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1-Aromatic aldoxime uracil and its preparation method

A technology of oxime uracil and aromatic aldoxime, which is applied in the field of 1-aryl aldoxime uracil and its preparation, can solve problems such as toxicity and drug resistance, achieve high feasibility, inhibit thymidine phosphorylase and anti-tumor activity , the effect of reducing production costs

Inactive Publication Date: 2020-04-21
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, long-term clinical use of the same TP inhibitor may have side effects such as toxicity and drug resistance

Method used

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  • 1-Aromatic aldoxime uracil and its preparation method
  • 1-Aromatic aldoxime uracil and its preparation method
  • 1-Aromatic aldoxime uracil and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: A kind of 1-aromatic aldoxime uracil has the following structure I:

[0023]

[0024] Wherein, R1 is methyl or hydrogen, R2 is chlorine, iodine, carboxyl or hydrogen, Ar is alkylphenyl, halogenated phenyl, alkoxyphenyl, thienyl, furyl.

[0025] The 1-aromatic aldoxime uracil has a structural formula:

[0026]

[0027] The preparation method of 1-aromatic aldoxime uracil, its synthetic reaction formula is:

[0028]

[0029] R 1 =CH 3 , H R 2 = Cl, I, COOH, H

[0030] Concrete preparation steps are as follows:

[0031] (1) Dissolve 0.02mol of aromatic aldehyde in 25mL of methanol and stir at room temperature. After the aromatic aldehyde is completely dissolved, add 0.02mol of hydroxylamine hydrochloride and 0.022mol of potassium carbonate into methanol and react for 3 hours. After the reaction is complete, extract the reaction solution. Then wash with saturated sodium bicarbonate solution, dry with anhydrous sodium sulfate, and recover metha...

Embodiment 2

[0044] Embodiment 2: a kind of 1-aromatic aldoxime uracil, its structural formula is

[0045]

[0046] (Z)-1-((2-fluorophenyl)(oximino)methyl)-6-methylpyrimidine-2,4-(1H,3H)-dione (Compound 2).

[0047] White solid; M.p.248-249°C; IR(KBr,ν max ,cm -1 ):3440,2919,1695,1432,1302,1179,989,811,512; 1 H NMR (600MHz, DMSO-d 6 )(δ,ppm):12.57(s,1H,NH),11.50(s,1H,OH),7.52-7.47(m,J=7.6Hz,3H,ArH),7.46-7.33(m,1H,ArH ),5.73(s,1H,CH),1.89(s,3H,CH 3 ); 13 CNMR (150MHz, DMSO-d 6 )(δ,ppm):163.4,162.1,152.3,149.8,142.5(d, 3 J C–F =3Hz), 134.6(d, 3 J C–F =7.5Hz), 131.7(d, 3 J C–F =7.5Hz), 121.7(d, 3 J C–F =1.5Hz), 117.6(d, 2 J C–F =21Hz), 112.3(d, 2 J C–F =24Hz), 101.8, 18.3; HRMS (ESI-TOF, [M+H] + ): m / z calcd for C 12 h 10 FN 3 o 3 , 264.0779; found, 264.0776.

Embodiment 3

[0048] Embodiment 3: a kind of 1-aromatic aldoxime uracil, its structural formula is

[0049]

[0050] (Z)-1-((4-fluorophenyl)(oximino)methyl)-6-methylpyrimidine-2,4-(1H,3H)-dione (compound 3).

[0051] White solid; M.p.234-235℃; IR(KBr,νmax,cm-1):3419,2921,1706,1513,1459,1159,841,605,538;1H NMR(500MHz,DMSO-d6)(δ,ppm):12.36 (s,1H,NH),11.48(s,1H,OH),7.70-7.67(m,J=8.5Hz,2H,ArH),7.31-7.28((m,J=7Hz,2H,ArH),5.72 (s,1H,CH),1.89(s,3H,CH3); 13 C NMR (125MHz, DMSO-d 6 )(δ,ppm):163.4,162.7,152.4,149.8,142.5,128.7(d, 3 J C–F =2.5Hz), 128.0(d, 3 J C–F =8.8Hz), 116.7, 116.5, 101.6, 18.3; HRMS (ESI-TOF, [M+H] + ): m / z calcd for C 12 h 10 FN 3 o 3 , 264.0779; found, 264.0776.

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Abstract

1-aromatic aldoxime uracil and a preparation method of same. The invention relates to the field of medicines and particularly provides 1-aromatic aldoxime uracil, which can inhibit growth activity of tumor cells and significantly inhibit thymidine phosphorylase and has antitumor activity, as well as a preparation method of same. The 1-aromatic aldoxime uracil is represented by the structure (I), wherein R1 is a methyl group or hydrogen, R2 is chlorine, iodine, a carboxyl group or hydrogen, Ar is an alkyl phenyl group, halogenated phenyl group, an alkoxyphenyl group, a thienyl group or a furyl group. The 1-aryl aldoxime uracil has high activity of inhibiting growth of tumor cells, has significant inhibition effect on thymidine phosphorylase and has antitumor activity. The method has simple processes and high availability, has convenience in large-scale production and can reduce production cost.

Description

technical field [0001] The invention relates to the field of medicines, in particular to a 1-aromatic aldoxime uracil which inhibits tumor cell growth, has significant thymidine phosphorylase inhibitory and antitumor activities, and a preparation method thereof. Background technique [0002] Angiogenesis plays an important role in the process of tumor growth and metastasis. Thymidine phosphorylase (TP), an enzyme involved in thymidine homeostasis and metabolism, is thought to be angiogenesis-dependent due to its tropometric movement of endothelial cells that stimulates endothelial cell migration. The main function of this enzyme is to reversibly phosphorylate thymidine to thymine and 2-deoxyribose-1-phosphate, and to activate 5-fluorouracil and its precursors. Thymidine phosphorylase can recognize not only thymidine but also deoxyuridine and pyrimidine nucleoside derivatives. Based on gene sequence comparison, human thymidine phosphorylase is equivalent to angiogenic prote...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/54C07D239/553C07D239/557C07D409/06A61P35/00
CPCC07D239/54C07D239/553C07D239/557C07D409/06
Inventor 金毅林军赵舒悦蒋昆明
Owner YUNNAN UNIV
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