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2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, preparation method and application thereof

A compound, triazole technology, applied in the application field of anti-tumor drug lead compound

Active Publication Date: 2016-03-30
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the combination of the two, so this study has very important value

Method used

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  • 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, preparation method and application thereof
  • 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, preparation method and application thereof
  • 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, preparation method and application thereof

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Experimental program
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preparation example Construction

[0059] The preparation of general formula (II) is obtained with reference to the following documents:

[0060] H.I. Skulnick, J.H. Ludens, M.G. Wendling. Journal of Medicinal Chemistry, 1986, 29, 1499-1504.

[0061] The preparation of general formula (IV) is obtained with reference to the following documents:

[0062] (a) Ina Wilkening.; Giuseppedel Signore.; C.P.R. Hackenberger. Chem. Commun. 2011, 47, 349-351. (b) Mingyu Hu.;

Embodiment 1

[0063] Shown in embodiment 1 general formula (II), R 3 =H''s derivative (II-1) preparation

[0064] Add ethyl cyanoacetate (2.262g, 20mmol) and sodium hydroxide (1.200g, 30mmol) into the ethanol solution, under reflux, react for a period of time, then add thiourea (2.284g, 30mmol) and benzaldehyde (3.184 g, 30mmol) was added to the reaction system, the reaction was stirred, followed by TLC detection. After the reaction, filter with suction and recrystallize to obtain the pure product.

Embodiment 2

[0065] Shown in embodiment 2 general formula (III), R 3 =H''s derivative (III-1) preparation

[0066] Add propyne bromide (3.569g, 30mmol) dropwise into a solution of II-1 (2.674g, 10mmol) in 1,4-dioxane, and heat and stir to react. Monitor the reaction process with TLC until the reaction is complete; then directly dropwise add phosphorus oxychloride (4.600g, 30mmol) to the reaction system, after the reaction is complete, pour it into ice water, stir, and solids are precipitated, filtered by suction to obtain Solid, the solid of pure compound III-1 was obtained by column chromatography. Yield 64%, pale yellow solid. 1 HNMR(400MHz, CDCl3,δ,ppm)δ8.18–8.05(m,2H,Ar-H),7.71–7.50(m,3H,Ar-H),4.01(d,J=2.6Hz,2H,- CH2-),2.28(t,J=2.6Hz,1H,≡C-H).13CNMR(101MHz,CDCl3)δ174.02,168.73,163.95,134.07,132.72,129.35,129.02,114.43,101.42,78.17,71.63,20.36.

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Abstract

The invention discloses 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, a preparation method and application thereof in preparation of medicine and belongs to the field of medicinal chemistry. A pyrimidine parent nucleus and a 1,2,3-triazole activity unit are combined by using classical click chemistry to simply and efficiently synthesize the 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole in an environment-friendly manner. The 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole have a structure general formula as shown in the specification. In vitro anticancer activity tests show that the compounds have a certain inhibition effect on many tumor cells including EC-109, MCF-7, MGC-803 and B16 and can be applied to preparation of an antitumor medicine, as a further developed candidate or lead compound.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel 2,4,6-trisubstituted pyrimidine compounds containing 1,2,3-triazole, their preparation method and their use as a class of new antitumor drugs Application of lead compounds. Background technique [0002] Click chemistry, first proposed by the American chemist Sharpless, who won the Nobel Prize in Chemistry in 2001, currently refers to a class of Cu(I)-catalyzed reactions between azide compounds and alkyne compounds to generate 1,2,3-triazoles Reactions of five-membered ring compounds. Due to its mild reaction conditions, high reaction yield, simple post-treatment of products and many other advantages, it has been widely used in the optimization of drug lead compounds and the construction of compound libraries. 1,2,3-Triazoles exhibit a variety of biological activities, such as anti-inflammatory, anti-allergic, anti-tuberculosis, antibacterial, and anti-HIV act...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12A61K31/506A61P35/00
CPCC07D403/12
Inventor 刘宏民马立英庞露苹王博张淼户彪郑甲信张恩
Owner ZHENGZHOU UNIV
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