 1～19

[0271] In the following preparation examples, conventional reagents are selected, and preparations are prepared according to existing conventional methods. This example only reflects that at least one of the compounds 1 to 19 of the present invention can be prepared into different preparations. For specific reagents and The operation is not specifically limited:

[0272] 1. Dissolve at least one of the compounds 1 to 19 prepared in Example 1 with DMSO, add water for injection according to conventional methods, fine filter, potting and sterilizing to make an injection, and the concentration of the injection is 0.5 ~5mg / mL.

[0273] 2. After dissolving at least one of the compounds 1 to 19 prepared in Example 1 with DMSO, dissolve it in sterile water for injection, stir to dissolve it, filter it with a sterile suction filter funnel, and then sterilize it. filtered, divided into ampoules, freeze-dried at low temperature and sealed aseptically to obtain a powder injection.

[02...

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Abstract

The invention provides 19 novel flavanol-fatty alcohol hybrids, as shown in a structural formula (I), tsaokoflavanols A-S 1-19, as well as a preparation method, pharmaceutical composition and application thereof, and relates to the technical field of medicines. The compound disclosed by the invention has obvious inhibitory activity on PTP1B and alpha-glucosidase, can form the pharmaceutical composition together with a medicinal carrier or an excipient, and can be used for preparing PTP1B and alpha-glucosidase inhibitor drugs, hypoglycemic drugs or health-care foods.

Description

Technical field: [0001] The invention belongs to the technical field of medicines. Specifically, it involves 19 new flavanol-fatty alcohol hybrids, tsaokoflavanols A-S (tsaokoflavanols A-S, 1-19), their preparation methods and applications, pharmaceutical compositions and their applications. Background technique: [0002] Type 2 diabetes is a chronic metabolic disease characterized by inappropriate postprandial hyperglycemia, resulting from pancreatic β-cell dysfunction and insulin resistance in the body. In 2017, more than 400 million people worldwide suffered from type 2 diabetes, and this number is expected to reach 600 million by 2045. The clinical methods used to treat type 2 diabetes mainly include exogenous injection of insulin and oral hypoglycemic drugs. According to different modes of action, commonly used oral hypoglycemic drugs can be divided into biguanides, α-glucosidase inhibitors, insulin secretion enhancers, insulin sensitizers, glucagon-like peptide 1 rec...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/352A61P3/10
CPCC07D493/04A23L33/105A61P3/10A23V2002/00A23V2200/328A23V2250/21A23V2300/14Y02A50/30
Inventor 耿长安何小凤陈纪军胡敬李天泽黄晓燕马云保张雪梅
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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