Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents

被引：110

作者：

Fakhr, Issa M. I. ^{[1
]}

Radwan, Mohamed A. A. ^{[1
]}

El-Batran, Seham ^{[2
]}

El-Salam, Omar M. E. Abd ^{[2
]}

El-Shenawy, Siham M. ^{[2
]}

机构：

[1] Natl Res Ctr, Appl Organ Chem Dept, Cairo, Egypt

[2] Natl Res Ctr, Dept Pharmacol, Cairo, Egypt

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 04期

关键词：

Zileuton; Benzo[b]thiophene; Anti-inflammatory and analgesic; SOLID-PHASE SYNTHESIS; DIRECTED THROMBIN INHIBITORS; FACTOR XA; DERIVATIVES; MODULATORS; ASSAY;

D O I：

10.1016/j.ejmech.2008.02.034

中图分类号：

R914 [药物化学];

学科分类号：

100705 [微生物与生化药学];

摘要：

An efficient method for trapping isocyanate 4, generated from the Curtius rearrangement, with ethyl alcohol to afford the carbamate 5 is reported. 5-Nitrobenzo[b]thiophene-2-carboxylic acid 1 is converted to the corresponding hydrazide 2 by the reaction with hydrazine hydrate and then to the azide 3 with nitrous acid, followed by thermal rearrangement, cooling, and trapping in one pot reaction. The carbamate 5 is treated with hydrazine hydrate to afford the desired, Zileuton analogue, 4-(5-nitrobenzo[b]thiophene-2-yl)semicarbazide 6. Also the reactivity of hydrazide 2 towards some carboxyaldehydes and phenylisothiocyanate afforded the corresponding carbohydrazides 7, 8 and phenylthiosemicarbazide 9, respectively. Compounds 9, 2 and 6, respectively, were more potent as anti-inflammatory and anti - noci ceptive agents. (c) 2008 Elsevier Masson SAS. All rights reserved.

引用

页码：1718 / 1725

页数：8

共 24 条

[1]

REVISED ASSAY FOR SERUM PHENYL PHOSPHATASE-ACTIVITY USING 4-AMINO-ANTIPYRINE [J].