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: 2014-03-26
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 relates to the field of chemical and biological technology, in particular to a compound obtained by structural modification and optimization of solanamine, more specifically to a shift of double bonds at the 5 and 6 positions of solanamine and its functional group Converted compound. The present invention also relates to a preparation method of the above compound and its application in the preparation of anticancer drugs. Background technique [0002] Solanamine (structural formula 1 below) is the aglycon of steroidal alkaloids such as Solasonine and Solamargine, the main anticancer active ingredients of Nightshade Solanum, one of the top ten anticancer Chinese herbal medicines. Due to the toxicity and teratogenicity of solanamine and solanine, their clinical application is limited. Among them, the existence of double bonds at positions 5 and 6 is an important cause of teratogenicity, and a large number of studies have confirmed...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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