Isosorbide-monoimidazole salt compounds and preparation method thereof

A salt compound, isosorbide technology, applied in organic chemistry, drug combination, antipyretic, etc.

Inactive Publication Date: 2017-03-08
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Combine isosorbide with good biological activity and imidazole and its derivatives to form isosorbide-monoimidazole sa

Method used

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  • Isosorbide-monoimidazole salt compounds and preparation method thereof
  • Isosorbide-monoimidazole salt compounds and preparation method thereof
  • Isosorbide-monoimidazole salt compounds and preparation method thereof

Examples

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preparation example Construction

[0018] The preparation method specifically includes:

[0019] A, the preparation of compound isosorbide mesylate:

[0020] Using isosorbide as raw material, mesylate esterification with methanesulfonyl chloride in anhydrous pyridine: dissolve isosorbide in anhydrous pyridine, add methanesulfonyl chloride dropwise at 0 °C, the molar ratio of the dosage is Isosorbide: methanesulfonyl chloride = 1: 2.5, the amount of anhydrous pyridine is 20 ml: 1g isosorbide, after stirring and reacting at room temperature for 20 hours, dichloromethane was added for dilution (30ml: g substrate), and water ( 50 ml) and saturated brine (50 ml), the organic phase was washed with anhydrous NaSO 4 Dry, filter, and concentrate the solvent under reduced pressure, add water (30 ml), raise the temperature to 55°C and stir for 2 hours until the precipitate is completely dissolved, then cool it to room temperature, a white solid precipitates, filter, and use ethanol for precipitation (30 ml) was washed r...

Embodiment 1

[0026] Preparation of compound 5a: see the above preparation methods A, B, and C;

[0027]

[0028] Compound 5a: Formula C 18 h 19 BrN 2 o 3, Yield 90%. White solid powder, mp 181-186 o c. 1 H NMR (300 MHz, DMSO-d 6 ): δ 8.10 (1H, s), 8.08 (1H, s), 7.80-7.73 (2H, m), 7.67-7.62 (2H, m), 7.58 (1H, s), 6.94 (1H, d, J = 2.1 Hz), 6.15 (2H, s), 5.71 (1H,d, J = 4.5 Hz), 5.25-5.18 (3H, m), 4.18 (1H, d, J = 10.8 Hz), 3.72-3.67 (1H, m), 2.69 (3H, s). 13 C NMR (75 MHz, DMSO-d 6 ): Δ 191.04, 150.79, 146.06, 134.51,133.66, 128.96, 128.41, 123.22, 118.70, 99.53, 86.35, 84.21, 62.81,54.92, 54.51, HRMS (ESI-TOF) M / Z Calcd FOR C 18 h 19 N 2 o 3 + [M-Br] + 311.1390, found 311.1389.

Embodiment 2

[0030] Preparation of compound 5b: see the above preparation methods A, B, and C;

[0031]

[0032] Compound 5b: Formula C 18 h 18 Br 2 N 2 o 3, Yield 82%. White solid powder, mp 164-167 o c. 1 H NMR (300 MHz, DMSO-d 6 ): δ 8.03 (1H, s), 8.00 (1H, s), 7.89 (1H, s), 7.86 (1H, s),7.72 (1H, s), 7.58 (1H, s), 6.93 (1H, d , J = 2.4 Hz), 6.14 (2H, s), 5.70 (1H, d, J = 3.0 Hz), 5.25-5.18 (3H, m), 4.18 (1H, d, J = 10.8 Hz), 3.71-3.66 (1H,m), 2.68 (3H,s). 13 C NMR (75 MHz, DMSO-d 6 ): Δ 190.45, 150.79, 146.08, 132.74,132.03, 130.37, 128.60, 123.18, 118.71, 99.53, 86.33, 84.20, 62.82,54.90, 54.92. HRMS (ESI-TOF) M / Z Calcd FOR COR COR C 18 h 18 BrN 2 o 3+ [M-Br] + 389.0495, found 389.0496.

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Abstract

The invention discloses a series of isosorbide-monoimidazole salt compounds with a structural formula (as shown in a figure I or figure II) and a preparation method of the isosorbide-monoimidazole salt compounds. The preparation method includes: adopting isosorbide as a raw material, performing reaction with methylsulfonyl chloride under an anhydrous pyridine condition to obtain isosorbide methanesulfonate, subjecting to thermal reaction with 2-methylimidazole or 5,6-dimethyl benzimidazole in an anhydrous DMF (dimethyl formamide) solvent to synthesize isosorbide-monoimidazole, and performing reflux reaction with alkyl bromide in a methylbenzene solvent to synthesize the isosorbide-monoimidazole salt compounds. The isosorbide-monoimidazole salt compounds show great analgesic effects.

Description

technical field [0001] The invention relates to a novel isosorbide-monoimidazolium salt compound, a preparation method thereof, and an analgesic application of a pharmaceutical composition in which the compound is an active ingredient. Background technique [0002] In recent years, rational molecular hybridization between pharmacophore or active compounds, as a new strategy for drug discovery, has received great attention from synthetic and medicinal chemists. By hybridizing two pharmacophores with the same or different pharmacological activities, such a synthetic method can not only increase the affinity for a single target of a receptor that affects a certain disease, but also act on two or two receptors at the same time. The above targets have double or even multiple effects on the treatment of diseases. Many novel compounds designed through molecular hybridization exhibit diverse biological activities and are currently widely used in various fields. [0003] Isosorbide...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61P29/00A61P25/04
CPCC07D493/04
Inventor 杨丽娟李燕华朱亮杨淬黄超杨丽
Owner YUNNAN MINZU UNIV
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