4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound as well as preparation method and application of 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound

A trialkoxyquinazoline and compound technology, which is applied in the field of preparation of 4--5,6,7-trialkoxyquinazoline compounds, can solve the problems of anti-phytopathogenic fungi and low anti-cancer activity and the like

Active Publication Date: 2013-02-27
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] It can be seen from the background technology that quinazoline (ketone) compounds have good biological activities such as anti-plant bacteria, anti-plant virus, anti-cancer, etc., but about 4-(4-substituted piperazine)-5,6,7 - Trialkoxyquinazoline compounds have not been synthesized at present, and there are relatively few research reports on the anti-phytopathogenic fungi and anti-cancer activities of these compounds at home and abroad

Method used

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  • 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound as well as preparation method and application of 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound
  • 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound as well as preparation method and application of 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound
  • 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound as well as preparation method and application of 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1, 5,6,7-trimethoxy-4-(4-(2-(trifluoromethyl)benzenesulfonyl)piperazine)quinazoline

[0105] (Compound number is a ) Synthesis

[0106] (1) Synthesis of 2,3,4-trimethoxybenzoic acid

[0107] Stir 5.0 g of 2,3,4-trihydroxybenzoic acid and 20 mL of water in a bottle, and add 25 mL of sodium hydroxide solution (4mol / L) and 20 g of dimethyl sulfate dropwise in a water bath at room temperature. After the dropwise addition, heat to reflux for 6 h, stop the reaction, use hydrochloric acid to adjust the PH value to neutral, a brown solid precipitates out, filter and dry the crude product to obtain the crude product, extract the filtrate with chloroform to obtain the crude product, combine the crude product with column layer The target compound was separated and purified by analysis to obtain 4.2 g of a white solid with a yield of 67.3%.

[0108] (2) Synthesis of methyl 2,3,4-trimethoxybenzoate

[0109] Mix and stir 1.2 g of 2,3,4-trimethoxybenzoic acid and 5 mL of m...

Embodiment 2

[0124] Example 2. Compound 5,6,7-trimethoxy-4-(4-(4-methylbenzenesulfonyl)piperazine)quinazoline

[0125] (Compound number is c )Synthesis

[0126] (1) Synthesis of 2,3,4-trimethoxybenzoic acid

[0127] Synthesize as embodiment one (1) condition and method

[0128] (2) Synthesis of methyl 2,3,4-trimethoxybenzoate

[0129] Synthesize as embodiment one (2) condition and method

[0130] (3) Synthesis of methyl 6-nitro-2,3,4-trimethoxybenzoate

[0131] Synthesize as embodiment one (3) condition and method

[0132] (4) Synthesis of methyl 6-amino-2,3,4-trimethoxybenzoate

[0133] Synthesize as embodiment one (4) condition and method

[0134] (5) 5,6,7-trimethoxyquinazoline-4-(3H )-ketone synthesis

[0135] Synthesize as embodiment one (5) condition and method

[0136] (6) Synthesis of 4-chloro-5,6,7-trimethoxyquinazoline

[0137] Synthesize as embodiment one (6) condition and method

[0138] (7) Synthesis of 4-(N-Boc-piperazine)-5,6,7-trimethoxyquinazoline

[0139] Syn...

Embodiment 3

[0144] Embodiment three, compound 5,6,7-trimethoxy-4-(4-(4-methoxybenzenesulfonyl) piperazine) quinazoline (the compound number is d )Synthesis

[0145] (1) Synthesis of 2,3,4-trimethoxybenzoic acid

[0146] Synthesize as embodiment one (1) condition and method

[0147] (2) Synthesis of methyl 2,3,4-trimethoxybenzoate

[0148] Synthesize as embodiment one (2) condition and method

[0149] (3) Synthesis of methyl 6-nitro-2,3,4-trimethoxybenzoate

[0150] Synthesize as embodiment one (3) condition and method

[0151] (4) Synthesis of methyl 6-amino-2,3,4-trimethoxybenzoate

[0152] Synthesize as embodiment one (4) condition and method

[0153] (5) 5,6,7-trimethoxyquinazoline-4-( 3H )-ketone synthesis

[0154] Synthesize as embodiment one (5) condition and method

[0155] (6) Synthesis of 4-chloro-5,6,7-trimethoxyquinazoline

[0156] Synthesize as embodiment one (6) condition and method

[0157] (7) Synthesis of 4-(N-Boc-piperazine)-5,6,7-trimethoxyquinazoline

[015...

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Abstract

The invention discloses a 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound as well as a preparation method and application of the 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compound, wherein the compound structure is shown as the following general formula (I). A series of novel 4-(4-substituted piperazine)-5,6,7-trialkoxy quinazoline type compounds are synthesized by using 2,3,4-trihydroxy benzoic acid, dimethyl sulfate, diethyl sulfate, methanol, sulfuric acid, nitric acid, hydrogen gas, formamide, phosphorus oxychloride, N-Boc piperazine, hydrochloric acid, aryl sulfonyl chloride and 4-aromatic (benzyl, pyridine and morpholine propyl) substituted piperazine as raw materials through multiple steps. The compound has a better anticancer effect and a plant fungus inhibition effect and can be used for preparing anticancer medicine and plant fungus resistance pesticide. (I) is shown as the accompanying drawing.

Description

Technical field [0001] The present invention involves 4- (4-replacement of thiazide) -5,6,7-triaxoolooline preparation method and application of anti-cancer effects and antibiotic bacteria. Background technique [0002] Pootholin compounds show good biological activity and become one of the hot spots for scholars in chemical and biology.In terms of pesticides, biological activity such as antibacterial, antiviral, and mites of antibacterial, antiviral, and mites.Among them, El-436 (EL-436) is a simple and high-efficiency new type of mite killing agent launched by the US DOW-Lanco Corporation (Tao's Agricultural Company) in the late 1980s.In terms of medicine, since the discovery of FRY et al. In 1994, 4-aniline cepatoline (PD 153035) as a specific inhibitor of EGFR tyrosine kinases, azozolin compounds have become one of the hot spots for the development of anticancer drugs.Develop many commercialized drugs.For example, Gefitinib ZD1839 (IRSSA) and Elotinib OSI-774 (Tarceva) have a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94C07D401/12A01P3/00A61P35/00
Inventor 杨松张英薛伟向红梅王培义胡德禹张秋云金林红尹娟冉义江
Owner GUIZHOU UNIV
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