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Barbituric acid chiral cyclohexane spiro compound and its preparation method and use

A technology of spiro compound and barbituric acid, which is applied in the field of barbituric chiral cyclohexane spiro compound and its preparation and application, can solve the problem of unseen barbituric chiral cyclohexane spiro compound. Compound preparation method Antibacterial drugs, no barbituric acid chiral cyclohexane spiro compounds and other problems

Inactive Publication Date: 2017-02-22
CHENGDU UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there are no reports on barbituric chiral cyclohexane spiro compounds; there are also no reports on the preparation method of barbituric chiral cyclohexane spiro compounds and its application to antibacterial drugs

Method used

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  • Barbituric acid chiral cyclohexane spiro compound and its preparation method and use
  • Barbituric acid chiral cyclohexane spiro compound and its preparation method and use
  • Barbituric acid chiral cyclohexane spiro compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080]

[0081] Using propionaldehyde (0.4mmol) and compound 2-a (0.3mmol, commercially available, CAS No. 102-96-5) as raw materials, add (2R)-2-[diphenyl[trimethylsilyloxy]methanol Base]-pyrrolidine as catalyst (0.03mmol), glacial acetic acid (0.04mmol), acetonitrile (1ml) as solvent, stirred at room temperature for 3-4 hours to obtain compound 3-a.

[0082] After the reaction was completed, compound 4-a (0.2mmol), potassium carbonate (0.1mmol dissolved in 1.0mL water) and TBAB (0.01mmol; tetrabutylammonium bromide) were directly added in one pot, and the reaction was stirred at 60°C. The reaction was completely monitored by TLC (thin layer chromatography) to obtain a reaction solution; the reaction solution was spin-dried to solvent, and separated and purified by silica gel column chromatography to obtain 55.9 mg of the compound shown in Formula I-a with a yield of 62%, 94% ee , 94:6dr( 1 H NMR analysis).

[0083] The detection data of the compound shown in formula Ⅰ-a...

Embodiment 2

[0092]

[0093] Using propionaldehyde (0.4mmol) and compound 2-b (0.3mmol, commercially available, CAS No. 102-96-5) as raw materials, add (2R)-2-[diphenyl[trimethylsilyloxy]methanol Base]-pyrrolidine as catalyst (0.03mmol), glacial acetic acid (0.04mmol), acetonitrile (1ml) as solvent, stirred at room temperature for 3 to 4 hours to obtain compound 3-b.

[0094] After the reaction was completed, compound 4-b (0.2mmol), potassium carbonate (0.1mmol dissolved in 1.0mL water) and TBAB (0.01mmol; tetrabutylammonium bromide) were directly added in one pot, and the reaction was stirred at 60°C. The reaction was monitored by TLC (thin layer chromatography) to obtain a reaction solution; the reaction solution was spin-dried to solvent, and separated and purified by silica gel column chromatography to obtain 45.1 mg of the compound shown in formula I-b with a yield of 51%, 98% ee , 85:15dr( 1 H NMR analysis).

[0095] The detection data of the compound shown in formula Ⅰ-b is as ...

Embodiment 3

[0104]

[0105] Using propionaldehyde (0.4mmol) and compound 2-c (0.3mmol, commercially available, CAS No. 102-96-5) as raw materials, add (2R)-2-[diphenyl[trimethylsilyloxy]methanol Base]-pyrrolidine as catalyst (0.03mmol), glacial acetic acid (0.04mmol), acetonitrile (1ml) as solvent, stirred at room temperature for 3 to 4 hours to obtain compound 3-c.

[0106] After the reaction was completed, compound 4-c (0.2mmol), potassium carbonate (0.1mmol dissolved in 1.0mL water) and TBAB (0.01mmol; tetrabutylammonium bromide) were directly added in one pot, and the reaction was stirred at 60°C. The reaction was monitored by TLC (thin-layer chromatography) to obtain a reaction solution; the reaction solution was spin-dried to solvent, and separated and purified by silica gel column chromatography to obtain 52.9 mg of the compound shown in formula I-c, with a yield of 68%, 98% ee , 91:9dr( 1 H NMR analysis).

[0107] The detection data of the compound shown in formula Ⅰ-c is as ...

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Abstract

The invention discloses a cyclohexane barbituric acid chirality spiro-compound indicated in formula I (shown in description) or acceptable salt, hydrate or solvate of the compound in crystal form and pharmacy. R1 and R2 are selected from aryl or substituent aryl respectively or simultaneously; R3, R4 and R5 are selected from hydrogen, C1-C6 alkyl or C1-C6 alkoxy respectively or simultaneously. The novel compound shown in the formula I has restraining effect on one or more kinds of Escherichia coli, xanthomonas maltophilia, Ruofei acinetobacter, staphylocccus aureus and staphylococcus epidermidis, and provides novel choice for screening antiseptic, bacteriostatic and germicidal medicine in clinic practice.

Description

technical field [0001] The invention relates to a barbituric acid chiral cyclohexane spiro compound, a preparation method and application thereof. Background technique [0002] A spiro compound refers to a polycyclic compound in which two monocyclic rings share one carbon atom, and can be used in photochromic materials, electroluminescent materials, pesticides, medicines, etc. [0003] The structures of spiro compounds are different, and their physical and chemical properties are also different, and they all have different uses, such as: spiro compound (a) with anti-mite effect, anti-anxiety drug buspirone hydrochloride (b), delaying arteriosclerosis Hardened spirocyclic indole derivatives (c), non-steroidal anti-inflammatory drug spirocyclic indole derivatives (d), physiologically active drug intermediate azaspirocyclic compound (e), anti-ring bacillus Spiro compounds (f), spiro heterocyclic derivatives with broad-spectrum antibacterial activity (g), spiro compounds with A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/70C07D405/04A61K31/527A61P31/04
CPCC07D239/70C07D405/04Y02A50/30
Inventor 黄维彭成韩波杨磊赵倩冷海军李想王彪谢欣
Owner CHENGDU UNIV OF TRADITIONAL CHINESE MEDICINE
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