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Pyrimidine dehydroabietate derivatives and preparation method and application thereof

A technology of hydroabietic acid pyrimidine and dehydroabietic acid, which is applied in the field of medicine, can solve the problems that there are no public reports of dehydroabietic acid pyrimidine derivatives, and achieve the effects of improving antitumor activity, stable quality, and simple operation

Inactive Publication Date: 2020-06-09
GUILIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although it has been reported in the existing literature that many structural modifications have been carried out on the dehydroabietic acid core to obtain a series of dehydroabietic acid derivatives, there is no dehydroabietic acid and pyrimidine splicing to obtain dehydroabietic acid pyrimidine derivatives. public reports of

Method used

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  • Pyrimidine dehydroabietate derivatives and preparation method and application thereof
  • Pyrimidine dehydroabietate derivatives and preparation method and application thereof
  • Pyrimidine dehydroabietate derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of bromoethyl dehydroabietate 2:

[0040] Dissolve 6.00g (20mmol) of dehydroabietic acid in 100ml of acetone, heat in a water bath, then add 5.52g (40mmol) of anhydrous potassium carbonate, and slowly add 5.2ml (60mmol) of dibromoethane dropwise, and react at a constant temperature of 60°C. TLC followed the progress of the reaction. After the reaction is complete, filter, distill and concentrate at 50°C to obtain a yellow oily liquid, purify by column chromatography, distill and concentrate, and vacuum dry to obtain a transparent oily liquid, which is cooled and condensed into 6.2 g of a white solid, with a yield of 78.6%; m.p.46.2 -49.4°C;

[0041] Therefore, above-mentioned compound 2 is bromoethyl dehydroabietate, and its structural formula is as shown in the following formula:

[0042]

Embodiment 2

[0044] Preparation of 2'-(4-hydroxypyrimidin-2-yl)mercapto dehydroabietic acid ethyl ester 4a:

[0045] Dissolve 3mmol of pyrimidine compound 3a (4-hydroxy-2-mercaptopyrimidine), 3mmol (1.22g) of bromoethyl dehydroabietate in 20ml of DMF, then add 3mmol of anhydrous potassium carbonate, and react for 8-10 hours under stirring at room temperature , the progress of the reaction was monitored by TLC. After the reaction is complete, the reactant is poured into 100ml of ice water, and acidified with glacial acetic acid until no precipitation occurs; the precipitate is filtered, washed with water, dried and purified to obtain a light yellow solid with a yield of 56.1%, m.p.82.2~84.7°C ;

[0046] 1 H NMR (600MHz, CDCl 3 )δ7.81(d, J=6.6Hz, 1H), 7.28(s, 1H), 7.18(d, J=8.2Hz, 1H, H-11), 7.02(d, J=8.1Hz, 1H, H -12),6.90(s,1H,H-14),6.21(d,J=6.5Hz,1H),4.34(dd,J=31.8,8.7Hz,2H),3.45(d,J=15.9Hz, 2H),2.90(s,1H),2.84(s,1H),2.31(d,J=11.4Hz,1H),2.24(d,J=12.5Hz,1H),2.06(s,1H),1.83( d,J=5.4Hz...

Embodiment 3

[0050] Preparation of 2'-(4-hydroxyl-6-propylpyrimidin-2-yl)mercapto dehydroabietic acid ethyl ester (compound 4b):

[0051] Dissolve 3mmol of pyrimidine compound 3b (4-hydroxy-2-mercapto-6-propylpyrimidine) and 3mmol of bromoethyl dehydroabietate in 20ml of DMF, then add 3mmol of anhydrous potassium carbonate, and react for 8-10 hours under stirring at room temperature , the progress of the reaction was monitored by TLC. After the reaction is complete, the reactant is poured into 100ml of ice water, acidified with glacial acetic acid until no precipitation occurs; the precipitate is filtered, washed with water, dried and purified to obtain a white solid with a yield of 70.5%, m.p.69.8-71.3°C;

[0052] 1 H NMR (600MHz, CDCl 3 )δ7.18(d, J=8.2Hz, 1H, H-11), 7.02(d, J=8.0Hz, 1H, H-12), 6.89(s, 1H, H-14), 4.35(s, 1H),4.29(s,1H),3.39(s,1H),2.89(s,1H),2.83(s,1H),2.45(s,1H),2.44(s,1H),2.43(s,1H ),2.31(d,J=12.0Hz,1H),2.26(d,J=12.4Hz,1H),1.78(s,1H),1.77(s,1H),1.68(s,1H),1.67(s ,1H...

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Abstract

The invention discloses pyrimidine dehydroabietate derivatives and a preparation method and application thereof. The preparation method comprises the following steps: subjecting dehydroabietic acid and 1,2-dibromoethane to a substitution reaction to prepare bromoethyl dehydroabietate; and adding the prepared bromoethyl dehydroabietate into a reaction system by several times, and reacting bromoethyl dehydroabietate with pyrimidine compounds with different substituent groups at room temperature to obtain the pyrimidine dehydroabietate derivatives. The invention provides the novel pyrimidine dehydroabietate derivatives which are short in preparation period, simple to operate and low in cost; the obtained derivatives are high in purity and stable in quality; and experimental results show thatthe antitumor activity of the derivatives can be improved by introducing an antitumor pharmacophore pyrimidine into a dehydroabietic acid skeleton, and the derivatives can be used for preparing antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to dehydroabietic acid pyrimidine derivatives and their preparation methods and applications. Background technique [0002] As one of the leading causes of death in the world, cancer has seriously threatened human health, and the mortality rate has shown a significant upward trend in recent years. Chemotherapy is one of the important steps in tumor treatment; however, chemotherapeutic drugs usually produce cytotoxicity to normal proliferating tissues, and show obvious toxic side effects and drug resistance. Therefore, it is still necessary to find new more effective and less cytotoxic antitumor drugs. [0003] Over the past few decades, researchers have been searching for new anticancer drugs. Among them, natural products played a leading role. In particular, about 60% of antineoplastic drugs currently approved for clinical use come from natural products. Dehydroabietic acid (D...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/56C07D239/38A61P35/00
CPCC07D239/56C07D239/38A61P35/00
Inventor 李芳耀黄琳庞富华李倩李安珂周小群马献力张业
Owner GUILIN MEDICAL UNIVERSITY
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