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2-trifluoromethyl-4-amino-quinoline derivative and application thereof

A technology of trifluoromethyl derivatives, applied in quinoline derivatives and their applications, can solve species-specific nephrotoxicity and other problems

Pending Publication Date: 2021-11-09
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the existing antineoplastic drugs with quinoline as the core are likely to cause species-specific nephrotoxicity and have certain safety risks.

Method used

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  • 2-trifluoromethyl-4-amino-quinoline derivative and application thereof
  • 2-trifluoromethyl-4-amino-quinoline derivative and application thereof
  • 2-trifluoromethyl-4-amino-quinoline derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of compound T1:

[0034] (1) Synthesis of intermediate M3a:

[0035]

[0036]Take 22.0g (64.9mmol) of polyphosphoric acid in a 250mL reaction bottle, add 2.0g (16.2mmol) of p-methoxyaniline, replace the argon, and slowly inject 2.4mL of ethyl trifluoroacetoacetate (16.3 mmol), the injection was completed and the temperature was raised to 110°C and stirred for 4 hours to complete the reaction. The reaction system was poured into ice water and stirred rapidly. It was seen that a large amount of precipitates were precipitated, filtered with suction, and the filter cake was dried under reduced pressure to obtain a total of 3.08g of compound M1a. : 78%. Take 2.00g (8.22mmol) of compound M1a, add 50mL of glacial acetic acid to dissolve it, replace the argon, and slowly inject 0.75mL (9.87mmol) of concentrated nitric acid at 0°C. A large amount of solids were precipitated in the system, which was filtered by suction, washed with water until neutral, and dried to...

Embodiment 2

[0041] Synthesis of compound T2:

[0042]

[0043] Referring to the synthesis method of T1 in Example 1, replacing 4-methoxyaniline with 4-fluoroaniline, compound T2 can be prepared as a red solid with a yield of 48.4%. 1 H NMR (600MHz, CDCl 3 )δ8.19(d,J=9.3Hz,1H),7.53(dd,J=9.3,2.8Hz,1H),6.98(d,J=2.7Hz,1H),6.97–6.91(m,2H), 6.69–6.63(m,2H),3.76(s,3H),3.39(s,3H); 13 C NMR (151MHz, CDCl 3 )δ161.06, 157.51(d, J=240.6Hz), 144.94, 144.24, 143.15, 141.82, 136.78(q, J=36.9Hz), 132.83, 129.10, 125.73, 120.25(q, J=275.9Hz), 116.40(d , J=8.1Hz), 116.11(d, J=22.5Hz), 102.09, 55.82, 39.68; 19 F NMR (565MHz, CDCl 3 ) δ-64.39.

Embodiment 3

[0045] Synthesis of Compound T3:

[0046]

[0047] Referring to the synthesis method of T1 in Example 1, replacing 4-methoxyaniline with p-toluidine and methyl iodide with ethyl iodide, the orange-red solid compound T3 can be prepared with a yield of 60.0%. 1 H NMR (600MHz, CDCl 3 )δ8.16(d, J=9.3Hz, 1H), 7.49(dd, J=9.3, 2.7Hz, 1H), 7.09–6.96(m, 3H), 6.61(d, J=8.5Hz, 2H), 3.81(q, J=7.1Hz, 2H), 3.71(s, 3H), 2.25(s, 3H), 1.31(t, J=7.1Hz, 3H); 13 C NMR (151MHz, CDCl 3 )δ 160.74, 145.00, 144.18, 143.57, 136.76 (q, J = 36.5Hz), 132.59, 130.14, 130.12, 129.98, 125.47, 119.99 (q, J = 275.8Hz), 116.13, 102.72, 55.80, 230.47. ; 19 FNMR (565MHz, CDCl 3 ) δ-64.47.

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PUM

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Abstract

The invention discloses a 2-trifluoromethyl-4-amino-quinoline derivative and application thereof. The 2-trifluoromethyl-4-amino-quinoline derivative comprises a compound as shown in the following general formula I. The compound prepared by the invention is used for preparing an anti-tumor active drug and has a good anti-tumor effect, the stability and the fat solubility of the compound are greatly improved, metabolic capability is not influenced, drug dosage is small, side effects are small, and high safety is achieved.

Description

technical field [0001] The present invention relates to a quinoline derivative and its application, in particular to a 2-trifluoromethyl-4-amino-quinoline derivative and its application. Background technique [0002] Tumor is one of the factors that seriously endanger human health and is currently the second largest cause of morbidity and mortality in the world. Anti-tumor treatments mainly include surgery, radiotherapy, chemotherapy, and immunotherapy. Chemotherapy is the mainstay of treatment for malignant tumors. One of the most effective methods, although the research and development of anti-tumor drugs has achieved some success, but due to the lack of selectivity of most drugs, various toxic side effects, multi-drug resistance and other problems, the existing drugs are far from meeting the clinical needs . [0003] Quinoline alkaloids are a class of heterocyclic compounds containing benzopyridine nitrogen that widely exist in nature and have various pharmacological and...

Claims

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Application Information

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IPC IPC(8): C07D215/44C07D215/46C07D401/12C07D401/04A61P35/00A61K31/4706A61K31/5377A61K31/506A61K31/4709A61K31/498
CPCC07D215/44C07D215/46C07D401/12C07D401/04A61P35/00Y02A50/30
Inventor 徐必学骆衡曾晓萍余佳孟雪玲张偲偲吕梦凡刘锟梁光义
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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