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Pyrimidine derivatives containing 1,2,3-triazole and urea structural units, preparation method and use thereof
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A kind of structural unit, the technology of triazole, applied in the field of 4-substituted-5-cyano-6-aminopyrimidine derivatives
Active Publication Date: 2016-03-16
ZHENGZHOU UNIV
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However, there are few reports on the combination of pyrimidine compounds, urea active fragments and 1,2,3-triazole five-membered ring active fragments. Therefore, this study has very important value
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Embodiment 1
[0080] Example 1 general formula( II ), R 2 = Derivatives of 4-Isoproplphenyl ( II-1 ) preparation
[0081] Add ethyl cyanoacetate (2.3g, 20mmol) and sodiumhydroxide (1.2g, 30mmol) into the ethanol solution, and react for a period of time under reflux conditions, then add thiourea (2.3g, 30mmol) and p-isopropylBenzaldehyde (4.45g, 30mmol) was added into the reaction system, stirred and reacted, followed by TLC detection. After the reaction, filter with suction and recrystallize to obtain the pure product.
Embodiment 2
[0082] Example 2 general formula( III ), R 2 = Derivatives of 4-Isoproplphenyl ( III-1 ) preparation
[0083] Add propynebromide (3.6g, 30mmol) dropwise into a solution of II-1 (5.4g, 20mmol) in 1,4-dioxane, heat and stir to react. Monitor the reaction process with TLC until the reaction is complete; without separation, directly add phosphorus oxychloride (4.6g, 30mmol) dropwise to the reaction system. Filtration to obtain a solid, the pure compound III-1 solid was obtained by column chromatography. Yield64%, Yellowsolid. Mp: 131-132 o c. 1 HNMR (400MHz, CDCl 3,δ,ppm)δ8.20–8.07(m,2H,Ar-H),7.70–7.52(m,3H,Ar-H),4.01(d, J =2.6Hz,2H,-CH 2 -),2.28(t, J =2.6Hz,1H,≡C-H). 13 CNMR (100MHz, CDCl 3 ,δ,ppm):δ174.02,168.73,163.95,134.07,132.72,129.35,129.02,114.43,101.42,78.17,71.63,20.36.HR-MS(ESI):Calcd.C 14 h 9 ClN 3 S,[M+H] + m / z:286.0206,found:286.0202.
Embodiment 3
[0084] Example 3 general formula( IV ), the preparation of general formula IV
[0085] Disperse chloroacetamide (0.94g, 10mmol) in acetonesolvent, add oxalyl chloride (1.9g, 15mmol) dropwise while stirring at room temperature, transfer the whole system to an oil bath and heat at 90°C for 4h, then cool to room temperature , o-aminopyridine (1.4g, 15mmol) was added dropwise, stirred, a solid was precipitated, filtered by suction to obtain a solid, and the general formula IV was obtained after separation and purification. Yield 80%.
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Abstract
The invention belongs to the field of medicinal chemistry and discloses 4-substituted-5-cyano-6-aminopyrimidine derivatives with antitumor activity of 1,2,3-triazole and urea structural units, their synthesis method and application . The present invention uses a three-component one-pot method to construct pyrimidine active fragments, and then prepares a series of 4-substituted 1,2,3-triazole and urea structural units through reactions such as cyclization, substitution, chlorination and ammonolysis. -5-cyano-6-aminopyrimidine derivatives. The general formula of the compound of the present invention is shown in I. In vitro anti-tumor activity experiments have proved that this type of compound has obvious inhibitory and killing effects on a variety of tumor cells, and further optimization of this is expected to obtain a class of new anti-tumor drugs.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry and discloses 4-substituted-5-cyano-6-aminopyrimidine derivatives with antitumor activity containing 1,2,3-triazole and urea structural units, their preparation methods and Its application as a new class of antitumor druglead compound. Background technique [0002] Tumor is a disease that seriously endangers human health and is difficult to overcome. There are many anti-tumor drugs that have been marketed, but there are still some problems in these drugs, such as high toxicity, weak targeting, and easy drug resistance. Therefore, the research and development of new anticancer drugs is particularly important. [0003] 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 compo...
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