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Triazoles compounds with antimicrobial activity and preparation method and pharmaceutical use thereof

A compound, triazole technology, applied in the field of new triazole compounds, can solve the complicated treatment of deep fungal infection and other problems, and achieve the effect of low cost, easy to obtain raw materials, and simple synthesis method

Inactive Publication Date: 2009-06-03
SOUTHWEST UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, drug-drug interactions complicate the treatment of deep fungal infections

Method used

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  • Triazoles compounds with antimicrobial activity and preparation method and pharmaceutical use thereof
  • Triazoles compounds with antimicrobial activity and preparation method and pharmaceutical use thereof
  • Triazoles compounds with antimicrobial activity and preparation method and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: (E)-3-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)- 2-propen-1-one (compound 1a for short) and (Z)-3-(4-chlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4 Preparation of -triazol-1-yl)-2-propene-1-one (compound 1b for short)

[0030] Add 2.23g (0.01mol) 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, 4-chloro 1.41g (0.01mol) of benzaldehyde, 0.5mL of hexahydropyridine and 40mL of toluene, install a water separator, reflux condenser, and heat to reflux for 6h under the protection of nitrogen. After cooling slightly, it was washed with saturated brine, and the organic phase was separated. The aqueous phase was extracted with chloroform (20 mL×3), the organic phases were combined, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel column chromatography to obtain 2.61 g of a light yellow solid, namely compound 1a, with a yield of 75.4%; Melting point: 102-104°C; at the same time, 0.45 g of another light...

Embodiment 2

[0031] Example 2: Hydroxylation of (E)-1-[3-(3,4-dichlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4- Preparation of triazol-1-yl)allyl]piperidinium (referred to as compound 2)

[0032] Compound 2 was synthesized according to the preparation method of compound 1, and the starting material was 2.23 g of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (0.01mol), 3,4-dichlorobenzaldehyde 1.75g ​​(0.01mol), the product obtained is light yellow solid 2.52g, is compound 2, productive rate: 65.8%; m.p.141~143 ℃; UV-vis ( CH 3 OH)λ max : 205, 296nm; IR (KBr): 3121.3 (Ar-H, =C-H), 1603.8, 1498.6, 1427.3 (aromatic ring skeleton, C = C), 842.8 (=C-H) cm -1 ; 1 HNMR (300MHz, CDCl 3 )δ: 8.06(d, 1H, triazole3-H), 8.04(d, 1H, triazole5-H), 6.60~7.40(m, 7H, Ar-H, C=CH), 2.88~2.90(t, 4H, piperidine 2,6-H)1.50~1.72(m,6H,piperidine 3,4,5-H)ppm; 13 C NMR (300MHz, CDCl 3 )δ: 192.1 (C=N + -), 167.1, 163.7, 154.4, 152.5, 145.2, 136.9, 135.4, 133.9, 132.5, 132.3., 131.9, 131.1, 128.5...

Embodiment 3

[0033] Example 3: (E)-3-(4-methoxyphenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl )-2-propen-1-ketone (abbreviation compound 3) preparation

[0034] Compound 3 was synthesized according to the preparation method of compound 1, the starting material was 2.23 g of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (0.01mol), p-methoxybenzaldehyde 1.36g (0.01mol), the product obtained is light yellow solid 2.60g, which is compound 3, yield: 76.8%; m.p.144~145°C; UV-vis (CH 3 OH)λ max : 343nm; IR (KBr): 3055.8 (Ar-H, =C-H), 2966.1, 2839.5 (CH 3 ), 1660.5 (C=O), 1606.1, 1507.3, 1460.2 (aromatic ring skeleton, C=C), 833.4 (=C-H) cm -1 ; 1 H NMR (300MHz, CDCl 3 )δ: 8.10 (d, 2H, triazole-H), 6.74~7.57 (m, 8H, Ar-H, C=CH), 3.73 (s, 3H, OCH 3 ) ppm; 13 C NMR (300MHz, CDCl 3 )δ: 187.1 (C=O), 163.3, 162.8, 158.7, 153.0, 145.3, 142.8, 133.3, 132.9, 131.9, 131.0, 123.3, 122.4, 114.8, 114.1, 112.4, 104.8 (Ar-C, triazole-C, C=CH), 55.5 (OCH 3 )ppm; MS (m / z): 342[M] + ...

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Abstract

The invention discloses novel triazoles compounds, whose chemical names are 3-(substituted phenyl)-1-(2,4-difluorophenyl)-2-(1,2,4-triazol-1-yl)-2-propen-1-one, 1-[3-(substituted phenyl)-1-(2,4-difluorophenyl)-2-(1,2,4-triazol-1-yl)allyl]piperidinium, 3-(substituted phenyl)-1-(2,4-difluorophenyl)-2-(1,2,4-triazol-1-yl)-2-propen-1-ol, and 1-[3-(substituted phenyl)-1-(2,4-difluoropheny)-2-(1,2,4-triazol-1-yl)proyl]piperidinium, with antimicrobial activity; further discloses the preparation method and pharmaceutical use thereof.

Description

technical field [0001] The invention relates to novel triazole compounds with antimicrobial effect, in particular to triazolenone, triazolenol, triazole piperidinium compounds, preparation method and medical application. Background technique [0002] In recent years, with the widespread application of broad-spectrum antibiotics, hormones, and immunosuppressants, the spread of AIDS, and the popularization and application of organ transplantation and interventional techniques, the incidence of microbial infections such as fungi and bacteria has shown an upward trend, and infectious strains have also occurred. The reports of drug-resistant strains have gradually increased, and the treatment of fungal and bacterial infections is facing severe challenges. In order to solve the problem of drug resistance of fungi and bacteria, countries all over the world are vigorously strengthening the research and development of new drugs. In new drug research, triazole compounds have attracte...

Claims

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Application Information

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IPC IPC(8): C07D249/08A61K31/4196A61P31/00
Inventor 周成合吴俊金磊米佳丽张飞飞江扬
Owner SOUTHWEST UNIVERSITY
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