Vanillylamine/vanillyl alcohol derivatives as well as preparation method and application thereof

A technology of vanillol and derivatives, applied in the field of medicine, can solve problems such as the rise of alanine aminotransferase, and achieve the effects of easy synthesis, improved properties and activities

Active Publication Date: 2016-10-19
EAST CHINA NORMAL UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The fifth-generation cephalosporin Ceftapipro has antibacterial activity against Gram-positive bacteria, Gram-negative bacteria and anaerobic bacteria. It is the first anti-methicillin-resistant Staphylococcus aureus (MRSA) Staphylococcus aureus (VRSA) is effective cephalosporins, but when multiple doses are infused, there are individual phenomena of headache and mild to moderate alanine aminotransferase (ALT) increased adverse reactions

Method used

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  • Vanillylamine/vanillyl alcohol derivatives as well as preparation method and application thereof
  • Vanillylamine/vanillyl alcohol derivatives as well as preparation method and application thereof
  • Vanillylamine/vanillyl alcohol derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] compound i a Synthesis:

[0056]

[0057] 5-Nitrofuran-2-carboxylic acid (0.16 g, 1 mmol), vanillylamine hydrochloride (0.19 g, 1 mmol), EDC (0.27 g, 1.5 mmol) and HOBt (0.19 g, 1.5 mmol) were dissolved in N, In N-dimethylformamide (10mL), after stirring for 10min, 3-picoline (0.26mL) was added to the above reaction solution, and after stirring for 18h, 30ml of saturated sodium bicarbonate solution and 30ml of ethyl acetate were added to extract The organic phase was washed three times with saturated brine, dried with anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (ethyl acetate:petroleum ether=1:2) to obtain the product vanilla amide derivative i a (R 1 =5-nitrofuryl, R 2 =H) 0.20g, yield: 65%; white solid; 1 H NMR (400MHz, DMSO) δ9.29(t, J=5.8Hz, 1H), 8.87(s, 1H), 7.74(d, J=3.9Hz, 1H), 7.43(d, J=3.9Hz, 1H ),6.91(s,1H),6.72(s,2H),4.35(d,J=6.0Hz,2H),3.75(s,3H). 13C NMR (101MHz, DMSO) δ155.93, 151.43, 148.31, 147.41, 145...

Embodiment 2

[0060] compound i b Synthesis:

[0061]

[0062] The synthetic method refers to Example 1, wherein 5-nitrothiophene-2-carboxylic acid is substituted for 5-nitrofuran-2-carboxylic acid to obtain the product vanillic amide derivative i b (R 1 =5-nitrothienyl, R 2 =H)0.48g, yield: 68%; white solid; 1 H NMR (400MHz, DMSO) δ9.59(t, J=5.5Hz, 1H), 8.92(s, 1H), 8.13(d, J=4.3Hz, 1H), 7.94(d, J=4.4Hz, 1H ),6.93(s,1H),6.75(d,J=8.1Hz,2H),4.36(d,J=5.8Hz,2H),3.75(s,3H). 13 CNMR (101MHz, DMSO) δ159.28, 152.80, 147.43, 146.58, 145.71, 130.15, 129.30, 127.44, 120.07, 115.25, 112.13, 55.59, 42.70. MS (ESI) calcd for C 13 h 12 N 2 o 5 S::309.4[M+H] + .

Embodiment 3

[0064] compound i c Synthesis

[0065]

[0066] The synthetic method refers to Example 1, wherein 5-(4-nitrophenyl)-2-furancarboxylic acid is substituted for 5-nitrofuran-2-carboxylic acid to obtain the product vanilla amide derivative i c (R 1 =5-(4-nitrophenyl)-2-furyl, R 2 =H)0.33g, yield: 48%; brown solid; 1 H NMR (400MHz, DMSO) δ9.12(t, 1H), 8.85(s, 1H), 8.32(d, J=8.7Hz, 2H), 8.18(d, J=8.7Hz, 2H), 7.42(d ,J=3.4Hz,1H),7.28(d,J=3.4Hz,1H),6.93(s,1H),6.74(s,2H),4.39(d,J=5.8Hz,2H),3.76(s ,3H). 13 C NMR (101MHz, DMSO) δ157.22, 152.19, 148.70, 147.41, 146.64, 145.56, 135.17, 130.05, 125.07, 124.29, 119.94, 115.88, 115.26, 112.00, 111.53, 9630, 45 19 h 16 N 2 o 6 : 369.5[M+H] + .

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Abstract

The invention relates to vanillylamine/vanillyl alcohol derivatives as well as a preparation and an application thereof. The vanillylamine/vanillyl alcohol compound has good antibacterial activity, and is especially suitable for the application to preparation of antibacterial medicines due to inhibition effects for drug resistant strains; the invention belongs to the technical field of medicine as well as preparation and application of medicine.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a vanillyl amine / vanillyl alcohol derivative and a preparation method and application thereof. Background technique [0002] Bacterial infection is the most common type of infectious disease, especially clinical drug-resistant strains, and the resistance to multiple antibiotics is constantly increasing. At present, there are only a few antibiotics that are really effective against clinical drug-resistant strains, and the commonly used drugs are vancomycin, daptomycin, linezolid and ceftazidime. Vancomycin can inhibit the synthesis of bacterial cell walls, and has strong effects on Staphylococcus aureus, Streptococcus pyogenes, Streptococcus pneumoniae, etc., but bacteria that can resist vancomycin have appeared, such as vancomycin-resistant enterococci ( VRE). Daptomycin is the second generation of glycopeptide antibiotics after vancomycin, used to treat complicated skin and ski...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/71C07D333/44C07D307/68A61P31/04
Inventor 杨帆李佳杨财广潘雪莹汤杰倪腾凤于丽芳
Owner EAST CHINA NORMAL UNIV
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