2-phenyl-3-substituted-imidazo[1,2-a]pyridine derivatives and preparation method thereof

A pyridine derivative, 2-a technology, applied in the drug field of tumor and antiviral treatment, can solve the problem of low antitumor and virus inhibition rate

Active Publication Date: 2014-07-02
YANGTAI PHARMA SHANDONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some drugs can have a certain effect on anti-tumor and anti-virus, but the anti-tumor and anti-virus inhibition rate is not high

Method used

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  • 2-phenyl-3-substituted-imidazo[1,2-a]pyridine derivatives and preparation method thereof
  • 2-phenyl-3-substituted-imidazo[1,2-a]pyridine derivatives and preparation method thereof
  • 2-phenyl-3-substituted-imidazo[1,2-a]pyridine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1 7-methyl-2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde

[0080]

[0081] Under ice bath, slowly drop 1.38 mL (15 mmol) of phosphorus oxychloride into 10 mL of DMF, stir at room temperature for 1 h after the addition, and add 7-methyl-2-phenylimidazo[1,2 -a] DMF solution of pyridine (2.08g, 10 mmol), stirred at room temperature for 24h after the dropwise addition, poured into ice water, stirred for 1h, extracted three times with dichloromethane, combined the organic phases, washed with water, dried, and concentrated to obtain the crude product, The pure product was obtained by recrystallization from dichloromethane. Yield 86%. 1 H NMR (CDCl 3, TMS) δ(ppm): 2.5(s), 3H; 7.0(dd), 1H; 7.5-7.6(m), 4H; 7.8(m), 2H; 9.5(d), 1H; 1H..

Embodiment 2

[0083] Reference Example 1 prepared 7-methyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde with yield (89%). 1 H NMR (CDCl 3 , TMS) δ(ppm): 2.5(s), 3H; 7.3(d), 1H; 7.4(d), 2H; 7.8(s), 1H; 8.2(d), 2H; 9.4(d), 1H; 10.0(s), 1H. .

Embodiment 3

[0085] Reference Example 1 prepared 7-methyl-2-(4-bromophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde with yield (80%). 1 H NMR (CDCl 3 , TMS) δ(ppm): 2.5(s), 3H; 7.1(d), 1H; 7.6(s), 1H; 7.7(d), 2H; 7.8(d), 2H; 9.4(d), 1H; 10.0(s), 1H.

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Abstract

The present invention relates to 2-phenyl-3-substituted imidazo[1,2-a]pyridine derivatives, medicinal compound I for treating diseases such as tumors and viruses, its preparation method and application. Compared with the prior art, the present invention has the structure of formula I, and the anti-influenza virus effect is obviously improved, and it can also play a certain inhibitory effect on gastric adenocarcinoma cells, and discloses a pharmaceutically acceptable salt containing compound I And a pharmaceutical composition composed of one or several pharmaceutically acceptable carriers, excipients or diluents.

Description

1. Technical field [0001] The present invention relates to the field of drugs for tumor and antiviral treatment, more specifically, relates to a class of 2-phenyl-3-substituted imidazo[1,2-a]pyridine derivatives with antitumor or antiviral effects Its preparation method and application, and the pharmaceutical composition containing them. 2. Background technology [0002] In recent years, imidazo[1,2-a]pyridine compounds have attracted widespread attention. Such compounds have pharmacological activities such as prevention and treatment of gastric disease, anti-ulcer, anti-inflammation, anti-cancer, anti-virus, etc., for example: imidazo[1,2-a]pyridine described in patents CN87106804, CN200980148444.7, CN201010256861.8 The derivatives have pharmacological activity for preventing and treating gastrointestinal diseases; the 8-alkoxy substituted imidazo[1,2-a]pyridine involved in patents CN88106859.4 and CN87108027 has anti-ulcer activity; the patent number is The multi-substit...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00A61P31/12A61P31/16A61P1/00
Inventor曹晓群葛燕青顾建勇朱焰林晓辉
OwnerYANGTAI PHARMA SHANDONG