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Tropinone derivative and its preparation method and application

A kind of technology of tropinone derivative, acetoxy tropane, applied in the field of preparation of new compound

Active Publication Date: 2015-09-02
HERBALIFE LEISHUO HUNAN NATURAL PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, there is no relevant research on applying tropinone derivatives to antidiabetic drugs

Method used

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  • Tropinone derivative and its preparation method and application
  • Tropinone derivative and its preparation method and application
  • Tropinone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 genipin derivative

[0036] 1.1 Instruments and reagents

[0037] Nuclear magnetic resonance spectrum adopts Brucker400MHz ADVANCE DMX500 type nuclear magnetic resonance instrument to measure (TMS is internal standard, CDC1 3 is the solvent); ESI mass spectrum was determined by Esquire600 (Brucker, Germany) mass spectrometer.

[0038] The column chromatography silica gel is 200-300 mesh (Qingdao Ocean Chemical Factory), and the chemical reagents are domestic analytical reagents without further purification before use.

[0039] 1.2 Preparation of tropin ketone

[0040] Compound 1 (see attached figure 1 ) preparation: Add 5.00g of 6-hydroxytropinone, 50mL of dichloromethane, and 3mL of triethylamine in a 250mL three-neck flask, and add 5mL of benzoyl chloride dropwise under nitrogen protection in an ice bath, and stir overnight at room temperature. The solvent was removed by rotary evaporation under reduced pressure, and the residue was ...

Embodiment 2

[0058] Example 2 Anti-diabetic bioactivity detection of tropinone derivatives

[0059] Dipeptidyl peptidase IV inhibitors are new hypoglycemic drugs that have attracted much attention at present. Studies have shown that dipeptidyl peptidase IV inhibitors can promote the release of insulin from β cells, increase the synthesis of insulin in β cells, and inhibit the secretion of glucagon at the same time, without hypoglycemia events and fewer side effects. Type 2 diabetes has very good prospects.

[0060] 2.1 Experimental reagents

[0061] Rosiglitazone (Sigma, R2408)

[0062] TransIT-293 Transfection Reagent (Mirus, MIR2706)

[0063] Dimethylsulfoxide (Sigma, Cat.No.154938-1L, Lot.No.52396AK)

[0064] 384-well plate (384-magnetic separator) (Greiner, 781080)

[0065] Dipeptidyl peptidase IV (Sigma, Cat#D4943, Lot#080M1723)

[0066] Dipeptidyl peptidase IV – globulin TM Protease (Promega, Cat#G8351, Lot#320119)

[0067] 384-well plate (PerkinElmer, OptiPlate-384, White Op...

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Abstract

The invention belongs to the preparation field of a new compound, and particularly relates to a tropinone derivative, and a preparation method and an application of the tropinone derivative. The tropinone derivative and pharmaceutically acceptable salt of the tropinone derivative have the structural formula shown by a general formula I, wherein R2 is selected from alkyl group with 1-6 carbon atoms, aromatic group with 1-20 carbon atoms, heterocyclic ring with 1-20 carbon atoms, and amino group; X is selected from alkyl group with 1-6 carbon atoms, aromatic group with 1-20 carbon atoms, heterocyclic ring with 1-20 carbon atoms, methylsulfonyl and p-tosyl; or R1 is selected from alkyl group with 1-6 carbon atoms, aromatic group with 1-20 carbon atoms, and heterocyclic ring with 1-20 carbon atoms. The tropinone derivative can be used for preparing a medicine for treating II type diabetes mellitus.

Description

technical field [0001] The field of preparation of new compounds of the present invention relates to tropinone derivatives and their preparation methods and applications. Background technique [0002] According to statistics from the World Health Organization in 2011, there are 366 million people with diabetes worldwide, most of whom are type II diabetes, and about 4.6 million people die from the disease and its complications every year. The main drugs currently used to treat diabetes are sulfonylureas, thiazolidinediones and metformin. However, for many patients, these drugs make it difficult to maintain blood sugar at a normal level. Therefore, it is of great significance to invent a new type of drug to treat diabetes. [0003] Alkaloids are mainly a class of secondary metabolites in plants that are derived from amino acids, contain nitrogen, and have nitrogen atoms in a ring structure with significant biological activity. Tropane alkaloids are a class of alkaloids with...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D451/04C07D451/02A61K31/46A61P3/10
Inventor 郑群怡谢朝阳李志伟鲍志超王建南
Owner HERBALIFE LEISHUO HUNAN NATURAL PROD