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Novel heterocyclic aromatic hydrazone derivative, pharmaceutically acceptable salt, preparation method and application thereof

A technology of heterocyclic aromatic hydrazones and derivatives, which is applied in the field of medicine, can solve the problems of drugs with low toxic and side effects, and achieve the effects of low toxic and side effects, simple synthesis, and novel preparation methods

Active Publication Date: 2020-01-21
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few drugs that use the degradation of tumor ferritin to play an anti-tumor effect and have little toxic side effects

Method used

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  • Novel heterocyclic aromatic hydrazone derivative, pharmaceutically acceptable salt, preparation method and application thereof
  • Novel heterocyclic aromatic hydrazone derivative, pharmaceutically acceptable salt, preparation method and application thereof
  • Novel heterocyclic aromatic hydrazone derivative, pharmaceutically acceptable salt, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: 5-(4-Chlorophenyl)-2-(2-(bis(pyridin-2-yl)methylene)hydrazino)thiazole

[0050]

[0051] Preparation method: In a fume hood, under dry conditions, in a 25mL single-necked round bottom flask, add 10mmol of dipyridone and 10.25mmol of thiosemicarbazide to 10ml of absolute ethanol, and then add two drops of ice Acetic acid catalyst, stirred and reacted at 80°C for about 4 hours, TLC followed the reaction, after the reaction was completed, let it stand for cooling, the precipitated solid was filtered and dried, then dissolved and recrystallized with absolute ethanol, and the recrystallized white crystal was obtained as intermediate.

[0052] Take 0.25mmol of the above-mentioned intermediate and place it in a 25mL single-necked round bottom flask, add 5ml of ethanol to dissolve, then add α-bromo-4-chloroacetophenone, add a magnet, stir the reaction at room temperature, and follow the reaction by TLC. After about 4h Finish the reaction, filter and wash with eth...

Embodiment 3

[0057] Example 3: 4-(2-Chlorophenyl)-2-(2-(bis(pyridin-2-yl)methylene)hydrazino)thiazole

[0058]

[0059] The preparation method is the same as in Example 1, except that α-bromo-2-chloroacetophenone is used instead of α-bromo-4-chloroacetophenone in Example 1 to obtain the yellow powdery target compound. The combined yield of the two steps is 82%. Confirmation data for the target compound: 1 H NMR (600MHz, DMSO-d 6 )δ14.14(s,1H),8.90(d,J=5.1Hz,1H), 8.60(d,J=4.8Hz,1H),7.99(q,J=6.9,6.4Hz,2H),7.96– 7.89(m,2H),7.86(d,J=7.8Hz,1H),7.65(s,1H),7.62(d,J=8.0Hz,1H),7.58(dd,J=7.6,5.0Hz,1H ), 7.50–7.43(m,2H),7.38(dd,J=8.0,2.1Hz,1H).

Embodiment 4

[0060] Example 4: 2-(2-(bis(pyridin-2-yl)methylhydrazino)-4-(4-fluorophenyl)thiazole

[0061]

[0062] The preparation method is the same as in Example 1, except that α-bromo-4-fluoroacetophenone is used instead of α-bromo-4-chloroacetophenone in Example 1 to obtain the yellow powdery target compound. The combined yield of the two steps is 80%. The confirmation data for the target compound is: 1 H NMR (600MHz, DMSO-d6) δ8.96(d, J=5.1Hz, 1H), 8.60(d, J=5.0Hz, 1H), 8.19(t, J=7.2Hz, 1H), 8.07(t ,J=7.8Hz,1H),8.01(d,J=8.0Hz,1H),7.94–7.87(m,2H),7.79(d,J=8.1Hz,1H),7.73(t,J=6.5Hz ,1H),7.54(dd, J=7.5,5.0Hz,1H),7.47(s,1H),7.26(t,J=8.9Hz,2H).

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Abstract

The invention relates to a novel heterocyclic aromatic hydrazone derivative, a pharmaceutically acceptable salt, a preparation method and an application thereof. The thiazole aromatic hydrazone derivative comprises a structural general formula I and an optical isomer of the structural general formula I, wherein in the structural general formula I, the R represents aromatic hydrocarbon, heterocyclic ring or substituent with aromatic hydrocarbon and heterocyclic ring at the same time; r1 is a heterocycle. In the invention, heterocycles such as thiophene are added to one side of hydrazone, and atleast one pyridine group is introduced to a carbon atom on the other side of hydrazone, wherein these groups are all drug active groups in different fields; therefore, the plurality of target spots are integrated into a whole through a specific connection relationship to form a new drug, and the new drug has excellent anti-cancer activity, small toxic and side effects and simple and convenient synthesis, and can be well applied to industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to novel heterocyclic aromatic hydrazone derivatives, novel heterocyclic aromatic hydrazone derivatives for preventing and treating tumors, pharmaceutically acceptable salts thereof, and preparation methods and applications thereof. Background technique [0002] Cancer is a disease with a very high fatality rate, and many types of cancer cannot be cured. Therefore, anti-tumor drugs have always been the research focus and hotspot in the fields of medicine, chemistry, optics or interdisciplinary technology. At present, there are many drugs or potential drugs with anti-cancer activity. Most of the anti-cancer drugs used clinically interfere with or block the proliferation process of cells. They are generally called cytotoxic drugs. Chemotherapy drugs are roughly divided into the following categories according to their action 4 categories. (1) Inhibition of DNA synthesis: Interfering ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C07D417/12A61P35/00
CPCC07D417/14C07D417/12A61P35/00
Inventor 闫超黄腾飞徐天琦
Owner NANJING UNIV
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