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Benzoic acid derivatives and application thereof

A derivative, benzoic acid technology, applied in the field of benzoic acid derivatives

Inactive Publication Date: 2019-03-08
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is still no effective drug to treat tumors, so the study of anti-tumor drugs has become a hot topic today

Method used

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  • Benzoic acid derivatives and application thereof
  • Benzoic acid derivatives and application thereof
  • Benzoic acid derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 (preparation CJ-1-1)

[0034] The structural formula is (CJ-1-1) The preparation method of compound is as follows:

[0035]

[0036] Dissolve 1mmol of 3-nitro-4-methoxybenzoic acid in DMF, add 1.2mmol of TEA, then add 1.1mmol of HOBT, 1.2mmol of EDCI, and finally add 1mmol of 3,4,5-trimethoxyaniline. TLC monitoring, after the reaction was completed, water was added to precipitate a yellow solid. The obtained product was identified by nuclear magnetic resonance and mass spectrometry, and the identification result was 1 H NMR (CDCl 3 )δ7.66(s,1H),δ7.275-7.281(d,1H),δ7.229-7.256(m,1H),δ6.97(s,2H),δ6.85-6.87(d,1H ),δ3.95(s,3H),δ3.91(s,6H),δ3.86(s,3H).MS(ESI)m / z 361.57(M-H) - .Anal.(C 17 h 14 N 2 o 3 ) C, H, N, O. According to the above identification results, the obtained product is CJ-1-1.

Embodiment 2

[0037] Embodiment 2 (preparation CJ-1-2)

[0038] The structural formula is (CJ-1-2) The preparation method of the compound is the same as CJ-1-1, and the obtained product is identified by nuclear magnetic resonance and mass spectrometry, and the identification result is 1 H NMR(DMSO)δ8.10-8.11(dd,1H),δ7.98-8.01(dd,1H),δ7.84(s,1H),δ7.15(dd,1H),δ7.10(s ,2H),δ4.00(s,3H),δ3.96(s,6H),δ3.94(s,3H).MS(ESI) m / z 362.47(M+H) + .Anal.(C 17 h 18 N 2 o 7 ) C, H, N, O. According to the above identification results, the obtained product is CJ-1-2.

Embodiment 3

[0039] Embodiment 3 (preparation CJ-1-3)

[0040] The structural formula is (CJ-1-3) The preparation method of compound is as follows:

[0041]

[0042] Dissolve 1mmol 3-nitro-4-methoxybenzoic acid in DMF, add TEA1.2mmol, add HOBT1.1mmol, EDCI1.2mmol, DMSP 0.02mmol, and finally add 3,4,5-trimethoxyphenol 1 mmol. TLC monitoring, after the completion of the reaction, add water to precipitate a solid. The obtained product was identified by nuclear magnetic resonance and mass spectrometry, and the identification result was 1 H NMR (CDCl 3 )δ8.69(s,1H),δ8.37-8.39(d,1H),δ7.22-7.24(d,1H),δ6.49(s,2H),δ4.10(s,3H), δ3.88(s,9H).MS(ESI)m / z 385.70(M+Na) +.Anal.(C 17 h 17 NO 8 ) C, H, N, O. According to the above identification results, the obtained product is CJ-1-3.

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Abstract

The invention relates to benzoic acid derivatives. The chemical structure of the benzoic acid derivatives is shown as formula (I) in the description, wherein in the formula (I), X is O or NH; R<1> is3,4,5-trimethoxy, 3-nitro-4-methoxy or 3-amino-4-methoxy; R<2> is 3,4,5-trimethoxy, 3-nitro-4-methoxy or 3-amino-4-methoxy. The benzoic acid derivatives have anti-tumor bioactivity.

Description

technical field [0001] The invention relates to organic compounds, in particular to benzoic acid derivatives, which can be used to prepare medicines for treating diseases. Background technique [0002] Tumor has become the second largest killer of human health, seriously endangering the quality of human life. At present, there is still no effective drug to treat tumors, so the study of anti-tumor drugs has become a hot topic today. At present, the structures of anti-tumor drugs are complex and diverse, and compounds with different structures show excellent anti-tumor activities. The mechanism of anti-tumor drugs mainly includes inhibiting the synthesis of substances necessary for tumor cell growth, such as protein, DNA, nucleic acid, etc., inhibiting tubulin polymerization or depolymerization, and killing tumors by improving autoimmunity. Anti-tumor drugs developed based on different mechanisms mainly include alkylating agents, antimetabolites, anti-tumor antibiotics, anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/59C07C229/64C07C235/56C07C237/44C07C205/43C07C219/34A61P35/00
CPCA61P35/00C07C205/43C07C205/59C07C219/34C07C229/64C07C235/56C07C237/44
Inventor 陈建军李玲吕琳全东令
Owner SOUTHERN MEDICAL UNIVERSITY
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