C5-position substituted tetrandrine derivatives and preparation method and application thereof

A technology of tetrandrine and bromidentine, which is applied in the field of preparation of tetrandrine derivatives substituted at the C5-position, can solve the problem of little change in pharmacokinetic parameters and achieve obvious anti-cell line activity , good biological activity, and the effect of improving the activity of cell lines

Active Publication Date: 2022-04-01
ZHEJIANG MEDICAL COLLEGE +1
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  • Abstract
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  • Claims
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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

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  • C5-position substituted tetrandrine derivatives and preparation method and application thereof
  • C5-position substituted tetrandrine derivatives and preparation method and application thereof
  • C5-position substituted tetrandrine derivatives and preparation method and application thereof

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Embodiment

[0031] 5-bromine anti-hexametin prepare: Han anti-hexametin is dissolved in glacial acetic acid, add tribrompyridium salt, reaction at room temperature for a certain time, reaction liquid nodide, combined with dichloromethane, combined with saline , Dry sodium sulfate, dry, to give 5-bromoan anti-hexarin. 1 H NMR (400MHz, CDC1 3), Δ7.34 (DD, J = 8.2, 2.2 Hz, 1H), 7.14 (DD, J = 8.1, 2.5 Hz, 1H), 6.87 (S, 2H), 6.79 (DD, J = 8.3, 2.5 Hz, 1H), 6.52 (S, 1H), 6.50 (S, 1H), 6.29 (DD, J = 8.3, 2.1 Hz, 1H), 6.01 (S, 1H), 3.93 (S, 3H), 3.79 (D, J = 10.1 Hz, 1H), 3.74 (S, 3H), 3.55-3.40 (m, 3H), 3.26 (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 = 8.4 Hz, 1H), 2.29 (S , 3H); ESI-MS M / Z: 701.4 [M + H] + .

[0032]

[0033] Preparation of 5- Cyanyl Han anti-hexametin (TET-01): Take a proper amount of 5-bromo-anthropide in diendylformamide solution, add cyanide, allowed to heat insulation at 140-150 ° ...

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Abstract

The invention discloses a C5-position substituted tetrandrine derivative with aminosulfonated general formula (I), a preparation method thereof and an application for preparing an antitumor drug. Using the C5-position substituted tetrandrine derivatives of the present invention to act on different tumor cells, using the MTT method to detect the activity of different tumor cells after drug treatment, it was found that the C5-position substituted tetrandrine derivatives of the present invention can Effectively induce multiple myeloma cell death. Compared with tetrandrine itself, the C5-position substituted tetrandrine derivative of the present invention has obvious anti-cell line activity, and its anti-myeloma RPMI-8226 cell line activity is improved Nearly 2 times, with good biological activity.

Description

Technical field [0001] The present invention relates to the field of natural drugs and pharmaceutical chemistry, and in particular, there is a method of preparing a C5-position replacing the Han anti-hexin derivative. Background technique [0002] Han defense has also called Tets, also called powder, anti-fibrine, for anti-cultural plant powder, has a main alkaloid, azinoline compound, and molecular formula C. 38 Hide 42 N 2 O 6 , Chemical formula (6, 6 ', 7, 12-tetramethoxy-2, 2' dimethyl), the molecular weight is 622.73 g / mol, and the structure is as follows: [0003] [0004] Anti-scientific plant powder is dry root, the root of this herb is widely referred to in China's pharmacopoeia, the treatment of tuberculosis, dysentery, asthma, high blood sugar, etc. Influence. Han defense has a molecule with extensive bioactive activity that can be with CA 2+ Non-competitive confrontation, with calcium channel blocking effect, a slow channel blocker. For decades, as my country's cl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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