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Antifungal compound of alkyl substitutional triazole class

A technology of triazoles and antifungal, which is applied in the field of medicine and can solve the problems of increased difficulty in synthesis

Inactive Publication Date: 2006-04-19
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with fluconazole, vigorconazole and lavconazole and other second-generation triazole alcohol compounds currently in clinical use or under research have a broad antibacterial spectrum, and their antibacterial activity against Aspergillus fungi is significantly enhanced. Azole is comparable and effective against fluconazole-resistant strains. Its structural feature is that a methyl group is added at the 3-position, a chiral carbon atom is added, and the difficulty of synthesis is significantly increased.

Method used

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  • Antifungal compound of alkyl substitutional triazole class
  • Antifungal compound of alkyl substitutional triazole class
  • Antifungal compound of alkyl substitutional triazole class

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Synthesis of 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-3-(2-pyridylmercapto)-2-propanol

[0079] Take 1.78g (16mmol) 2-mercaptopyridine, 4.15g (15mmol) 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-2,3-epoxypropylene methanesulfonate salt and 5.52g (40mmol) of potassium carbonate were put into a 100ml three-necked flask, then a little tetrabutylammonium bromide and 55ml DMF were added, stirred and reacted at 75°C for 8h, filtered, and the filtrate was adjusted to pH=2 with hydrochloric acid, ethyl acetate The ester was washed (30ml×3), the water phase was adjusted to pH=10 with 10% sodium hydroxide, the solid was filtered out, and recrystallized with absolute ethanol to obtain 1.4g of light yellow powder, yield 31.96%, mp: 68-70°C .

[0080] 1 H-NMR (DMSO-d 6 )δ, ppm: 8.44 (1H, s, triazole C 3 -H), 7.91 (1H, s, triazole C 5 -H), 8.32 (1H, d, pyridine-C 6 -H), 7.62 (1H, m, pyridine-C 4 -H), 7.28 (1H, d, pyridine-C 3 -H), 7.12 (1H, m, pyridine-C 5 -H), 5.50 (1H, s, OH), 4....

Embodiment 2

[0083] 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-3-[4-(4-methoxyphenyl)piperazin-1-yl]-2-propane Alcohol synthesis

[0084] Add 1.39g (5mmol) 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-2,3-epoxypropylene methanesulfonate successively in a 100ml three-necked flask, 0.96g (5mmol) 1-[4-(4-methoxy)phenyl]piperazine, 1.38g (10mmol) potassium carbonate, a little cetyltrimethylammonium bromide and 30ml absolute ethanol, at 90 Heat and stir in a water bath at ℃ for 7 hours, pour into 100ml of water, extract with ethyl acetate (30ml×3), wash with water, dry over anhydrous sodium sulfate, recover the solvent to obtain a solid, recrystallize with ethyl acetate to obtain 0.83g of white needle crystals , Yield: 55.63%, mp: 110-111°C.

[0085] 1 H-NMR (DMSO-d 6 )δ, ppm: 7.94, 8.48 (2H, s, s, triazole-H), 6.77~6.84 (4H, m, Ar-H), 4.53 (1H, s, OH), 4.32 (2H, s, -CH 2 -), 3.67 (3H, s, -OCH 3 ), 2.29-2.88 (10H, m, piperazine-H,-CH 2 -), 0.91(9H, s, -C(CH 3 ) 3 )

[0086] IR (cm -1 , KBr): 3...

Embodiment 3

[0088] 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-3-[4-(4-ethoxyphenyl)piperazin-1-yl]-2-propane Alcohol synthesis

[0089] Add 1.39g (5mmol) 1-(1H-1,2,4-triazol-1-yl)-2-tert-butyl-2,3-epoxypropylene methanesulfonate successively in a 100ml three-necked flask, 1.03g (5mmol) 1-[4-(4-ethoxy)phenyl]piperazine, 1.38g (10mmol) potassium carbonate, a little cetyltrimethylammonium bromide and 30ml absolute ethanol, according to implementation According to the operation steps of Example 2, 1.17 g of white crystals were obtained, yield: 60.5%, mp: 78-80°C.

[0090] 1 H-NMR (DMSO-d 6 )δ, ppm: 7.94, 848 (2H, s, s, triazole-H), 6.76~6.82 (4H, m, Ar-H), 4.52 (1H, s, OH), 4.32 (2H, s, -CH 2 -), 3.93 (2H, q, J=7.0Hz, -OCH 2 -), 2.27-2.88 (10H, m, piperazine-H, -CH 2 -), 1.28 (3H, t, J=70Hz, -CH 3 ), 0.91 (9H, s, -C (CH 3 ) 3 )

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Abstract

An alkyl substituted triazazole type antifungal compound for preparing the antifungal medicines, and its various enantiomers, diaisomers, Nox and precursors are disclosed.

Description

technical field [0001] The invention relates to the field of medical technology, and is a novel alkyl triazole antifungal compound, in which 2,4-difluorophenyl in the molecule of common azole antifungal compounds is replaced by an alkyl group: 1-(1H-1 , 2,4-triazol-1-yl)-2-alkyl-3-substituted-2-propanol. Background technique [0002] In recent years, with the extensive use of antibiotics, the increase in the number of cancer patients undergoing chemotherapy and organ transplantation, the widespread use of catheters and intubations, the widespread use of corticosteroids and immunosuppressants, and the prevalence of immunodeficiency patients, especially AIDS patients, Rapid increase, resulting in a sharp increase in the incidence of fungal infections, especially deep fungal infections. Deep fungal infection has risen to the third largest infectious disease clinically, seriously threatening human health. Statistics show that 60% of the direct cause of death among AIDS patient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/02C07D403/06C07D403/08C07D403/12C07D405/02C07D405/06C07D405/08C07D405/12A61P31/10
Inventor 刘超美何秋琴门秀峰曹永兵董玉环赵荔华姜远英赵靖霞
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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