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Preparation method and application of diosgenin derivative containing 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment

A technology of diosgenin and derivatives, which is applied in the field of natural medicine and medicinal chemistry, can solve the problems of large side effects and limited use, and achieve significant anti-lung cancer effect

Active Publication Date: 2019-12-13
QIQIHAR MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, although many anti-tumor drugs that have been marketed have good therapeutic effects, their side effects are large, which greatly limits their use. The research and development of anti-tumor drugs is facing severe challenges. The focus of the work of many researchers

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  • Preparation method and application of diosgenin derivative containing 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment
  • Preparation method and application of diosgenin derivative containing 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment
  • Preparation method and application of diosgenin derivative containing 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment

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specific Embodiment approach 1

[0025] Specific Embodiment 1: In this embodiment, diosgenin derivatives containing 1,3,4 oxadiazole or 1,3,4 thiadiazole fragments have a structural formula of R 1 It is an alkyl group containing 1 to 8 carbon atoms, an aromatic ring containing 5 to 12 carbon atoms, an alkoxy-substituted aromatic ring or an aromatic heterocyclic ring containing 5 to 12 carbon atoms, and the aromatic heterocyclic ring includes 1 to 3 heteroatoms of N, O or S, R 2 For H- or acetyl.

specific Embodiment approach 2

[0026] Specific embodiment two: the difference between this embodiment and specific embodiment one is: the R 1 is methyl, phenyl, p-methoxyphenyl, 1-naphthyl or 3-pyridyl.

[0027] Other steps are the same as in the first embodiment.

specific Embodiment approach 3

[0028] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is: the preparation method of diosgenin derivatives containing 1,3,4 oxadiazole fragments is completed according to the following steps:

[0029] said Middle R 2 When it is an acetyl group, it is prepared according to the following steps: Diosgenin is in CH 2 Cl 2And reaction with acetic anhydride in pyridine solvent, obtain intermediate I, intermediate I is in CH 2 Cl 2 and glacial acetic acid by NaBH 3 CN was reduced to intermediate II, which was then oxidized by Jones reagent, tetrahydrofuran and acetone to intermediate III, followed by O-benzotriazole-N,N,N′,N′-tetramethylurea tetrafluoroborate As a coupling catalyst, N,N-diisopropylethylamine and dichloromethane, with acetylhydrazide, benzohydrazide, p-methoxybenzohydrazide, 1-naphthohydrazide or 3-pyridineformoyl Hydrazine condensation to obtain intermediate IV; and then through POCl 3 Dehydration and cycli...

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Abstract

The invention discloses a preparation method and application of a diosgenin derivative containing a 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment, belonging to the technical field of natural medicines and medicinal chemistry. The invention aims to provide the diosgenin derivative which is good in antitumor activity and contains an oxadiazole and thiadiazole fragment. The preparation method comprises the following steps: reacting diosgenin with acetic anhydride in CH2Cl2 and pyridine solvents, carrying out reducing in the presence of CH2Cl2 and glacial acetic acid, carrying out oxidative synthesis, and then performing condensing, dehydrating, cyclizing and hydrolyzing to obtain the diosgenin derivative containing the 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment. The diosgenin derivativeis used for preparing a medicine for treating tumor diseases. The invention relates to the preparation method and the application of the diosgenin derivative containing the 1,3,4-oxadiazole or 1,3,4-thiadiazole fragment.

Description

technical field [0001] The invention relates to the technical field of natural medicine and medicinal chemistry, in particular to derivatives modified with the F ring of diosgenin. Background technique [0002] In recent years, the global cancer incidence and mortality are increasing rapidly, and cancer has become the second leading cause of death after cardiovascular and cerebrovascular diseases. According to the latest World Cancer Annual Report, from 2006 to 2016, the number of cancer deaths increased by 17.8%. In 2018, there were about 18 million new cases and 9.6 million cancer deaths worldwide. Malignant tumors have become an important killer of human health. However, although many anti-tumor drugs that have been marketed have good therapeutic effects, their side effects are large, which greatly limits their use. The research and development of anti-tumor drugs is facing severe challenges. focus of many researchers. [0003] Natural products have always been an impor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00
CPCC07J71/0005A61P35/00
Inventor 王文豹张金玲王雪梅杨吉芳郭丽娜孙辑凯王晓丽宋波
Owner QIQIHAR MEDICAL UNIVERSITY
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