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Butenolide structure-containing benzyl amino dithio formiate compounds, and preparation method and application thereof

A technology of benzylcarbamate and butenolactone, which is applied in the field of medicinal chemistry to reduce costs and increase antifungal activity

Active Publication Date: 2011-09-14
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Combining the active unit of butenolactone with carbamate to synthesize a new type of benzyl carbamate compound containing butenolactone structure, there is no relevant literature report so far

Method used

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  • Butenolide structure-containing benzyl amino dithio formiate compounds, and preparation method and application thereof
  • Butenolide structure-containing benzyl amino dithio formiate compounds, and preparation method and application thereof
  • Butenolide structure-containing benzyl amino dithio formiate compounds, and preparation method and application thereof

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preparation example Construction

[0018] Compound 6 was prepared with reference to the following literature:

[0019] (a) B. Morgan, D. Dolphin, R. H. Jones, T. Jones, F. W. B. Einstein, J. Org. Chem. 52 (1987) 4628-4631. (b) H. S Yang, X. X. Qiao, Q. Cui, X. H. Xu, Chin. Chem. Lett. 20 (2009) 1023-1023.

Embodiment 1

[0020] Example 1, Synthesis of α-Bromo-γ-butyrolactone (Compound 2)

[0021] Under the condition of ice bath, slowly drop 6.4mL (125mmol) liquid bromine into the mixture of 10g (116mol) γ-butyrolactone and 13.4g (432mol) red phosphorus; mL (125mmol) liquid bromine. After the dropwise addition was completed, the reaction was maintained at 80°C for 3 h. Cool and blow in air continuously for 1 h to blow away excess liquid bromine and hydrogen bromide generated. Then the temperature was raised to 80°C, and 1.5 mL of distilled water was slowly added dropwise, and 20 mL of water was added after the reaction eased, and refluxed for 4 hours. After cooling, the layers were separated, and the aqueous layer was extracted three times with ether; the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 19.6 g of crude compound 2.

Embodiment 2

[0022] Example 2, Synthesis of α-phenylene sulfide-γ-butyrolactone (compound 3)

[0023] Under the conditions of ice-salt bath and nitrogen protection, 5.1g (94 mmol) of sodium methoxide was added to 350mL of dry methanol, and then 12.6mL (122mmol) of thiophenol was added dropwise. After 15 min, a solution of 15.57 g (94 mmol) of compound 2 in 100 mL THF (tetrahydrofuran) was added and added dropwise slowly for 1 h. Remove the ice bath and stir at room temperature for 2 h. Evaporate the solvent under reduced pressure, add 200mL ethyl acetate, add diatomaceous earth and suction filter, combine the washed ethyl acetate, and then successively wash with saturated NaHCO 3 aqueous solution, NaOH aqueous solution and distilled water extraction. The ethyl acetate phase was collected and dried over anhydrous magnesium sulfate. After filtering and evaporating the solvent under reduced pressure, 18.67 g of the crude product of compound 3 was obtained.

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Abstract

The invention discloses butenolide structure-containing benzyl amino dithio formiate compounds, and a preparation method and application thereof, and belongs to the field of medicinal chemistry. The structure is shown as the general formula I, wherein R1 is C1-C5 alkyl or hydrogen; R2 is C1-C5 alkyl or hydrogen; and R3 is hydrogen, methyl monosubstituted or multisubstituted at different positions, methoxy, fluorine, chlorine or hydroxyl and the like. The preparation method comprises the following steps of: adding a CS2 solution into benzylamine or substituted benzylamine and an aqueous solution of alkaline substances dropwise; stirring; adding 3-bromomethyl-gamma-butyrolactone; reacting with stirring; and performing recrystallization or column chromatography separation to prepare the butenolide structure-containing benzyl amino dithio formiate compounds. The butenolide structure-containing benzyl amino dithio formiate compounds have obvious inhibition effect on fungi such as candida albicans, grayish purple penicillium, aspergillus niger and the like, and have important significance for further researching novel antifungal medicaments and developing medicaments with proprietary intellectual property rights.

Description

technical field [0001] The invention relates to a class of carbamodithiocarbamate derivatives, in particular to benzyl carbamodithiocarbamate compounds containing a butenolactone structure, a preparation method and application thereof, and belongs to the field of medicinal chemistry. Background technique [0002] As an important class of organic reaction intermediates, carbadithiocarbamate compounds can be used to synthesize trifluoromethylamine compounds, heterocyclic compounds and tetrathiofulvalene superconducting materials. In addition, due to its wide range of biological activities, such as antibacterial, anti-inflammatory, insecticidal, anti-tumor, anti-radiation and chelating heavy metals, it has attracted extensive attention in the fields of agricultural chemistry and medicinal chemistry. In 1995, Mehta, R. G. et al. extracted a natural carbamate-Brassinin with chemical anti-cancer effects from cruciferous plants (Mehta, R. G.; Liu, J. etc. Carcinogenesis 1995, 1...

Claims

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Application Information

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IPC IPC(8): C07D307/58A01N47/14A01P1/00A01P3/00
Inventor 刘宏民王晓娟郑甲信徐海伟郭琳琳陈广威郭晓郑晨星
Owner ZHENGZHOU UNIV
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