Unlock instant, AI-driven research and patent intelligence for your innovation.

Derivatives of dihydroaurone, benzofuran and orange alkane, and uses thereof

A technology of derivatives and neranes, applied in the field of pharmaceutical applications, can solve problems such as insufficient activity, complex synthesis, and high toxicity

Inactive Publication Date: 2015-01-14
SHENYANG PHARMA UNIVERSITY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been a lot of reports on the design and synthesis of new anti-tumor active compounds using CA-4 as the lead compound, but most CA-4 analogs have shortcomings such as insufficient activity, high toxicity, or relatively complicated synthesis.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Derivatives of dihydroaurone, benzofuran and orange alkane, and uses thereof
  • Derivatives of dihydroaurone, benzofuran and orange alkane, and uses thereof
  • Derivatives of dihydroaurone, benzofuran and orange alkane, and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Example 1 Preparation of 6,7-dimethoxy-(4-methoxybenzyl)benzofuran-3(2H)-one (compound 1-01)

[0104] Dissolve 6,7-dimethoxy-(4-methoxybenzylidene)benzofuran-3(2H)-one (1.0g, 3.20mmol) in ethyl acetate, add 0.2g 10% Palladium carbon, stirred at room temperature for about 2 hours under a hydrogen atmosphere, after the reaction was completed, filtered, and the filtrate was distilled off the solvent under reduced pressure to obtain a crude product, which was separated by column chromatography to obtain 1-01 with a yield of 93%.

[0105] The structural formula of compound 1-01, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 2

[0106] Example 2 Preparation of 2-(4-hydroxybenzyl)-6,7-dimethoxybenzofuran-3(2H)-one (compound 1-02)

[0107] Compound 1-02 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 87%.

[0108] The structural formula of compound 1-02, 1 H-NMR and MS data are listed in Table-1 below.

Embodiment 3

[0109] Example 3 Preparation of 2-(3-hydroxy-4-methoxybenzyl)-6,7-dimethoxybenzofuran-3(2H)-one (compound 1-03)

[0110] Compound 1-03 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 85%.

[0111] The structural formula of compound 1-03, 1 H-NMR and MS data are listed in Table-1 below.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of pharmaceutical, and relates to derivatives of dihydroaurone, benzofuran, and orange alkane. The structures of the derivatives are as shown in formula (1): wherein, when Xl and X2 together represent oxygen, and -Y-Z- is -C-CH-, the structures are dihydroaurone compounds; when Xl and X2 together represent hydrogen, and -Y-Z- is -C=C-, the structures are benzofuran compounds; or when Xl and X2 simultaneously and respectively represent hydrogen, and -Y-Z- is -C-CH-, the structures are orange alkane compounds. The invention also provides pharmaceutically acceptable non-toxic salts and hydrates formed from the derivatives shown in the structural formula. The pharmaceutically acceptable non-toxic salts include the salts formed by the derivatives and acids. Pharmacological activity test results show that the derivatives have good antitumor activities and can be used as a tumor cell proliferation inhibitor in the preparation of tumor pharmaceuticals.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a kind of dihydroorangeones, benzofurans, and tangerane derivatives and their uses. pharmaceutical applications. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is the leading cause of death in China. Searching for and discovering new drugs for the treatment and prevention of tumors is a major issue at present. [0003] Combretastatin A-4 (CA-4) is a cis-stilbene natural product isolated from South African dwarf willow, and its chemical name is ( Z )-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol. CA-4 is an inhibitor of tubulin polymerization, which exhibits strong anti-tumor cell proliferation activity. Its prodrug CA-4 phosphate (CA-4P) has entered the phase III clinical research stage in the United States. There have been many reports on the design and synthesis of new anti-tumor active compounds using CA-4 as the...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/86C07D493/04A61K31/343A61K31/36A61P35/00
Inventor 张为革江建华吴英良沈杞容乔拂晓孙俊
Owner SHENYANG PHARMA UNIVERSITY