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Benzene acylated 1,5-diaryl-1,2,4-triazole derivative, its preparation method and medical use

A technology of phenylacryloyl and acryloylation, which is applied in the production of bulk chemicals, drug combination, anti-tumor drugs, etc., can solve the problems that 5-LOX has no obvious inhibitory effect and no anti-tumor activity.

Inactive Publication Date: 2017-10-24
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of compound has no obvious inhibitory effect on 5-LOX and has no antitumor activity

Method used

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  • Benzene acylated 1,5-diaryl-1,2,4-triazole derivative, its preparation method and medical use
  • Benzene acylated 1,5-diaryl-1,2,4-triazole derivative, its preparation method and medical use
  • Benzene acylated 1,5-diaryl-1,2,4-triazole derivative, its preparation method and medical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193] Preparation of 1-(4-bromophenyl)-3-thiosemicarbazide

[0194] Suspend p-bromophenylhydrazine hydrochloride (5.0g, 0.022mol) in 20mL of absolute ethanol, add 0.5mL of concentrated hydrochloric acid, raise the temperature to 40°C, add KSCN (2.6g, 0.027mol) in batches within 40min, and complete the addition , heated up to reflux for 10h, ended the reaction, filtered while it was hot, washed the filter cake with ethanol (3 × 5mL) and discarded; after most of the solvent was evaporated from the filtrate under reduced pressure, water was added to precipitate a large amount of precipitate, left to stand, filtered with suction, The filter cake was washed with ice water to obtain 2.5 g of dark red solid, yield: 45.6%. m.p.198-200℃; ESI-MSm / z: 245.8[M-H] - .

Embodiment 2

[0196] Preparation of 4-methylsulfonylbenzoyl chloride

[0197] p-Methanesulfonylbenzoic acid (10g, 0.050mol) was suspended in 50mL of dry dichloromethane, oxalyl chloride (15mL, 0.150mol) was added, catalyzed by adding 1 drop of DMF, stirred at room temperature for 3h, the reaction was stopped, and the reaction solution was Concentrate to dryness under reduced pressure to obtain 10.1 g of white solid, yield: 92.6%, m.p.131-133°C.

Embodiment 3

[0199] Preparation of 2-(4-methylsulfonylbenzoyl)-2-(4-bromophenyl)thiosemicarbazide

[0200] Dissolve 1-(4-bromophenyl)-3-thiosemicarbazide (0.83g, 3.4mmol) in 20mL of dry acetone, drop triethylamine 5d into it, stir at room temperature, add compound 1 in batches within 30min ( 0.74g, 3.4mmol), the reaction solution gradually became turbid, after the addition, the temperature was raised to reflux for 2h, the reaction was terminated, cooled, suction filtered, the filter cake was washed with acetone (3×5mL), and dried to obtain a white solid 1.05g, the yield : 72.6%. m.p.178-180℃; ESI-MS m / z: 427.9[M-H] - .

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PUM

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Abstract

The invention relates to a class of phenylacryloyl 1,5-diaryl-1,2,4-triazole derivatives, a preparation method and medical application thereof, and belongs to the field of medicinal chemistry. The results of pharmacological experiments show that these compounds have good cyclooxygenase-2 (COX-2) / 5-lipoxygenase (5-LOX) inhibitory activity and good anti-tumor activity, and can be used to prepare and treat tumors and Drugs for other diseases or conditions related to COX‑2 and 5‑LOX pathways.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new class of phenylacryloyl 1,5-diaryl-1,2,4-triazole derivatives and a preparation method thereof. The invention also discloses a pharmaceutical composition containing the compound and the compound is effective in treating tumors and other diseases by inhibiting the activities of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Use in Diseases or Conditions. Background technique [0002] In the middle of the 19th century, German pathologist Rudolf Vichow discovered leukocyte infiltration in malignant tumor tissue, and for the first time proposed that tumors may originate from chronic inflammation. Epidemiological studies have found that patients with chronic inflammation are more likely to develop secondary tumors, and up to 15% of tumor occurrence and development are related to inflammation caused by infection (Curr Urol Rep, 2008, 9(3): 243-249; Redox Rep, 2002 , 7(6...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12A61K31/4196A61P35/00
CPCY02P20/55
Inventor 徐进宜蔡浩徐盛涛吴晓明江波裘杨溢张朋飞沈昊姚和权谢唯佳
Owner CHINA PHARM UNIV
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