Bromide acetylene compound and preparation method and use thereof

A technology of acetylenic compounds and alkenyl bromide, which is applied in the field of medicine and can solve problems such as unseen biological activity research reports

Inactive Publication Date: 2014-10-01
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After literature search, there is no research report on the biological activity of this type of compound in this respect

Method used

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  • Bromide acetylene compound and preparation method and use thereof
  • Bromide acetylene compound and preparation method and use thereof
  • Bromide acetylene compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (17E,21E)-22-bromo-doco-17,21-diene-9,11,19-triynoic acid (compound X1), (E)-18-bromo-octadec-17- En-5,7,15-triynoic acid (compound X2) and (13E,17E)-18-bromo-octadeca-13,17-diene-5,7,15-triynoic acid (compound X3) preparation of

[0040] Step 1: Extraction: China Guangxi Weizhou Island sponge (Xestospongia testudinaria) dry weight 4kg, repeated ultrasonic extraction 3 times with acetone 3L, the extracts were combined and then concentrated under reduced pressure, the obtained crude extract was suspended in 1500ml 1N NaCl solution, and The suspension was repeatedly extracted 3 times with 1500 ml of ether, and the obtained extracts were combined and concentrated under reduced pressure to obtain 40 g of ether extract.

[0041] Step 2: Preparation of compounds X1, X2 and X3: The diethyl ether extract obtained in step 1 was subjected to silica gel column chromatography, and eluted with petroleum ether / diethyl ether gradient (100:0→90:10→80:20→50: 50→20:80→10:90→0:100); amo...

Embodiment 2

[0046] (17E,21E)-22-Bromo-doco-17,21-diene-9,11,19-triynoic acid methyl ester (compound X11), (E)-18-bromo-octadecyl- 17-ene-5,7,15-triynoic acid methyl ester (compound X21) and (13E,17E)-18-bromo-octadec-13,17-diene-5,7,15-triynoic acid Preparation of methyl ester (compound X31)

[0047] Step 3: Preparation of compound X31: Ether extract 40g was subjected to 200-300 mesh silica gel column chromatography, and petroleum ether / ether 100:0→90:10→80:20→50:50→20:80→10:90 → 0:100 gradient elution, the amount of each gradient is 5000ml; among them, petroleum ether / diethyl ether 50:50 eluent concentrate was obtained 2.0g, this part was methylated with diazomethane first, and then petroleum ether / chloroform / Methanol was eluted at 2:1:1, followed by silica gel column chromatography (petroleum ether / ether 100:0→90:10→80:20→70:30) to obtain (17E,21E)-22-bromo-20 Dicarba-17,21-diene-9,11,19-triynoic acid methyl ester X11 11.3mg; (E)-18-bromo-octadec-17-ene-5,7,15-triynoic acid Methyl e...

Embodiment 3

[0052] Preparation of (17E,21E)-22-bromo-doco-17,21-diene-9,11,19-triynoate sodium (compound X1N)

[0053] Step 4: The compound X1 obtained in Example 1 was dissolved in tert-butanol and reacted with sodium tert-butoxide to obtain (17E,21E)-22-bromo-docosa-17,21-diene-9,11, Sodium 19-triynoate;

[0054] Sodium (17E,21E)-22-bromo-doco-17,21-diene-9,11,19-triynoate (compound X1N) has the following physical and chemical properties: colorless jelly, and the spectral data are as follows :C 22 h 26 BrO 2 Na; 1 H NMR (300MHz, CDCl 3 )δ H 6.63(d,J=14.0Hz,H-22),6.30(dd,J=14.0,2Hz,H-21),6.17(dt,J=15.5,7.0Hz,H-17),5.55(dd,J =15.5,2.0Hz,H-18),2.35(t,J=7.0Hz,H-2),2.25(t,J=7.0Hz H-8,H-13),2.14(m,H-16) ,1.63(m,H-3),1.51(m,H-7,H-14,H-15),1.45(m,H-4),1.39(m,H-6),1.35(m,H -5).

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Abstract

The invention relates to a bromide acetylene compound shown in a structural general formula and a preparation method and use thereof. The compound has obvious inhibitory activity on pancrelipase by an in-vitro biological activity test. The compound can be used as a lead compound for developing a novel drug for preventing or treating obesity and related metabolic diseases, and also can be used for preparing a drug for treating common frequently-occurring obesity and related metabolic diseases in clinic.

Description

[0001] This application is a divisional application of an invention patent application with an application date of June 29, 2011, an application number of 201110180360.0, and an invention title of "Brominated Enyne Compounds and Their Preparation and Use". technical field [0002] The invention relates to the technical field of medicine, in particular to a class of brominated enyne compounds and a preparation method and use thereof. This type of compound has obvious inhibitory activity on pancreatic lipase, and can be used as a class of lead compounds for the development of new drugs for the prevention or treatment of obesity and related metabolic diseases, and can also be used to prepare and treat common clinical obesity and its related diseases. Drugs for metabolic diseases. Background technique [0003] In the past 20 years, the incidence of obesity has been increasing all over the world, especially in developed countries. There are many reasons for obesity, such as gene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/201A61K31/231A61P3/04A61P3/10A61P3/06A61P1/16
Inventor 王贺瑶郭跃伟王婷蔡由生孙鹏
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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