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Pentadienone-containing 4-substituted quinazoline derivative, preparation method and use thereof

A kind of technology of quinazoline and pentadienone, which is applied in the field of chemistry and achieves good inhibitory effect

Inactive Publication Date: 2011-10-19
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above literature studies have shown that both quinazoline compounds and 1,4-pentadien-3-one compounds have good anti-tumor effects, and there is no report of introducing 1,4-pentadien-3-one structure into Synthesis of compounds with dual active structures of 1,4-pentadien-3-one and quinazoline in quinazoline molecules

Method used

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  • Pentadienone-containing 4-substituted quinazoline derivative, preparation method and use thereof
  • Pentadienone-containing 4-substituted quinazoline derivative, preparation method and use thereof
  • Pentadienone-containing 4-substituted quinazoline derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of 1-(4-fluorophenyl)-5-(2-(quinazolin-4-oxyl) 1,4-pentadien-3-one:

[0034] (1) Synthesis of quinazolin-4-one:

[0035] Add 13.7g (0.1mol) 2-aminobenzoic acid and 20mL (4.2mol) formamide in the 250mL there-necked flask equipped with a thermometer and a condenser tube, keep the temperature between 135-145°C for reaction, during this process, the system From light gray turbid liquid to yellow-brown clear liquid, a small amount of light gray solid appeared on the wall of the reactor after 2 hours of reaction, and the reaction was complete after 4.5 hours. Formamide was decomposed, and a large amount of light gray solids were precipitated. Naturally cooled, suction filtered, and dried to obtain 14.52 g of the product, which was recrystallized with absolute ethanol to obtain 13.15 g of light gray flaky crystals, with a yield of 89.8%.

[0036] (2) Synthesis of 4-chloroquinazoline:

[0037] Add 11.00g (76mmol) of 4-quinazolinone, 80mL thionyl chloride,...

Embodiment 2

[0044] Example 2: Synthesis of 1-(3-nitrophenyl)-5-(2-(quinazolin-4-oxyl) 1,4-pentadien-3-one:

[0045] (1) Synthesis of quinazolin-4-one:

[0046] (2) Synthesis of 4-chloroquinazoline:

[0047] (3) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one:

[0048] (4) Synthesis of 4-(2-(quinazolin-4-oxyl)phenyl)-3-buten-2-one:

[0049] Above four steps are with embodiment 1 (1)-(4) step.

[0050] (5) Synthesis of 1-(3-nitrophenyl)-5-(2-(quinazolin-4-oxyl)1,4-pentadien-3-one:

[0051] Synthesize as in Example 1 (5) step method and conditions. The difference is that 3-nitrobenzaldehyde (0.5 mmol, 0.08 g) was added, reacted for 2 hours, melting point 189-191 o C, the yield is 46.3%.

Embodiment 3

[0052] Example 3: Synthesis of 1-(4-nitrophenyl)-5-(2-(quinazolin-4-oxyl) 1,4-pentadien-3-one:

[0053] (1) Synthesis of quinazolin-4-one:

[0054] (2) Synthesis of 4-chloroquinazoline:

[0055] (3) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one:

[0056] (4) Synthesis of 4-(2-(quinazolin-4-oxyl)phenyl)-3-buten-2-one:

[0057] Above four steps are with embodiment 1 (1)-(4) step.

[0058] (5) Synthesis of 1-(4-nitrophenyl)-5-(2-(quinazolin-4-oxyl)1,4-pentadien-3-one:

[0059] Synthesize as in Example 1 (5) step method and conditions. The difference is that 4-nitrobenzaldehyde (0.5 mmol, 0.08 g) was added, reacted for 2.5 h, melting point 200-202 o C, the yield is 48.4%.

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Abstract

The invention discloses a pentadienone-containing 4-substituted quinazoline derivative. A structure of the pentadienone-containing 4-substituted quinazoline derivative is represented as the following general formula (I), wherein a group shown in the specification is at a position 2 or a position 3 or a position 4 of a benzene ring; R1 is hydrogen, monosubstituted halogen atom or polysubstituted halogen atom, monosubstituted methyl or polysubstituted methyl, or polysubstituted methoxy; R2 is ortho, meta, para monosubstituted or polysubstituted nitrophenyl, ortho, meta, para monosubstituted or polysubstituted halogen atom phenyl, ortho, meta, para monosubstituted or polysubstituted methoxyphenyl, 2-chlorine-5-nitrophenyl, 4-chlorine-3-nitrophenyl, ortho, meta, para monosubstituted trifluoromethylphenyl, five-membered heterocyclic aryl or substituted five-membered heterocyclic aryl, or ortho, meta, para monosubstituted or polysubstituted hydroxyphenyl. The invention further discloses a preparation method for the pentadienone-containing 4-substituted quinazoline derivative and a use of the pentadienone-containing 4-substituted quinazoline derivative in preparing anti-cancer drugs.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to a pentadienone-containing 4-substituted quinazoline derivative, a preparation method of the derivative, and an application in cancer cell inhibitors. Background technique [0002] Quinazoline compounds have various biological activities such as anticancer, antiviral, and bactericidal, and have important applications in pesticide and pharmaceutical research. [0003] In terms of anti-cancer properties: In 2002, the quinazoline drug Erlotinib was approved by the US FDA as a second-line or third-line treatment drug for advanced NSCLC that failed standard treatment. The drug has shown a strong anti-tumor effect in preclinical studies, has high EGFR tyrosine kinase specificity, can selectively block human EGFR tyrosine kinase and reduce EGFR autophosphorylation, resulting in cell Growth stops and goes to apoptosis. It inhibits EGFR tyrosine kinase with an IC50 of 2 nmol·L-1; it a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/88C07D403/12C07D405/12A61K31/517A61P35/00A61P31/12
Inventor 宋宝安罗会杨涛
Owner GUIZHOU UNIV
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