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C5-substituted tetrandrine derivative as well as preparation method and application thereof

A technology of tetrandrine and its derivatives, which is applied in the field of natural medicine and medicinal chemistry, and can solve the problem of little change in pharmacokinetic parameters

Active Publication Date: 2021-03-12
ZHEJIANG MEDICAL COLLEGE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although some researchers have found that the pharmacokinetic parameters of tetrandrine do not change much in animal model tests of anticancer activity, its bioavailability is still a limiting factor. Therefore, research and development have good biological activity and Novel tetrandrine derivatives with pharmacokinetic properties are still in demand in today's market

Method used

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  • C5-substituted tetrandrine derivative as well as preparation method and application thereof
  • C5-substituted tetrandrine derivative as well as preparation method and application thereof
  • C5-substituted tetrandrine derivative as well as preparation method and application thereof

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Embodiment

[0031] Preparation of 5-bromotetrandrine: Dissolve tetrandrine in glacial acetic acid, add tribromopyridinium salt, react for a certain period of time at room temperature, adjust the base of the reaction solution and extract it with dichloromethane, combine the organic layers, and wash with brine , dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 5-bromotetrandrine. 1 H NMR (400MHz, CDC1 3), δ7.34(dd, J=8.2, 2.2Hz, 1H), 7.14(dd, J=8.1, 2.5Hz, 1H), 6.87(s, 2H), 6.79(dd, J=8.3, 2.5Hz, 1H),6.52(s,1H),6.50(s,1H),6.29(dd,J=8.3,2.1Hz,1H),6.01(s,1H),3.93(s,3H),3.79(d,J =10.1Hz,1H),3.74(s,3H),3.55-3.40(m,3H),3.37(s,3H),3.26(dd,J=12.5,5.6Hz,1H),3.22(s,3H) ,3.02-2.95(m,2H),2.91-2.87(m,1H),2.82-2.67(m,5H),2.64(s,3H),2.49(d,J=8.4Hz,1H),2.29(s ,3H); ESI-MS m / z:701.4[M+H] + .

[0032]

[0033] Preparation of 5-cyanotetrandrine (TET-01): Dissolve an appropriate amount of 5-bromotetrandrine in diethylformamide solution, add cuprous cyanide, and keep it warm at ...

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Abstract

The invention discloses a C5-substituted tetrandrine derivative with an amino sulfonation general formula (I), a preparation method thereof and an application of the derivative in preparation of antitumor drugs. The C5-substituted tetrandrine derivative acts on different tumor cells, the activity of different tumor cells after drug treatment is detected by adopting an MTT method, the result showsthat the C5-substituted tetrandrine derivative can effectively induce death of multiple myeloma cells, and compared with tetrandrine, the C5-substituted tetrandrine derivative has the advantages thatthe C5-substituted tetrandrine derivative can effectively induce death of multiple myeloma cells. The C5-substituted tetrandrine derivative disclosed by the invention has obvious anti-cell strain activity, the anti-myeloma RPMI8226 cell strain activity of the C5-substituted tetrandrine derivative is improved by nearly 2 times, and the C5-substituted tetrandrine derivative has good biological activity.

Description

technical field [0001] The invention relates to the fields of natural medicine and medicinal chemistry, in particular to a preparation method of a C5-position substituted tetrandrine derivative. Background technique [0002] Tetrandrine (abbreviated as Tet) is also called tetrandrine, which is the main alkaloid of the dried root of Phyllanthaceae plant and belongs to isoquinoline compound with molecular formula C 38 h 42 N 2 o 6 , chemical formula (6,6',7,12-tetramethoxy-2,2'dimethylberbamine), molecular weight is 622.73g / mol, and its structure is as follows: [0003] [0004] The powder of the Phyllanthaceae plant, the dried root of the herb, the root of this herb is widely cited in the Chinese Pharmacopoeia for the treatment of diseases such as tuberculosis, dysentery, asthma, hyperglycemia, and its anionic and chronotropic effects on the myocardium, malaria, cancer, and fever influences. Tetrandrine is a molecule with a wide range of biological activities, which c...

Claims

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Application Information

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IPC IPC(8): C07D491/18C07D519/00A61P35/00A61P35/02
CPCC07D491/18C07D519/00A61P35/00A61P35/02
Inventor 马安吴水高王越干小仙
Owner ZHEJIANG MEDICAL COLLEGE
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