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New application of tetrahydro isoquinoline alkaloid

A technology of tetrahydroisoquinoline and alkaloids, which is used in drug combination, analysis by chemical reaction of materials, and material analysis by observing the effect on chemical indicators.

Inactive Publication Date: 2017-06-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Artificial synthesis of small molecule α-amylase inhibitors is still blank

Method used

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  • New application of tetrahydro isoquinoline alkaloid
  • New application of tetrahydro isoquinoline alkaloid
  • New application of tetrahydro isoquinoline alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis and identification of the screened compounds of the present invention

[0025] All reagents were commercially pure or analytically pure.

[0026] The basic process of the reaction: the total synthesis of tetrahydroisoquinolines can use phenylethylamine and phenylacetic acid or amino acids as intermediate raw materials for N-acylation condensation, and then obtain dihydroisoquinolines through Bischler-Napieralski reaction, and then After imine reduction and salt-forming reaction, tetrahydroisoquinoline alkaloid salts are finally obtained. The intermediate raw materials can introduce various substituents on the ring by changing the substituent groups on the benzene ring in the phenylethylamine derivatives and phenylacetic acid derivatives or amino acid derivatives.

[0027] (1) Synthesis of intermediate 4-alkoxyphenylacetic acid methyl ester (m1)

[0028] Weigh 0.009mol of methyl p-hydroxyphenylacetate and 0.009mol of anhydrous potassium carbonate, add them to...

Embodiment 2

[0076] Determination of α-amylase inhibitory activity of substituted tetrahydroisoquinoline derivatives.

[0077] The measuring instrument is a THERMO Varioskan Flash full-wavelength multifunctional microplate reader.

[0078] Measure the α-amylase inhibitory activity of the compound obtained by the method of Example 1 in the following way:

[0079] Experimental principle: The principle design of the color development between maltose produced by hydrolyzing starch with α-amylase and 3,5-dinitrosalicylic acid (DNS chromogen). Dinitrosalicylic acid (DNS chromogen) undergoes a redox reaction with reducing sugars to generate 3-amino-5-nitrosalicylic acid. The product is brownish red under boiling conditions, and the color is within a certain concentration range. The depth is proportional to the maltose content, and the maltose content is determined by colorimetry.

[0080] Solution preparation: pH 6.9 phosphate buffer solution; soluble starch dissolved in phosphate buffer as sub...

Embodiment 3

[0089] Determination of pancreatic lipase activity of substituted tetrahydroisoquinoline derivatives.

[0090] Measure pancreatic lipase activity with the compound that embodiment 1 method gains with the following method:

[0091] Experimental principle: Pancrelipase can hydrolyze 4-nitrophenyl palmitate (PNPP) to produce yellow 4-nitrophenol (PNP) and palmitic acid. PNP is yellow in aqueous solution, and its maximum absorption wavelength is 405nm, so Pancrelipase activity can be measured by calculating the change in PNP content by measuring the absorbance at 405 nm.

[0092] Solution preparation: the sample compound is first dissolved with a small amount of DMSO, and then diluted to the desired concentration with Tris-HCl buffer. Pancrelipase was made into 1.2 mg / mL enzyme solution with Tris-HCl buffer, and PNPP was first dissolved with a small amount of isopropanol, then diluted with Tris-HCl buffer to make 1 mmol / L substrate solution.

[0093] Each sample consists of 4 sy...

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Abstract

The invention belongs to the technical field of medicine. The invention relates to application of tetrahydro isoquinoline alkaloid which is shown in a formula (I) or a formula (II) or a pharmaceutically acceptable salt of the tetrahydro isoquinoline alkaloid in an aspect of preparing alpha-amylase inhibitors. Activity screening experiments prove that the compound disclosed by the invention has an effect of inhibiting activity of two kinds of in-vitro digestive enzyme of alpha-amylase and pancreatic lipase and inhibiting proliferation and differentiation activity of 3T3-L1 preadipocyte at the same time and has an application prospect in an aspect of clinical research on diabetes, hyperlipemia, obesity or metabolic syndrome.

Description

technical field [0001] The invention relates to the use of tetrahydroisoquinoline alkaloids in the preparation of in vitro digestive enzyme inhibitors such as α-amylase and 3T3-L1 preadipocyte proliferation and differentiation inhibitors. Background technique [0002] The World Health Organization has declared obesity the largest global adult chronic disease. The etiology of obesity is extremely complex, including the interaction of various behavioral, environmental, metabolic and genetic factors, and is generally caused by a long-term imbalance between energy intake and expenditure. Obesity not only affects the appearance, but also easily induces and increases the risk of cardiovascular and other metabolic diseases, including hypertension, hyperlipidemia, coronary artery disease and type 2 diabetes, etc., which has gradually become one of the world's health problems. [0003] Alpha-amylase is an endoglucosidase that acts on alpha-1,4-glucosidic bonds. The α-amylase in sal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/472A61P3/04A61P3/10A61P3/06A61P3/00G01N21/31G01N21/78
CPCA61K31/472G01N21/31G01N21/78
Inventor 蒋建勤李丹吕昊宇
Owner CHINA PHARM UNIV
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