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Organic nitrite donor as well as preparation method and medical application thereof

A kind of nitrite, donor technology, applied in organic nitrite donor compound and its preparation, application in myocardial ischemia and pulmonary arterial hypertension medicine, preparation prevention or treatment of cerebral ischemia field, can solve unreported biological activity It can reduce the volume of cerebral infarction and cerebral water content, reduce the volume of cardiac ischemia, and improve hemodynamics.

Active Publication Date: 2021-01-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, only one literature mentions that 2-nitromethylcyclohexenone (RD, the same below) can be released rapidly under the attack of nucleophile But it has not been reported to have any biological activity (J Am Chem Soc,2006,128(50):16332-16337)

Method used

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  • Organic nitrite donor as well as preparation method and medical application thereof
  • Organic nitrite donor as well as preparation method and medical application thereof
  • Organic nitrite donor as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1: (E)-2-nitromethyl-1,3-diphenyl-2-en-1-one (I 1 ) preparation

[0072]

[0073] (a) Dissolve propiophenone (1.34g, 10.0mmol, 1.0eq) in 20mL of absolute ethanol, add benzaldehyde (1.17g, 11.0mmol, 1.1eq), NaOH (1.2g, 30.0mmol, 3.0eq), React overnight at 70°C. The reaction solution was acidified to pH 2-3 with dilute hydrochloric acid, then extracted with ethyl acetate (30 mL), the organic layer was washed three times with water and saturated brine, dried over anhydrous sodium sulfate, concentrated, and column chromatography (petroleum ether / ethyl acetate Ester=100 / 1, v / v) to obtain colorless oil V 1 , yield 65%. ESI-MS(m / z):223.1[M+H] + ; 1 H NMR (300MHz, CDCl 3 ): δ7.72–7.78(m,2H),7.51–7.58(m,1H),7.31–7.50(m,7H),7.18(d,1H,J=1.4Hz),2.28(d,3H,J = 1.4Hz); 13 C NMR (75MHz, CDCl 3 ): δ199.21, 142.08, 138.43, 136.72, 135.65, 131.57, 129.68, 129.33, 128.59, 128.31, 128.16, 14.37.

[0074] (b) put V 1 (222.1mg, 1.0mmol, 1.0eq) was dissolved in 15mL of...

Embodiment 2

[0076] Example 2: (E)-3-(2,5-dimethoxyphenyl)-2-nitromethyl-1-phenylprop-2-en-1-one (I 2 ) preparation

[0077]

[0078] Referring to the synthetic method of Example 1. ESI-MS(m / z):328.1[M+H] + ; 1 H NMR (300MHz, MeOD) δ7.75(d, J=7.9Hz, 2H), 7.58(t, J=7.2Hz, 1H), 7.46(s, 2H), 7.31(s, 1H), 7.09(s ,1H),6.98–6.73(m,2H),5.59(s,2H),3.75(s,3H),3.68(s,3H). 13 C NMR (75MHz,MeOD)δ197.50,153.80,150.78,140.04,137.23,132.39,129.15,127.96,122.87,115.97,115.46,112.99,112.73,111.39,66.63,54.838,54.7

Embodiment 3

[0079] Embodiment 3: (E)-3-(4-methoxyphenyl)-2-nitromethyl-1-phenylprop-2-en-1-ketone (I 3 ) preparation

[0080]

[0081] Referring to the synthetic method of Example 1. ESI-MS(m / z):298.1[M+H] + ; 1 H NMR (300MHz, CDCl 3 )δ7.83(d, J=8.4Hz, 2H), 7.58(s, 1H), 7.51(t, J=7.3Hz, 2H), 7.35–7.21(m, 3H), 6.98(d, J=8.8 Hz,2H),5.64(s,2H),3.73(s,3H). 13 C NMR (75MHz, CDCl 3 )δ196.61, 149.04, 144.00, 132.95, 131.23, 129.67, 128.49, 125.82, 124.02, 118.30, 114.71, 72.24, 58.34.

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Abstract

The invention relates to the field of medicinal chemistry, in particular to an organic nitrite donor compound(structures shown in a general formula I and a general formula II)containing a 1nitromethyl2phenylethylene skeleton, a preparation method of the organic nitrite donor compound, and medical application of a medicinal composition of the compounds to prevention or treatment of cerebral ischemia, myocardial ischemia and pulmonary hypertension.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an organic nitrite containing 1-nitromethyl-2-phenylethylene skeleton Donor compounds (general formula I or II) and preparation methods thereof, as well as pharmaceutical compositions containing these compounds and their medical uses, especially in the preparation of drugs for the prevention or treatment of cerebral ischemia, myocardial ischemia and pulmonary hypertension application. Background technique [0002] Studies over the past 10 years have shown that sodium nitrite (NaNO 2 ) has a good therapeutic and protective effect on some cardiovascular and cerebrovascular diseases, especially ischemic diseases (Nature, 2008, 453(7199): 1194-1195). [0003] Intravenous injection of sodium nitrite during ischemia-reperfusion in rats with cerebral ischemia can reduce their infarct volume, increase local blood flow, and improve neurological function (Stroke, 2006, 37(11):2744-275...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/45C07C205/04C07C317/22C07C255/35A61P9/12A61P9/10A61K31/12A61K31/10A61K31/277A61K31/04
CPCC07C205/45C07C205/04C07C317/22C07C255/35A61P9/12A61P9/10Y02A50/30
Inventor 张奕华黄张建吴建兵
Owner CHINA PHARM UNIV
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