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Triazole alcohol derivatives, and preparation method and application thereof

A triazole alcohol and pyrazole technology, applied in the field of pharmaceutical compounds, can solve the problems of easy drug resistance, narrow antibacterial spectrum, and inability to meet the needs of treatment, etc.

Inactive Publication Date: 2020-03-17
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

However, as far as the antifungal drugs currently in clinical use are concerned, there are problems such as large side effects, narrow antibacterial spectrum, and easy drug resistance. Effective antifungal drugs, especially anti-deep fungal drugs, are very scarce, which are far from meeting the needs of treatment.

Method used

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  • Triazole alcohol derivatives, and preparation method and application thereof
  • Triazole alcohol derivatives, and preparation method and application thereof
  • Triazole alcohol derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Embodiment 1: the synthesis of compound 8

[0096]

[0097] Step 1: Dissolve compound 1 (50mmol) and 4-iodopyrazole (compound 2, 50mmol) in DMF (150mL), add potassium carbonate (100mmol), react at 80°C for 4 hours, monitor the reaction by TLC, when After the reaction was complete, the system was cooled to room temperature, poured into ice water, stirred for 1 hour, and the precipitated solid was filtered and vacuum-dried at 50° C. to obtain compound 3 (15.5 g, yellow solid, yield 72%). 1 H NMR (300MHz, DMSO-d 6 )δ8.31(s,1H),7.76(d,J=4.3Hz,2H),7.41(s,1H),7.23-7.15(m,2H),6.91-6.86(m,1H),6.29(s ,1H),4.74-4.44(m,4H).

[0098]

[0099] Step 2: Dissolve compound 3 (40mmol) and methyl 4-ethynylbenzoate (compound 6, 40mmol) in NMP (140mL), add PdCl 2 (PPh 3 ) 2 (5%mmol), CuI (5%mmol) and DIEA (200mmol), under nitrogen protection, reacted for 6 hours at 60°C, TLC monitored the reaction, after the reaction was complete, poured into ice water, then extracted with ethyl ...

Embodiment 2

[0102] Embodiment 2: the synthesis of compound 10a

[0103]

[0104] Steps: Dissolve compound 8 (1mmol) and 9a (1mmol) in DMF (5mL), add PyBOP (1.1mmol) and DIEA (2mmol), react until complete at 50°C, pour into water, and then extract with ethyl acetate 3 times, the organic phase was washed twice with saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate, concentrated using a rotary evaporator, and purified by column chromatography to obtain the target product 10a.

Embodiment 3

[0105] Embodiment 3: the synthesis of compound 10b

[0106]

[0107] Steps: Dissolve compound 8 (1mmol) and 9b (1mmol) in DMF (5mL), add PyBOP (1.1mmol) and DIEA (2mmol), react until complete at 50°C, pour into water, and then extract with ethyl acetate 3 times, the organic phase was washed twice with saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate, concentrated using a rotary evaporator, and purified by column chromatography to obtain the target product 10b.

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PUM

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Abstract

The invention relates to triazole alcohol derivatives, and a preparation method and application thereof. The chemical structures of the derivatives are shown as a formula I shown in the specification,wherein R represents a structure shown in the specification or a structure shown in the specification; R1 and R2 may individually represent a hydrogen atom, alkyl, aryl, aralkyl, or cycloalkyl; substituents may be located at various positions of the benzene ring in a mono- or poly-substituted manner; the substituents and R3 are selected from: a) a halogen which is F or Cl, b) an electron withdrawing group which is cyano or trifluoromethyl, c) C1-C4 lower alkyl or halogen-substituted C1-C4 lower alkyl, and d) C1-C4 lower alkoxy or halogen-substituted C1-C4 lower alkoxy. The compounds of the invention have strong antifungal activity, have the advantages of low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal drugs.

Description

technical field [0001] The invention relates to the technical field of medical compounds, in particular to a novel triazole alcohol derivative, its preparation method and application. Background technique [0002] In recent years, with the extensive application of broad-spectrum antibiotics, antineoplastic drugs, and immunosuppressants, the widespread implementation of radiotherapy and organ transplantation, the widespread development of catheters and intubations, and the rapid increase in immunocompromised patients, especially AIDS patients, have resulted in Fungal infections, especially deep fungal infections, have risen sharply, and deep fungal infections have become the main cause of death from major diseases such as AIDS and tumors. However, as far as the antifungal drugs in clinical use are concerned, there are problems such as large side effects, narrow antibacterial spectrum, and easy drug resistance. Effective antifungal drugs, especially anti-deep fungal drugs, are...

Claims

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Application Information

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IPC IPC(8): C07D403/06A61P31/10
CPCC07D403/06A61P31/10
Inventor 张大志姜远英倪廷峻弘谢斐丁子超郝雨濛王瑞娜
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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