1,3-二烯丙烯衍生物o -丙炔基- n -乙酰吡唑的合成及其抗炎活性

A. Dhingra, B. Chopra, R. Dass, S. K. Mittal
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引用次数: 4

摘要

为了寻找新型有效的口服炎症治疗药物,以丙炔溴为原料,对1,3-二烯丙烯(3a-j)衍生的n -乙酰吡唑(4a-j)进行处理,制备了新型的o -丙炔基- n -乙酰吡唑类似物(5a-j)。一系列取代芳基酮1和苯甲醛2在冰醋酸中Claisen-Schmidt缩合得到1,3-二芳基丙烯,在乙酸回流条件下用水合肼进一步处理得到1-乙酰-3,5-二芳基-4,5-二氢(1H)吡唑(4a-j)。利用红外、核磁共振等光谱技术对产物进行了表征。此外,采用角叉菜胶诱导大鼠足跖水肿法测定合成化合物的体内抗炎活性。
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Synthesis and Anti-Inflammatory Activity of Some O-Propargylated-N-acetylpyrazole Derived from 1,3-Diarylpropenones
In search of novel effective potent therapeutic agents delivered by oral route for inflammation treatment, some novel O-propargylated-N-acetylpyrazole analogs (5a–j) were prepared by treating N-acetylpyrazole (4a–j) derived from 1,3-diarylpropenones (3a–j) with propargyl bromide. Claisen-Schmidt condensation of a series of substituted aryl ketones 1 and benzaldehydes 2 in glacial acetic acid afforded 1,3-diarylpropenones which on further treatment with hydrazine hydrate in acetic acid under reflux conditions afforded 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles (4a–j). The products were characterized by using spectroscopic techniques such as IR and NMR. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenan-induced paw oedema method in rats.
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期刊介绍: International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis. International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis.
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