Alpha-biphenyl-N-alkyl nitrone compound and synthetic method thereof

A technology of alkyl nitrones and compounds, which is applied in the field of α-biphenyl-N-alkyl nitrones and their synthesis, can solve the difficulties of free radical detection, short half-life of spin adducts, free radical adducts Slow formation speed and other problems, to achieve the effect of increasing steric hindrance, increasing lipophilicity, and weakening enzyme catalytic quenching

Inactive Publication Date: 2008-07-23
ZHEJIANG UNIV
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Problems solved by technology

[0008] The existing PBN-type spin trapping agents have the problems of slow addition of free radicals, and short half-life of spin adducts due to disproportionation quenching of free radical adducts or enzyme-catalyzed quenching in organisms. It brings certain difficulties to the detection of free radicals, especially free radicals in the body, so it is necessary to design and synthesize new free radical spin capture agents to solve them

Method used

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  • Alpha-biphenyl-N-alkyl nitrone compound and synthetic method thereof
  • Alpha-biphenyl-N-alkyl nitrone compound and synthetic method thereof
  • Alpha-biphenyl-N-alkyl nitrone compound and synthetic method thereof

Examples

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Embodiment 1

[0056] The synthesis of embodiment 1α-(2-phenyl) phenyl-N-tert-butylnitrone

[0057] 1) Synthesis of 2-phenylbenzaldehyde: add 1.85 grams (10mmol, 1.0eq) of 2-bromobenzaldehyde, 1.83 grams (15mmol, 1.5eq) of phenylboronic acid, 6.9 grams (30mmol, 3.0 eq) of potassium phosphate hydrate, 0.58 g (5mol%) of Pd(Ph 3 P) 4 and 50 mL of toluene, heated to 80° C. for 2.5 hours under nitrogen protection. After the reaction, lower the temperature to room temperature, add 50mL of water and stir for 5 minutes, extract with ethyl acetate (50mL×3), combine the organic phases, and successively use 10mL of 1N sodium hydroxide aqueous solution, 100mL of water and 100mL of saturated saline Wash each time. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (ethyl acetate / petroleum ether=1 / 5) to obtain 1.78 g of 2-phenylbenzaldehy...

Embodiment 2

[0059] Example 2 Synthesis of α-[2-(2-methylphenyl)]phenyl-N-tert-butylnitrone

[0060] 1) Synthesis of 2-(2-methylphenyl)benzaldehyde: replace the phenylboronic acid in Example 1 with 2.04 grams (15mmol, 1.5eq) of 2-methylphenylboronic acid, with 1.9 milligrams (0.02mol%) Pd 2 (dba) 3 +0.8 milligrams of N,N-diisopropyl-2-dicyclohexylphosphine benzamide instead of Pd(Ph 3 P) 4 , the reaction temperature is 60 DEG C, reacted for 20 hours and separated and purified according to the method of Example 1 to obtain 0.78 g of 2-(2-methylphenyl)benzaldehyde, with a yield of 40%. 1 HNMR (400MHz, CDCl 3 ): δ9.78(s, 1H), 8.05(d, J=8.0Hz, 1H), 7.64(t, J=7.6Hz, 1H), 7.51(t, J=7.2Hz, 1H), 7.36-7.27 (m, 4H), 7.20 (d, J=7.2Hz, 1H), 2.12 (s, 3H).

[0061] 2) Synthesis of α-[2-(2-methylphenyl)]phenyl-N-tert-butylnitrone: with 0.392 grams (2mmol, 1.0eq) of 2-(2-methylphenyl)benzene Formaldehyde replaces the 2-phenylbenzaldehyde in Example 2, and reacts and separates and purifies according...

Embodiment 3

[0062] Example 3 Synthesis of α-[2-(4-methylphenyl)]phenyl-N-tert-butylnitrone

[0063] 1) Synthesis of 2-(4-methylphenyl)benzaldehyde: replace phenylboronic acid in Example 1 with 2.04 grams (15mmol, 1.5eq) of 4-methylphenylboronic acid, and react for 12 hours according to Example 1 method And separation and purification treatment, 1.52 grams of 2-(4-methylphenyl)benzaldehyde was obtained, with a yield of 78%. 1 H NMR (400MHz, CDCl 3 ): δ9.96(s, 1H), 8.02(d, J=8.8Hz, 1H), 7.62(t, J=7.6Hz, 1H), 7.49-7.43(m, 2H), 7.28(s, 4H) , 2.43(s, 3H).

[0064] 2) Synthesis of α-[2-(4-methylphenyl)]phenyl-N-tert-butylnitrone: 0.392 grams (2mmol, 1.0eq) of 2-(4-methylphenyl)benzene Formaldehyde replaces the 2-phenylbenzaldehyde in Example 2, and reacts and separates and purifies according to the method of Example 2 to obtain α-[2-(4-methylphenyl)]phenyl-N-tert-butylnitrone 0.16 g, 30% yield. MS(ESI): m / z 268.1(M+H); 1 H NMR (400MHz, CDCl 3 ): δ9.31(d, J=6.8Hz, 1H), 7.48(s, 1H), 7.40-7...

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Abstract

The invention discloses an alpha-xenyl-N-alkyl nitro ketones compound of which the structural formula is as shown in formula (I). The synthetic method is: first adding the benzene boric acid and the bromo benzaldehyde into the toluene which carry on the Suzuki coupling reaction to produce biphenyl formaldehyde under the existence of the potassium phosphate hydrate and the palladium catalyst. Then mixing the biphenyl formaldehyde, 2-nitryl-2- alkyl propane and zinc powder together in the ethyl alcohol, adding ethanoic acid, and put into the refrigerator for refrigeration, then separated for depuration. The alpha-xenyl-N-alkyl niter ketones compound connects aromatic group on the PBN benzene ring, and can increase the steric hindrance of the free radical addition atom and weaken the disproportionation extinguishment of the free radical addition compound or the enzyme catalyzed extinguishment inside the organism thus to increase the life of the free radical addition compound. The nitro alkone compound can be effective reagent for examining the free radicals in the lipin system like cell membrane.

Description

technical field [0001] The invention relates to α-biphenyl-N-alkylnitrone compounds used as hydroxyl radical detection reagents and a synthesis method thereof. Background technique [0002] As an important intermediate of chemical reactions, free radicals widely exist in nature and around people's lives. Many chemical reactions and life phenomena are related to free radicals. Free radicals are necessary in life activities, but they can also cause harm. [0003] Research in life sciences has shown that oxygen- and / or nitrogen-containing free radicals are continuously produced in aerobic organisms. Under normal conditions, mitochondria are the main source of oxygen free radicals. Free radicals can react with any biomolecules (proteins, liposomes, sugars, DNA) to change their structure and function. Living organisms have a rich antioxidant system that prevents free radicals from damaging other molecules. [0004] A large body of evidence shows that superoxide and nitric ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/48C07C249/10
Inventor 吴金龙廖宇戴静朱明江刘珊林
Owner ZHEJIANG UNIV
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