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3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof

A technology of furostene and dihydroxy, which is applied in the field of chemical biology to achieve good anticancer activity, low toxicity and teratogenicity

Active Publication Date: 2012-08-22
广东固升医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen from the published literature that the structural modification of solanamine mainly focuses on N-alkylation [the following structural formula 2, Frederick C. J Org Chem, 1967, 32 (3): 792-797], or reduction of 5 , on the 6-position double bond (the following structural formula 3, Xiaoming Zha, Hongbin Sun, Jia Hao, et al. Chemistry&Biodiversity, 2007, 4: 25-31), and the shift and functional group transformation of the 5 and 6-position double bond, and The research on the anticancer activity of its products has not been involved so far

Method used

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  • 3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof
  • 3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] 1. Synthesis of compound 3,6-dihydroxy-22(27)imino-4-furostene :

[0030] (1) With 3β, 16β-diacetoxy-26-chloro-5-cholesten-22-one Ⅰ As raw material, using weak base K 2 CO 3 , the selective hydrolysis of 3-acetoxy in a mixture of tetrahydrofuran and methanol (see Cheng Shuilian. Master's Thesis, Yunnan University, Kunming, 2007, p. 20) to obtain 3β-hydroxy-16β-acetoxy- 26-Chloro-5-cholesten-22-one Ⅱ , yield 82%, melting point: 167.0-168.0 ℃;

[0031] (2) Silica-supported pyridinium chlorochromate (PCC) was prepared from concentrated hydrochloric acid, chromium trioxide and silica gel [see Meng Qingyong, Wu Manjiang·Aili, Zhang Lijing, etc. Applied Chemical Industry, 2008, 37(3): 314-316 ], 4.0 g (8 mmol) of compound Ⅱ Dissolve in 100 mL anhydrous CH 2 Cl 2 26 g (48 mmol) PCC carrier reagent was added in batches under stirring, and the reaction was stirred at room temperature for 25 hours. After the reaction was completed, the solvent was removed under reduced p...

Embodiment 2

[0046] Inhibitory effect of 3,6-dihydroxy-22(27)-imino-4-furostene on the growth of tumor cells

[0047] The specific operation method of the activity test: the tumor lines used in the test were purchased from the Cell Resource Center of the Shanghai Institute of Biological Sciences, Chinese Academy of Sciences, and all the tumor lines were cultured in 1640 complete medium containing 10% fetal bovine serum (37°C, 5% CO 2 condition). During the test, the cells in the logarithmic growth phase were adjusted to an appropriate concentration (suspension cells 6×10 4 / mL, adherent cells 5×10 4 / mL) into a 96-well culture plate, 90 mL / well. Set 5 concentrations of the drug, and set 3 parallel wells for each concentration, 10 mL / well, so that the tested concentrations are 0.01, 0.1, 1, 10, 100 mg / mL; blank wells are 100 mL of culture solution, negative control wells Add 10 mL of culture medium to 90 mL of cells; the positive control is the anticancer drug cisplatin. The adherent gr...

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Abstract

The invention provides a compound obtained by shifting 5,6-double bond of solasodine and carrying out functional group conversion, namely 3,6-dihydroxyl-22(27)imino-4-furan sterene. The compound has excellent action of resisting cancer cell growth, is high in activity, and can be used as a raw material for preparing anticancer medicaments for resisting leukaemia, colon cancer, rectum cancer, lung cancer and the like. The invention also provides a preparation method of the compound. The preparation method comprises the step of: based on 3 beta,16 beta-diacetoxy-26-chloro-5-cholestene-22-ketone as a raw material, carrying out 3-acetyl alcoholysis, pyridinium chlorochromate carrier reagent oxidation, reduction, amine cyclization and ring-closing reaction.

Description

Technical field [0001] The present invention involves a kind of chemical and biological technology, especially a compound obtained by structural modification and optimization of Australian eggplane.The compound obtained.The present invention also involves the preparation method of the above compound and the application of anti -cancer drugs. Background technique [0002] Australian tomatoramine (as follows) is the main anticancer activity ingredients of the main anticancer activity of the dragon of the top ten anti -cancer Chinese herbal medicines, Australia's zelatine, and Australian ilcomyl vascopylidine.Due to the toxicity and teratogenicity of eggplane and Australian tomatoine, and Australia's zechida, it is limited to its clinical application. Among them, the existence of 5,6 dual bonds is an important cause of teratogenity. A large number of research has been confirmed to confirmStructural modification synthesis can reduce its toxicity and teratogenicity, and may obtain new...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61P35/00A61P35/02A61P1/00A61P11/00
Inventor 雷泽何健飞孔兰芬
Owner 广东固升医药科技有限公司
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