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Drug for preventing and treating bronchogenic carcinoma and preparation method thereof

A drug and pharmacy technology, applied in the directions of drug combination, pharmaceutical formula, medical preparation containing active ingredients, etc., can solve the problem of difficult to cure lung cancer, and achieve the effect of good in vitro anti-tumor activity and outstanding inhibitory effect.

Inactive Publication Date: 2018-09-28
佳木斯大学附属第一医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the existing treatment methods are difficult to cure lung cancer, therefore, it is necessary to develop more drugs for the prevention and treatment of lung cancer

Method used

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  • Drug for preventing and treating bronchogenic carcinoma and preparation method thereof
  • Drug for preventing and treating bronchogenic carcinoma and preparation method thereof
  • Drug for preventing and treating bronchogenic carcinoma and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1: Preparation of 4-((4-tert-butyl-2-(quinolin-3-yl)-4,5-dihydro (Azol-5-yl)methyl)phenol (compound 1)

[0074]

[0075] Put 5mmol quinoline-3-nitrile, 10mmol 4-(3-amino-2-hydroxy-4,4-dimethylpentyl)phenol, 0.5mmol sulfur, and 100ml toluene in a round bottom flask and heat under stirring To reflux, react for 10 hours. The reaction was monitored by TLC. After the reaction, it was cooled to room temperature, unreacted sulfur was filtered, and toluene was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate / cyclohexane (1:3) as the mobile phase to obtain a white color. Solid 4-((4-tert-butyl-2-(quinolin-3-yl)-4,5-dihydro The azol-5-yl)methyl)phenol is 1.46 g, and the yield is 81.0%.

[0076] Mass spectrum (ESI): 360.18[M+H] +

[0077] Proton spectrum (400MHz, DMSO) δ9.63(s,1H),9.42(s,1H),8.94(s,1H),7.63-7.91(m,4H),7.15(d,2H),6.73(d, 2H), 3.62 (m, 1H), 2.89 (d, 2H), 1.54 (m, 1H), 0.96 (s, 9H).

Embodiment 2

[0078] Example 2: Preparation of 3-(5-(2,4-dichlorophenyl)-4-propyl-4,5-dihydro (Azol-2-yl)quinoline-7-amine (compound 2)

[0079]

[0080] Substitute 7-aminoquinoline-3-carbonitrile for quinoline-3-carbonitrile in Example 1, and substitute 3-amino-1-(2,4-dichlorophenyl)hexyl-2-ol for 4-(3 -Amino-2-hydroxy-4,4-dimethylpentyl)phenol, other operations are the same as in Example 1, to obtain 3-(5-(2,4-dichlorophenyl)-4-propyl-4, 5-dihydro (Azol-2-yl)quinoline-7-amine, the yield was 76.1%.

[0081] Mass spectrum (ESI): 414.11 [M+H] +

[0082] Proton spectrum (400MHz, DMSO) δ9.31(s,1H),8.89(s,1H),8.62(d,1H),7.94(s,1H),7.64(s,1H),7.42(s,1H) , 7.35(d, 1H), 7.16(d, 1H), 5.64(s, 2H), 3.65(m, 1H), 2.85(d, 2H), 1.53(m, 1H), 1.32(m, 2H), 1.23 (m, 2H), 0.91 (t, 3H).

Embodiment 3

[0083] Example 3: Preparation of 2-(5-fluoroquinoxalin-2-yl)-5-(4-(pyrrolidin-1-yl)benzyl)-4,5-dihydro Azole (compound 3)

[0084]

[0085] Use 5-fluoroquinoxaline-2-nitrile instead of quinoline-3-nitrile in Example 1, and use 1-amino-3-(4-(pyrrolidin-1-yl)phenyl)propane-2-ol Instead of 4-(3-amino-2-hydroxy-4,4-dimethylpentyl)phenol, other operations were the same as in Example 1, to obtain 2-(5-fluoroquinoxalin-2-yl)-5-( 4-(pyrrolidin-1-yl)benzyl)-4,5-dihydro Azole, the yield is 69.3%.

[0086] Mass spectrum (ESI): 377.17[M+H] +

[0087] Proton spectrum (400MHz, DMSO)δ8.75(s,1H), 7.62(d,1H), 7.53(t,1H), 7.30(d,1H), 7.14(d,2H), 6.74(d,2H) , 3.64 (m, 1H), 3.44 (t, 4H), 2.85 (d, 2H), 1.98 (t, 4H), 1.53 (d, 2H).

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Abstract

The invention relates to a drug for preventing and treating bronchogenic carcinoma and a preparation method of the drug. The compound has good in-vitro antitumor activity, and has obvious inhibition effect for human lung cancer cell A-549 and non-small cell lung cancer NSCLC, compared with known anticancer drugs, the inhibition effect is equivalent or more prominent, and the drug is suitable for being used for preventing or treating bronchogenic carcinoma, especially for primary bronchogenic carcinoma.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry. Specifically, the present invention relates to a medicine for preventing or treating bronchial lung cancer and a preparation method of the medicine. Background technique [0002] Primary bronchial lung cancer, also called lung cancer, is the most common primary malignant tumor of the lung. It is currently the world's first cause of cancer death. Most lung cancers originate from the bronchial mucosal epithelium, so it is also called bronchial lung cancer. In the past 50 years, the incidence and mortality of lung cancer have risen rapidly in various countries in the world, especially in industrialized countries. Among male patients who died of cancer, lung cancer has ranked first, and the incidence of lung cancer in women is particularly increasing. . Lung cancer has become a major killer that seriously threatens the health and lives of people all over the world, and its danger cannot be unde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A61K31/4709A61K31/498A61P35/00
CPCC07D413/04
Inventor 窦鹏挥骆鹏刘雪竹李晶桑立珠
Owner 佳木斯大学附属第一医院
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