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Synthesis and application of imine spiro piperidine compounds

A compound, piperidine technology, applied in the field of medicine, can solve the problem that the new compound inhibits the antibacterial activity of chitin synthase and has not been reported.

Inactive Publication Date: 2020-07-21
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the novel compounds involved in the present invention have not been reported in terms of inhibiting chitin synthase activity and antibacterial activity.

Method used

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  • Synthesis and application of imine spiro piperidine compounds
  • Synthesis and application of imine spiro piperidine compounds
  • Synthesis and application of imine spiro piperidine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of 2-ethyl-2,7-diazaspiro[4.4]nonane-1,3,6,8-tetraone

[0025] 2.04 g (11 mmol) of compound 2, 1.68 g (15 mmol) of bromoethane, 0.44 g (11 mmol) of triethylamine were added to a 50 mL round-bottomed flask, 20 mL of DMF was added as a solvent, and the temperature was 60°C. Under heating and stirring overnight, the solvent was removed by distillation under reduced pressure, ethyl acetate was added while hot to stir and dissolve, the solution was adjusted to acidity with dilute hydrochloric acid, the organic layer was obtained by separation, and ethyl acetate and petroleum ether were used to pass the column to obtain a white solid 1.22 g ( 5.8 mmol), yield 53%.

Embodiment 2

[0026] Example 2: Preparation of 2-(2-bromoethyl)-7-ethyl-2,7-diazaspiro[4.4]nonane-1,3,6,8-tetraone

[0027] 5.13 g (24.4 mmol) of compound 3, 1.17 g (29.3 mmol) of sodium hydroxide, 7.3 g (39 mmol) of 1,2-dibromoethane and 30 mL of DMF were added to a 100 mL round-bottomed flask, and the mixture was heated at 80 °C. Under the conditions of heating and stirring overnight, the solvent was distilled off under reduced pressure, water and ethyl acetate were added while hot, the organic layer was obtained by liquid separation, and ethyl acetate and petroleum ether were used to pass through the column to obtain 4.48 g (14 mmol) of yellow solids in a yield of 58 %. 1H NMR (600 MHz, CDCl3) δ 4.06–3.89 (m, 2H), 3.61 (dd, J = 14.2, 7.1 Hz, 2H), 3.57 (t, J= 6.5 Hz, 2H), 3.37–3.24 (m, 2H), 2.84–2.71 (m, 2H), 1.20 (t, J= 7.2 Hz, 3H).

Embodiment 3

[0028] Example 3: N-(3-Bromophenyl)-1-(2-(7-ethyl-1,3,6,8-tetraoxo-2,7-diazaspiro[4.4]nonane- 2-yl)ethyl)piperidine-4-carboxamide hydrochloride

[0029]In a 25 mL flask, 0.254 g (0.8 mmol) of intermediate compound 4, 0.272 g (0.96 mmol) of intermediate 4-piperidinecarboxylic acid derivative (N-(3-bromophenyl) piperidine-4-carboxamide) were added ), 0.132 g (0.96 mmol) of ground potassium carbonate, a catalytic amount of KI, 3 mL of acetonitrile, heated and stirred at 70 °C for 4 h, filtered, and passed through a column with ethyl acetate to obtain 0.24 g of a viscous liquid, After the liquid was acidified with concentrated hydrochloric acid, the liquid was removed and recrystallized to obtain 0.14 g of white crystals with a yield of 25%. 1H NMR (600 MHz, DMSO-d6) δ 10.91 (d, J= 152.1 Hz, 1H), 10.34 (d, J = 7.3 Hz, 1H), 7.99 (d, J= 27.8 Hz, 1H), 7.53 (dt , J= 11.9, 5.9 Hz, 1H), 7.33–7.17 (m, 2H), 3.95–3.80 (m, 2H), 3.69–3.40 (m, 4H), 3.35–2.91 (m, 8H), 2.72 (d , J=120.6 Hz, ...

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Abstract

The invention discloses design, synthesis and application of novel imide spiro compounds. The structure of the compounds is shown as a general formula I shown in the specification, wherein R is a benzene ring or a substituted benzene ring. Bioactivity test experiments prove that most compounds show certain inhibitory activity on candida albicans, aspergillus flavus, cryptococcus neoformans and aspergillus fumigatus, and also have certain inhibitory activity on chitin synthase.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to a kind of N-(2-(7-ethyl-1,3,6,8-tetraoxo-2,7-diazaspiro[4,4]nonane-2 Design and synthesis of -yl)ethyl)piperidine-4-carboxamides and their application in antimicrobial. Background technique [0002] In recent years, the morbidity and mortality of invasive fungal infections have increased significantly, and fungal infections are a serious threat to human health. Some antifungal drugs currently used in clinical practice are greatly restricted in their application due to their narrow spectral activity and large nephrotoxic side effects. Poisonous antifungal drugs. Spiro compounds have rigid structures and stable structures, and have important applications in medicine, pesticides, various materials, asymmetric catalysis, etc., and have biological activities in anti-fungal, anti-inflammatory, anti-cancer, treatment of mental illness, and anti-diabetes. . In recent years, the applications o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10A61K31/454A61P31/04A61P31/10
CPCC07D487/10A61P31/04A61P31/10Y02A50/30
Inventor 吉庆刚黄焱容李百慧
Owner SOUTHWEST UNIV
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