Thioether allyl isothiocyanate compounds, and preparation method and applications thereof

A technology for horseradish and compounds, which is applied in the fields of chemical synthesis and biological activity research to achieve the effects of good inhibition effect, obvious killing effect and high yield

Inactive Publication Date: 2016-01-13
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports in the literature on the total synthesis route of thioether horseradish with good anticancer activity.

Method used

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  • Thioether allyl isothiocyanate compounds, and preparation method and applications thereof
  • Thioether allyl isothiocyanate compounds, and preparation method and applications thereof
  • Thioether allyl isothiocyanate compounds, and preparation method and applications thereof

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preparation example Construction

[0039] The present invention provides the preparation method of above-mentioned thioether horseradish, comprising the following steps:

[0040] S1) Dissolve the alkane substituted at both ends in an organic solvent, then add potassium phthalimide and a phase transfer catalyst, heat to 50-80°C, react for 1-8 hours, perform TLC tracking experiment, and then evaporate the solvent , washed with water, and recrystallized from methanol or ethanol to obtain intermediate 1: N-(2-bromoethyl)phthalimide;

[0041] S2) Dissolve intermediate 1 in an organic solvent, add sodium hydrosulfide and a phase transfer catalyst, protect with inert gas, react at 10-50°C for 0.5-12 hours, perform TLC follow-up experiment, wash with water, extract with an organic solvent, and saturated saline After washing and evaporating the solvent, the intermediate 2 was obtained by column chromatography;

[0042] S3) Intermediate 3 is prepared from intermediate 2: a thioether compound. Intermediate 2 reacts with ...

Embodiment 1

[0055] Embodiment 1, intermediate 1: the preparation of N-(2-bromoethyl) phthalic acid imide:

[0056]

[0057] In a 250 mL two-necked flask, 50 mmol of phthalimide, 150 mmol of 1,2-dibromoethane, 2.0 g of TBAB (tetrabutylammonium bromide) phase transfer catalyst and 120 mL of DMF (dimethylformamide) were sequentially added. Heating to 50-80°C, heating and reacting for 5h, TLC monitoring [developing solvent, [V (petroleum ether): V (acetate) = 5:1] until the end of the reaction. The solvent was distilled off under reduced pressure, and the residue was added to ice water. A large amount of white solid appeared, which was suction filtered, washed, and dried. The obtained solid was transferred to a 250 mL dry flask, and 30 mL of methanol was added for recrystallization. After cooling, crystallization, suction filtration, and drying, 10.3 g of a white solid was obtained, with a yield of 81% and a melting point of 75-76°C; 1 HNMR (CDCl 3 ,400MHz), δ:3.62(t,J=6.7Hz,2H),4.11(t,J...

Embodiment 2

[0059] Embodiment two, intermediate 2: the preparation of mercaptan:

[0060]

[0061] The synthesis of mercaptans has been reported in many domestic and foreign literatures. Among them, U.S. Patent US20130210704 reports that bromide reacts with thiourea first, and then undergoes alkalization to prepare mercaptans; in addition, international patent application WO2012082436 and Chinese patent CN201210296425.2 report bromine The compound is reacted with potassium thioacetate to prepare thioester compound, and then acidic hydrolysis is used to prepare mercaptan, and the total yield is less than 60%. The synthesis steps of mercaptans in the prior art are all two-step synthesis. In the present invention, bromide and sodium hydrosulfide are used to prepare mercaptans in one step, which has the advantages of simple process and high yield.

[0062] In a 100 mL two-necked flask, 5 mmol of N-(2-bromoethyl) phthalimide, 6 mmol of sodium hydrosulfide, 0.30 g of TBAB and 60 mL of DMF we...

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Abstract

The invention provides a series of novel thioether allyl isothiocyanate compounds with a general structure disclosed in the invention, and a simple method used for rapid synthesis of the thioether allyl isothiocyanate compounds. According to the method, double-terminal halogen-substituted alkanes are taken as initial raw materials, are reacted with phthalimide potassium so as to introduce N atoms, are reacted with sodium hydrosulfide so as to produce mercaptan, and mercaptan is reacted with benzyl bromide or is reacted with a heterocyclic compound with sulfydryl so as to introduce the thioether structure, an obtained product is reacted with hydrazine hydrate so as to obtain a primary amine, and the primary amine is reacted with an alkali, carbon disulfide, and methylsufonyl chloride so as to prepare the thioether allyl isothiocyanate compounds with heterocyclic nitrogen structures. The method contains few steps; operation is simple; the obtained products can be easily purified; and yield is high. The series of novel thioether allyl isothiocyanate compounds possess obvious killing activity on tumor cells, and possess obvious killing activity on cervical carcinoma cells and lung cancer cells.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and biological activity research, and more specifically, relates to a thioether horseradish, a preparation method and an anticancer activity test thereof. Background technique [0002] Horseradish refers to a class of secondary metabolites extracted from horseradish and other cruciferous plants. Its chemical structure contains -N=C=S active groups. It can be volatilized at room temperature. oily liquid. In 1997, Fuke et al. cultured gastric cancer cells isolated from the human body on a matrix containing 40ug / mL Japanese horseradish crude extract, and found that the morphology of the cancer cells changed significantly, and many cancer cells died at the same time. Fuke et al. At the same time, it was also found that methylthiophenylhexylhorseradin, which naturally exists in cabbage and Japanese horseradish, can inhibit the carcinogenesis of skin cells caused by typical carcinogens (PAHs, HAs and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C331/20C07D257/04C07D285/125A61P35/00
Inventor 王向辉林强史载锋邵艳东朱林华吴禄勇
Owner HAINAN NORMAL UNIV
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