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5h-quinazoline[3,2-b]cinnoline-7,13-dione compound and preparation method thereof

A compound, 2-b technology, applied in the fields of organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problems of restricting the development of the field, and achieve the effect of anti-tumor activity and a wide range of substrate applications

Active Publication Date: 2018-09-18
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although people have systematically studied the synthesis and biological activity of quinazolinone tetracyclic compounds and achieved fruitful research results, most of the existing research methods focus on the structure of the known quinazolinone tetracyclic skeleton. In terms of modification and transformation, this restricts the development of this field to a certain extent

Method used

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  • 5h-quinazoline[3,2-b]cinnoline-7,13-dione compound and preparation method thereof
  • 5h-quinazoline[3,2-b]cinnoline-7,13-dione compound and preparation method thereof
  • 5h-quinazoline[3,2-b]cinnoline-7,13-dione compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0013]

[0014] Add o-bromoacetophenone 1a (119mg, 0.6mmol), dimethyl sulfoxide (3mL) and iodine (152mg, 0.6mmol) sequentially into a 25mL reaction flask, heat and stir at 110°C for 3h, then cool to At room temperature, 2-aminobenzoic hydrazide 2a (90.8mg, 0.4mmol) and K 2 CO 3 (221mg, 1.6mmol), stirred at room temperature for 5h, then heated and stirred at 100°C for 6h. After the reaction was completed, a saturated ammonium chloride solution was added to the reaction flask to quench the reaction, extracted with dichloromethane, the organic phase was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=2 / 1, v / v), and obtained yellow solid 5-phenyl-5H-quinazoline[3,2-b]cinnoline- 7,13-Diketone 3a (106 mg, 78%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,600MHz)δ7.29(t,J=7.2Hz,1H),7.33(t,J=7.2Hz,1H),7.37-7.41...

Embodiment 2

[0016] According to the method described in Example 1, o-bromoacetophenone 1a (79.6mg, 0.4mmol), dimethyl sulfoxide (3mL) and iodine element (102mg, 0.4mmol) were added successively in a 25mL reaction flask. Heat and stir at 110°C for 3h, then cool to room temperature, add 2-aminobenzoic hydrazide 2a (90.8mg, 0.4mmol) and K 2 CO 3 (166mg, 1.2mmol), stirred at room temperature for 5h, then heated and stirred at 100°C for 6h to obtain the product 5-phenyl-5H-quinazoline[3,2-b]cinnoline-7,13-di Ketone 3a (92 mg, 68%).

Embodiment 3

[0018] According to the method described in Example 1, o-bromoacetophenone 1a (79.6mg, 0.4mmol), dimethyl sulfoxide (3mL) and iodine (20.3mg, 0.08mmol) were added successively in a 25mL reaction flask, Heat and stir the reaction at 110°C for 3h, then cool to room temperature, add 2-aminobenzoic hydrazide 2a (90.8mg, 0.4mmol) and K 2 CO 3 (166mg, 1.2mmol), stirred at room temperature for 5h, then heated and stirred at 100°C for 6h to obtain the product 5-phenyl-5H-quinazoline[3,2-b]cinnoline-7,13-di Ketone 3a (33 mg, 24%).

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Abstract

The invention discloses a 5H-quinazoline[3, 2-b] cinnoline-7,13-diketone compound and a preparation method thereof, and belongs to the technical field of synthesis of novel quinazolinone tetracyclic compounds. The technical scheme has the key points that the structure of the 5H-quinazoline[3, 2-b] cinnoline-7, 13-diketone compound is described in the description. The invention also discloses the preparation method of the 5H-quinazoline[3, 2-b] cinnoline-7,13-diketone compound. In a preparation process, starting materials are cheap and available, and the application range of a primer is wide; and in a reaction process, use of a transition metal catalyst is prevented, so that the synthesized 5H-quinazoline[3, 2-b] cinnoline-7,13-diketone compound has potential antitumor activity.

Description

technical field [0001] The invention belongs to the technical field of synthesis of novel quinazolinone tetracyclic compounds, and in particular relates to a 5H-quinazolin[3,2-b]cinnoline-7,13-dione compound and a preparation method thereof. Background technique [0002] As an important nitrogen-containing heterocyclic compound, tetracyclic compounds containing quinazolinone structural units not only widely exist in natural alkaloids with important physiological activities, but also exhibit powerful antibacterial, anticancer, UV-A The activity of protecting and scavenging DPPH free radicals has attracted more and more attention and research of organic and medicinal chemists in recent years. Although people have systematically studied the synthesis and biological activity of quinazolinone tetracyclic compounds and achieved fruitful research results, most of the existing research methods focus on the structure of the known quinazolinone tetracyclic skeleton. In terms of modif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D495/14A61P35/00
CPCC07D487/04C07D495/14
Inventor 郭胜海王芳翟剑辉范学森
Owner HENAN NORMAL UNIV
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