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1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound as well as preparation method and application thereof

A tetrahydropyridine, 3-d technology, applied in the field of medicine, can solve the problems of fatty liver, steatohepatitis, liver cirrhosis, etc., and achieves the effect of simple preparation route and significant anti-tumor cell proliferation activity.

Active Publication Date: 2022-06-03
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The selective activation of estrogen by tamoxifen may lead to some serious side effects, including thrombosis, stroke and endometrial cancer, etc. Long-term use of tamoxifen may lead to fatty liver, steatohepatitis, liver cirrhosis, extremely Rarely, clinically apparent acute liver injury (Morello KC, Wurz GT, DeGregorio MW. Clinical Pharmacokinetics. 2003,42(4):361–72)

Method used

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  • 1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound as well as preparation method and application thereof
  • 1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound as well as preparation method and application thereof
  • 1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] 2-{[1,3-Dimethyl-2,4-dioxo-7-(pyrrolidin-1-yl)-1,2,3,4-tetrahydropyrido[2,3-d] Preparation of pyrimidin-5-yl]amino}-N-(p-tolyl)acetamide (XQS01)

[0102] Step I: 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (23.25g, 0.15mol), cyanoacetic acid (16.59g, 0.195mol), 150mL acetic anhydride and 3mL of pyridine was placed in a 500mL round bottom flask, heated to 65°C, and kept for 3h. After cooling to room temperature, the resulting precipitate was collected by suction filtration, washed with ethanol, and dried under vacuum to obtain 3-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3, 4-tetrahydropyrimidin-5-yl)-3-oxopropionitrile, off-white solid 27.83g, yield 83.55%.

[0103] Step II: Take a 500mL round bottom flask, first dissolve sodium (4.31g, 0.188mol) in 250mL ethanol, then add 3-(6-amino-1,3-dimethyl-2,4-dioxo- 1,2,3,4-tetrahydropyrimidin-5-yl)-3-oxopropionitrile (27.83g, 0.125mol), after reflux for 1h, the reaction solution was cooled to room temperature, the resulting pre...

Embodiment 2

[0109] 2-{[1,3-Dimethyl-2,4-dioxo-7-(pyrrolidin-1-yl)-1,2,3,4-tetrahydropyrido[2,3-d] Preparation of pyrimidin-5-yl]amino}-N-(m-tolyl)acetamide (XQS02)

[0110] Referring to the preparation method of Example 1, 0.59 g of white solid was obtained, with a yield of 60.20%; m.p.: 228.4-232.1°C; MS: 423.21295[M+H] + ; 1 H NMR (400MHz, DMSO-d 6 )δ10.11(s,1H),9.16(d,J=5.8Hz,1H),7.45(s,1H),7.37(d,J=8.1Hz,1H),7.18–7.20(m,1H), 6.88(d,J=7.4Hz,1H),5.05(s,1H),4.02(d,J=4.8Hz,2H),3.41(s,7H),3.21(s,3H),2.28(s,3H ), 1.92(s,4H).

Embodiment 3

[0112] 2-{[1,3-Dimethyl-2,4-dioxo-7-(pyrrolidin-1-yl)-1,2,3,4-tetrahydropyrido[2,3-d] Preparation of pyrimidin-5-yl]amino}-N-[3-(trifluoromethyl)phenyl]acetamide (XQS03)

[0113] Referring to the preparation method of Example 1, 0.63 g of white solid was obtained, with a yield of 59.70%; m.p.: 271.5-274.6°C; MS: 475.16934[M-H] + ; 1 H NMR (400MHz, DMSO-d 6 )δ10.55(s,1H),9.21(s,1H),8.11(s,1H),7.77(d,J=8.0Hz,1H),7.56(s,1H),7.42(s,1H), 5.11(s,1H), 4.12(s,2H), 3.44(s,3H), 3.40(s,4H), 3.23(s,3H), 1.92(s,4H).

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Abstract

The invention discloses a 1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound as well as a preparation method and application thereof, and belongs to the technical field of medicines. In particular to a 1, 3-dimethyl-1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrimidine compound, and the structural general formula of the compound is as shown in formula (I): R1 is dimethylamino, pyrrolidinyl, morpholinyl or N-methyl piperazinyl; r2 is phenyl, 4-methyl phenyl, 3-methyl phenyl, 2-methyl phenyl, 4-chlorphenyl, 3-chlorphenyl, 4-fluorophenyl, 2-fluorophenyl, 3-trifluoromethyl anilino, 4-trifluoromethyl anilino or 4-trifluoromethoxy anilino. The synthesis method of the compound is simple and convenient, the compound is suitable for industrial production, and biological activity tests show that the compound has anti-tumor activity and can be applied to preparation of anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to 1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine compounds, their preparation method and application. Background technique [0002] Cancer, also known as malignant tumor, is called cancer or tumor in traditional Chinese medicine. It refers to the abnormal proliferation of cells, and these hyperplastic cells may invade other parts of the body. It is a disease caused by the abnormal mechanism of controlling cell division and proliferation. In addition to uncontrolled division, cancer cells can also partially invade the surrounding normal tissues and even transfer to other parts of the body through the internal circulatory system or lymphatic system. But not all tumors become cancerous, and some cell proliferations do not invade other parts of the body, called benign tumors. Common signs and symptoms of cancer include new masses, abnormal bleeding, chronic cough, unexplained w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61P35/00A61K31/519A61K31/5377
CPCC07D471/04A61P35/00
Inventor 胡春谢倩沈燕妮孟艳丽吴阳灿李乐瑢林雪李莹徐钰琳耿金荣
Owner SHENYANG PHARMA UNIVERSITY
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