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Indole kind compound with insuline sensitizing activity and its preparation method and use

A compound and indole technology, applied in the field of indole compounds and their preparation, can solve the problems of patient weight gain, liver toxicity and the like

Inactive Publication Date: 2006-01-25
GUIYANG MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Several glitazone insulin sensitizers on the market can cause different degrees of liver toxicity, and some glitazone insulin sensitizers can also cause patients to gain weight

Method used

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  • Indole kind compound with insuline sensitizing activity and its preparation method and use
  • Indole kind compound with insuline sensitizing activity and its preparation method and use
  • Indole kind compound with insuline sensitizing activity and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1: 2-methyl-1-(4-chlorobenzoyl)-5-benzyloxy-1H-indole-3-acetic acid (compound 1)

[0106] Dissolve 12.9g (40.8mmol) of sodium p-benzyloxyphenylhydrazine sulfonate in 576mL of water, raise the temperature to 55-65°C, add 476mL of ethanol after 15min, cool down to 20-25°C, add 5mL of p-chlorobenzoyl chloride, from the reaction solution Start timing when it thickens, stir for 1 hour, then raise the temperature to 75-80°C, and continue stirring for 1 hour. Cool down to 65±2°C, add 1N NaOH solution dropwise, adjust pH=9-10, stir for about 20 minutes until the pH remains unchanged, cool down to below 20°C, wash with suction to neutrality, and dry to obtain N-p-chlorobenzene Formyl-N-p-benzyloxyphenylhydrazine is a khaki solid.

[0107] 1 g (2.84 mmol) of N-p-chlorobenzoyl-N-p-benzyloxyphenylhydrazine was dissolved in 100 mL of absolute ethanol, and under ice bath conditions, dry HCl gas was introduced into the reaction liquid, and left at room temperature after satur...

Embodiment 2

[0109] Example 2: 2-methyl-1-(4-chlorobenzoyl)-5-benzyloxy-1H-indole-3-acetic acid methyl ester (compound 2)

[0110] 10mL CH 3 OH was cooled to -10°C in an ice-salt bath, and 0.6mL (15.9mol) SOCl was added dropwise 2 , Control the drop rate so that the internal temperature is less than -5°C. After dropping, add 2.52g (5.82mmol) of 2-methyl-1-(4-chlorobenzoyl)-5-benzyloxy-indole-3-acetic acid, raise the temperature to 25°C, and continue to stir until it is completely dissolved Then, stir at 0°C for another 1 h. The reaction solution was evaporated to dryness, dissolved in ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate to obtain 0.19 g of an oily liquid. Petroleum ether:ethyl acetate=3:1 was used as the eluent, and the title compound was obtained as an oil 1.78g by silica gel column chromatography. Yield 68%. 1 H NMR (CDCl 3 ): δ=2.39(s, 3H), 3.47(s, 3H), 3.68(s, 2H), 5.07(s, 2H), 6.75(dd, J=8.8Hz, 2.4Hz, 1H), 6.86(d , J=8.8Hz, 1H), 7...

Embodiment 3

[0111] Example 3: 2-methyl-1-(4-fluorobenzoyl)-5-benzyloxy-1H-indole-3-acetic acid (compound 3)

[0112] Using 4-fluorobenzoyl chloride as a raw material, the title compound was prepared as a white solid according to the method of Example 1. The total yield is 17.8%. 1 H NMR (CDCl 3 ): δ=2.39(s, 3H), 3.68(s, 2H), 5.07(s, 2H), 6.75(dd, J=8.8Hz, 2.4Hz, 1H), 6.86(d, J=8.8Hz, 1H ), 7.05 (d, J = 2.4Hz, 1H), 7.26-7.47 (m, 7H), 7.74 (d, J = 8.6Hz, 2H).

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Abstract

The invention discloses indole compounds having insulin-sensitizing activity, process for preparation and use, wherein the compounds and salts have the structural formula of (I), wherein R1 is hydrogen atom, substituted C1-C6 alkyl, substituted aryl alkyl, substituted aromatic heterocyclic alkyl, R2 is alkyl acyl, substituted cycloalkyl acyl, substituted aryl acyl, R3 is hydrogen atom or substituted C1-6 alkyl, R4 is hydrogen atom or substituted C1-6 alkyl, n=0, 1 or 2.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and type 2 diabetes therapeutics, in particular to an indole compound with insulin-sensitizing activity, a preparation method and application thereof. technical background [0002] Type 2 diabetes mellitus is a chronic wasting disease, which is caused by insulin resistance or relatively insufficient insulin secretion in the human body, which causes the metabolic disorder of sugar, protein, fat, water and electrolyte in the human body, so that liver glycogen and muscle glycogen cannot be synthesized , leading to elevated blood sugar and diabetes, with time and the prolongation of the disease, it is easy to be complicated by systemic microvascular and macrovascular lesions, and can lead to chronic lesions of the heart, brain, kidney, nerves, eyes and other organs, which can be life-threatening in severe cases. With the improvement of people's living standards, diabetes has become the third fatal ...

Claims

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Application Information

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IPC IPC(8): C07D209/42C07D401/12C07D413/12A61K31/404A61K31/422A61K31/4439A61P3/10
Inventor 汤磊李煜杨玉社王建塔张旭
Owner GUIYANG MEDICAL UNIVERSITY
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