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A technology of alkyl and compound, applied in the field of medicine, can solve problems such as toxic and side effects
Active Publication Date: 2014-12-24
SHENYANG PHARMA UNIVERSITY
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Cytotoxic drugs can kill tumor cells, but they lack selectivity for cancer cells and normal cells, so they have strong toxic and side effects. Looking for targeted anti-tumor...
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Embodiment 1
[0317] Example 1: (E)-N 1 -[2-(6-(4-Methylpiperidinyl)methylbenzo[d]thiazolyl)]-N 4 Preparation of -(2,4-dimethoxybenzaldehyde)semicarbazone
[0318] The preparation of step A N-(4-nitrobenzyl) diethylamine (1)
[0319] Add p-nitrobenzyl bromide (10.8g, 0.05mol) to 50mL of acetonitrile, add 10 times the amount of diethylamine, react at room temperature for 3h, add water to the reaction system, extract with dichloromethane three times, and dry the dichloromethane layer , evaporated to dryness to give 9.4g yellow liquid, yield: 90%, MS [MH + ] (m / z): 209.3.
[0320] Preparation of step B 4-(diethylaminomethyl)aniline (2)
[0321] Add intermediate 1 (10.4g, 0.05mol) to 100mL ethanol, raise the temperature to 70°C, add ferric chloride (2.8g, 0.001mol) and activated carbon (0.18g, 0.015mol), keep at 70°C, drop Add hydrazine hydrate (25g, 0.5mol), drop it, reflux for 5h, suction filter while it is hot, concentrate the ethanol solution, add water, extract three times with dichlo...
Embodiment 2
[0332] Example 2(E)-N 1 -[2-(6-(Diethylamino)methylbenzo[d]thiazolyl)]-N 4 -(4-Methoxybenzaldehyde)semicarbazone
[0333] ESI-MS [M+H] (m / z): 412.2;
Embodiment 3
[0334] Example 3(E)-N 1 -[2-(6-(Diethylamino)methylbenzo[d]thiazolyl)]-N 4 -(3-bromo-4-hydroxybenzaldehyde)semicarbazone
[0335] ESI-MS [M+H] (m / z): 476.1;
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Abstract
The invention belongs to the technical field of medicine, and relates to semicarbazone derivatives disclosed as general formula I, and geometrical isomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein the substituent groups M, R1, R2, R and n are defined in the specification. The invention also relates to a method for preparing compounds disclosed as Formula I, a pharmaceutical composition containing the compounds and application of the compounds and pharmaceutical composition in preparing drugs for treating and/or preventing cancers and other hyperplastic diseases.
Description
technical field [0001] The invention belongs to the technical field of medicine, relates to semicarbazone derivatives and their uses, in particular to semicarbazone derivatives, their pharmaceutical compositions, and their preparation of cell proliferation inhibitors for the treatment and / or prevention of various cancers. Uses in medicine. Background technique [0002] Tumor is a disease that seriously threatens human life and health. In recent years, the incidence and mortality of tumors have been increasing year by year. Cytotoxic drugs can kill tumor cells, but they lack selectivity for cancer cells and normal cells, so they have strong toxic and side effects. Looking for targeted anti-tumor drugs that can selectively kill cancer cells and have no effect on normal proliferating cells Drugs have become an important direction for the development of new anticancer drugs. [0003] Apoptosis is an autonomous and orderly death process regulated by genes. From the perspective...
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