Enyne bromide compounds 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: 2013-01-02
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Enyne bromide compounds and preparation method and use thereof
  • Enyne bromide compounds and preparation method and use thereof
  • Enyne bromide compounds and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037](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

[0038] 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.

[0039] 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); amon...

Embodiment 2

[0044] (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)

[0045] Step 3: Preparation of compound X31: 40 g of ether extract 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 Me...

Embodiment 3

[0050] Preparation of sodium (17E,21E)-22-bromo-doco-17,21-diene-9,11,19-triynoate (compound X1N)

[0051] Step 4: Dissolving compound X1 obtained in Example 1 in tert-butanol and reacting with sodium tert-butoxide to obtain (17E, 21E)-22-bromo-docos-17,21-diene-9,11, Sodium 19-triynoate;

[0052] (17E,21E)-22-Bromo-doco-17,21-diene-9,11,19-triynoate sodium (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 present invention relates to enyne bromide compounds (with structural formula shown below) and preparation method and use thereof. Vitro biological activity test shows such compounds significantly inhibit the activity of pancreatic lipase, and can be used as a new drug lead compound for prevention or therapeutic treatment of obesity and related metabolic disorders and used for the preparation of the drug for clinical treatment of common obesity and related metabolic diseases.

Description

technical field [0001] 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 [0002] 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 genetic factors, environmental factors, eating habits, etc. Among them, high-fat diet is an important cause of obesity. Due to the development of the economy and the improvement of living standards, insufficient exercise and relative excess energy intake have gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/52C07C51/43C07C51/41C07C69/65C07C67/14C07C233/09C07C231/02A61K31/201A61K31/231A61K31/16A61K31/165A61P3/04A61P3/10A61P3/06A61P1/16
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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