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Alkaloid with antitumor activity as well as preparation method and application thereof

An anti-tumor activity, alkaloid technology, applied in anti-tumor drugs, organic active ingredients, organic chemical methods, etc., can solve the problem of no cytotoxicity, achieve high industrial application prospects, good biocompatibility, and yield. high rate effect

Pending Publication Date: 2022-05-06
TIBET UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the combination of these alkaloids and tumor necrosis factor-related apoptosis-inducing ligand (TNF-related apoptosis-inducing ligand, TRAIL) showed significant cytotoxicity, while the compound itself did not show cytotoxicity

Method used

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  • Alkaloid with antitumor activity as well as preparation method and application thereof
  • Alkaloid with antitumor activity as well as preparation method and application thereof
  • Alkaloid with antitumor activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation of each compound specifically comprises the following steps:

[0058] Synthesis of compound 2

[0059] Compound 1 (N-tert-butoxycarbonyl-N-methylethylenediamine) (500 mg) was dissolved in redistilled THF (tetrahydrofuran) (12 mL), and n-butyl lithium (2.4M in THF, 1.05mL), stirred at -50°C for 30min to obtain solution A; dissolved crotonic acid (258.27mg) in redistilled THF (5mL), and added N-methylmorpholine (0.325mL) at -10°C, Then slowly add isobutyl chloroformate (0.375mL) and stir at -10°C for 15min, the reaction solution becomes white and turbid. Slowly add solution A to solution B at -50°C, stir at -50°C for 30min, then stop the reaction, add saturated ammonium chloride to quench, and extract the aqueous phase with EA (ethyl acetate) (10mL×3), The organic phases were combined, washed with saturated brine (10 mL), dried with anhydrous sodium sulfate, filtered, evaporated under reduced pressure and spin-dried to obtain a yellow oil, which was left...

Embodiment 2

[0096] Example 2 Product H-1 to H-6 antitumor activity test

[0097] The products H-1 to H-6 prepared in Example 1 were tested for antitumor activity, and the specific steps are as follows:

[0098] The growth inhibitory activity of various tumor cells was screened by MTT method, and doxorubicin was used as a positive control drug at the same time. Digest the cells in the logarithmic growth phase with 0.25% trypsin, prepare a single-cell suspension, and inoculate 3000-4000 cells / well in a 96-well plate according to the difference in cell growth rate, and add 100 μL of cell suspension to each well . After 24h, add the concentration of 10μmol L -1 Add 100 μL (final concentration of DMSO 50 .

[0099] The growth inhibitory activity of various cancer cells was screened by MTT method, and adriamycin was used as a positive control drug. Table 1 shows the effects of products H-1 to H-6 on prostate cancer cells LNcaP, human cervical squamous cell carcinoma cells SiHa, human The s...

Embodiment 3

[0103] Example 3 Product H-3 Antitumor Activity Test

[0104] According to the method in Example 2, alkaloid H-3 was tested for prostate cancer cell LNcaP, human breast cancer cell MCF-7, human cervical squamous cell carcinoma cell SiHa, and human prostate cancer cell PC-3 at different concentrations. inhibition.

[0105] Table 2 shows the survival rate of alkaloid H-3 to LNcaP, MCF-7, SiHa, PC-3 at different concentrations detected by MTT method.

[0106] Table 2 The survival rate of alkaloid H-3 to LNcaP, MCF-7, SiHa, PC-3 at different concentrations detected by MTT method

[0107]

[0108] It can be seen from the data in Table 2 that the concentration of alkaloid H-3 at 10 μmol L -1 The concentration has a certain inhibitory rate on LNcaP, MCF-7, SiHa, PC-3 cells.

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Abstract

The invention relates to the technical field of alkaloid synthesis, in particular to alkaloid with anti-tumor activity and a preparation method and application thereof, and the molecular structure of the alkaloid is any one shown in H-1 to H-14. The alkaloid with the anti-tumor activity is non-toxic, good in biocompatibility and easy to absorb and metabolize by organisms, and can be used for preparing anti-tumor drugs. The compound has an inhibiting effect on at least one of prostate cancer cells LNcaP, human breast cancer cells MCF-7, human cervical squamous carcinoma cells SiHa and human prostate cancer cells PC-3, and has the advantages of simple synthesis route, high reaction efficiency, high yield and higher industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of synthesizing alkaloids, in particular to an alkaloid with antitumor activity, its preparation method and application. Background technique [0002] Alkaloids are a large category of natural products, and they are also the natural product category with the most complex structures and the most diverse biological activities. Natural products have always been one of the hottest research fields of organic chemists around the world. Nowadays, the discovery and application of more and more new methods and synthetic methods have promoted the synthesis of natural products, such as Heck coupling, Suzuki coupling, Shapless asymmetric epoxidation, and so on. The synthesis of natural products can be divided into the synthesis of terpenoids, steroids, aromatics (simple phenylpropanoids, lignans, flavonoids) and alkaloids according to their sources, among which alkaloids are widely found in animals and plants , bacter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/153C07D491/22C07D491/056C07D491/20A61P35/00C07F7/18A61K31/695A61K31/407A61K31/4741A61K31/4747
CPCC07D491/153C07D491/22C07D491/056C07D491/20A61P35/00C07F7/1804C07F7/188C07B2200/07
Inventor 洪学传田甜乔雪
Owner TIBET UNIV
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