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Quinazoline-containing thioether substituted pentadiene ketone derivatives, and preparation method and application thereof

A kind of technology of pentadienone and oxazoline sulfide, which is used in pentadienone derivatives substituted with quinazoline sulfide and the fields of preparation and use

Active Publication Date: 2015-05-13
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no reports of quinazoline thioether-substituted pentadienone compounds with anti-plant virus activity

Method used

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  • Quinazoline-containing thioether substituted pentadiene ketone derivatives, and preparation method and application thereof
  • Quinazoline-containing thioether substituted pentadiene ketone derivatives, and preparation method and application thereof
  • Quinazoline-containing thioether substituted pentadiene ketone derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Compound (1E,4E) 1-(2-thienyl)-5-(4-(2-((quinazoline)-4-thio)ethoxy)phenyl)-1,4 - Pentadien-3-one:

[0040] (1) quinazoline-4-(3 H )-ketone synthesis

[0041] Add anthranilic acid (0.2 mol) and formamide (0.8 mol) into a 250 mL three-neck flask equipped with a thermometer and a condenser tube to keep the temperature at 135-150 °C for reaction. During this process, the system changes from light gray turbid liquid to Yellowish-brown clear liquid, TLC tracking reaction (developer: petroleum ether: ethyl acetate = 1:1, V / V), the reaction is complete in about 5 hours, after natural cooling to 100°C, slowly add 1.0 times the volume of water to the system, Decompose the excess formamide, and at the same time, a light gray solid precipitates out. After natural cooling, transfer it to a large beaker, and then add 1.5 times the volume of water, and the off-white solid still precipitates. Filter it with suction and recrystallize it with absolute ethanol to obtain a ...

Embodiment 2

[0054] Example 2: Compound (1E, 4E) 1-(2-thienyl)-5-(4-(2-((8-methylquinazoline)-4-thio)ethoxy)phenyl) Synthesis of -1,4-pentadien-3-one:

[0055] (1) Intermediate 8-methylquinazoline-4-(3 H )-ketone preparation: the synthesis steps and process conditions are the same as in Example 1 (1), the difference is that 8-methylanthranilic acid is a raw material;

[0056] (2) Preparation of intermediate 8-methyl-4-chloroquinazoline: the synthesis steps and process conditions are the same as in Example 1 (2), the difference is that 8-quinazoline-4-(3 H )-ketone is a raw material;

[0057] (3) Preparation of intermediate quinazoline-4-thiol: the synthesis steps and process conditions are the same as in Example 1 (3), the difference is that 8-methyl-4-chloroquinazoline is used as the raw material;

[0058] (4) Preparation of intermediate (1E) 4-(4-hydroxyphenyl)-3-buten-2-one: the synthesis steps and process conditions are the same as in Example 1 (4);

[0059] (5) Preparation of inte...

Embodiment 3

[0062] Example 3: Compound (1E,4E) 1-(2-furyl)-5-(4-(2-((quinazoline)-4-thio)ethoxy)phenyl)-1,4 -Synthesis of pentadien-3-one:

[0063] (1) Intermediate quinazoline-4-(3 H )-ketone preparation: synthetic steps and process conditions are the same as embodiment one (1);

[0064] (2) Preparation of intermediate 4-chloroquinazoline: the synthesis steps and process conditions are the same as in Example 1 (2);

[0065] (3) Preparation of the intermediate quinazoline-4-thiol: the synthesis steps and process conditions are the same as in Example 1 (3);

[0066] (4) Preparation of intermediate (1E) 4-(4-hydroxyphenyl)-3-buten-2-one: the synthesis steps and process conditions are the same as in Example 1 (4);

[0067] (5) Preparation of intermediate 1-(4-hydroxyphenyl)-5-(2-furyl)-1,4-pentadien-3-one: the synthesis steps and process conditions are the same as in Example 1 (5 ), the difference is that furfural is a raw material;

[0068] (6) Preparation of intermediate 1-(4-(2-bromo...

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Abstract

The invention discloses a preparation method and bioactivity of new compounds for preventing and treating plant virus diseases (quinazoline-containing thioether substituted pentadiene ketone compounds), particularly compounds disclosed as the following general formula (I) and a preparation method thereof. The quinazoline-containing thioether substituted pentadiene ketone compounds are prepared from ortho-aminobenzoic acid, formamide, thionyl chloride, thiocarbamide, 4-hydroxybenzaldehyde, acetone, substituted aromatic aldehyde, substituted heterocyclic aldehyde and 1,2-ethylene dibromide by seven reaction steps by using 1,2-dichloroethane, ethanol and N,N-dimethylformamide as solvents and NaOH, K2CO3 and KOH as catalysts. The compounds K01, K02, K03, K04, K05, K06, K07, K09, K10, K12, K13, K15, K16, K17, K18, K19, K20, K21, K23 and K27 have favorable anti-plant virus activity (I).

Description

technical field [0001] The present invention relates to quinazoline sulfide-substituted pentadienone derivatives with anti-plant virus effect, preparation method thereof, preparation method of the compound and anti-tobacco mosaic virus disease, cucumber mosaic virus disease, southern rice Black-streaked dwarf virus disease and rice stripe leaf blight virus have inhibitory uses. Background technique [0002] Plant virus disease is called "plant cancer", which has brought extremely serious harm to agricultural production. Due to the extremely complex mechanism of its occurrence, infection and transmission, it is a major problem in current prevention and control research. In order to prevent and treat plant virus diseases, people conduct research from various channels such as natural product extraction and artificial synthesis, and more and more new plant virus inhibitors have been screened and developed, such as Ningnanmycin, ribavirin and amino oligosaccharides, etc. , but ...

Claims

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Application Information

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IPC IPC(8): C07D239/93A01P1/00
CPCC07D239/93
Inventor 胡德禹龙承文宋宝安薛伟李向阳陈美航董良润甘秀海
Owner GUIZHOU UNIV
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