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7h-[1,2,4]triazol[3,4-b][1,3,4]thiadiazine-phenylhydrazone compounds

A compound, 4-b technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of multidrug resistance limiting clinical application, achieve good inhibitory activity, mild reaction conditions, and simple preparation process Effect

Active Publication Date: 2020-10-09
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, many anti-tumor drugs with good efficacy have been found, such as paclitaxel, camptothecin, vinblastine, etc., but their adverse reactions and multidrug resistance limit their clinical application.

Method used

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  • 7h-[1,2,4]triazol[3,4-b][1,3,4]thiadiazine-phenylhydrazone compounds
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  • 7h-[1,2,4]triazol[3,4-b][1,3,4]thiadiazine-phenylhydrazone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: (E)-3-(2-phenylmethylenehydrazine)-6-(3,4,5-trimethoxyphenyl)-7H-[1,2,4]triazole[ Preparation of 3,4-b][1,3,4]thiadiazine (1)

[0021] (1) 3,4,5-trimethoxyacetophenone (10mmol), N-bromosuccinimide (15mmol), p-toluenesulfonic acid (5mmol) were placed in a round bottom flask, and acetonitrile ( 100ml), reacted at 50°C for 12 hours, stopped the reaction, added saturated sodium thiosulfate solution, extracted with ethyl acetate, combined the organic phases, spin-dried, separated and purified by gel column chromatography to obtain a solid powder with a yield of 67%.

[0022] (2) 2-bromo-1-(3,4,5-trimethoxyphenyl)ethan-1-one (1mmol), 4-amino-3-hydrazino-5-mercapto-1,2,4 -Triazole (1mmol) and benzaldehyde (1mmol) were placed in a round bottom flask, ethanol (10ml) was added, reacted at 80°C for 12 hours, the reaction was stopped, spin-dried, separated and purified by gel column chromatography to obtain a solid powder, the product The structural formula is as follo...

Embodiment 2

[0026] Example 2: (E)-3-(2-(2-methylphenylmethylene)hydrazine)-6-(3,4,5-trimethoxyphenyl)-7H-[1,2 ,4] Preparation of triazol[3,4-b][1,3,4]thiadiazine (2)

[0027] The structural formula of the product is as follows, and the yield is 67%.

[0028]

[0029] 1 H NMR (d 6 -DMSO,400MHz)δ:2.48(s,3H),3.83(s,9H),4.43(s,2H),6.94(s,1H),7.22-7.31(m,3H),7.71(dd,1H) ,8.03(s,1H),8.57(s,1H); EIMS m / z=439[M + ].

Embodiment 3

[0030] Example 3: (E)-3-(2-(3-methylphenylmethylene)hydrazine)-6-(3,4,5-trimethoxyphenyl)-7H-[1,2 ,4] Preparation of triazol[3,4-b][1,3,4]thiadiazine (3)

[0031] The structural formula of the product is as follows, and the yield is 65%.

[0032]

[0033] 1 H NMR (d 6 -DMSO,400MHz)δ:2.35(s,3H),3.83(s,9H),4.42(s,2H),6.95(s,2H),7.25-7.30(m,1H),7.41(dd,1H) ,7.63-7.69(m,2H),8.07(s,1H),8.63(s,1H); EIMS m / z=439[M + ].

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Abstract

The invention discloses a 7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound as well as a preparation method and application thereof. The method comprises the following steps: adding3,4,5-trimethoxy acetophenone, N-bromo-succinimide and p-toluenesulfonic acid into acetonitrile for reacting to obtain 2-bromo-1-(3,4,5-trimethoxy phenyl)ethyl-1-ketone; adding 2-bromo-1-(3,4,5-trimethoxy phenyl)ethyl-1-ketone, 4-amino-3-hydrazino-5-thiol-1,2,4-triazol and a compound (II) into ethanol for reacting to obtain the 7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound(I). The chemical formula of the compound (I) is shown in the description. The chemical formula of the compound (II) is shown in the description. The 7H-[1,2,4]triazole[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound disclosed by the invention has the advantages of remarkable inhibitory activity on the proliferation of tumor cells, simple preparation method, mild reaction conditions, suitabilityfor large-scale industrial production and wide application prospect.

Description

technical field [0001] The invention relates to a 7H-[1,2,4]triazol[3,4-b][1,3,4]thiadiazine-phenylhydrazone compound, a preparation method thereof and an antitumor drug application. Background technique [0002] Malignant tumor is a disease that seriously threatens human health and life. Organic heterocyclic compounds refer to a large class of organic compounds containing heterocyclic structures in their molecular structures. The types are complex and diverse, and they are the largest class of organic compounds. Among the existing marketed drugs, many drugs contain various heterocyclic structures. It is an important method for discovering new drugs to use heterocycles as the mother nucleus for innovative drug development. In addition, phenylhydrazone compounds also have a variety of biological activities, such as anti-inflammatory, anti-tumor, anti-bacterial, anti-microbial and anti-tuberculosis. Based on the above analysis, in order to discover new anti-tumor compounds...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A61P35/00
CPCC07D513/04
Inventor 彭知云王广成
Owner GUIZHOU MEDICAL UNIV
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