N-酰基-N′-(2-吲哚甲酰基)肼的合成及其生理活性

SYNTHESIS OF DIACYLHYDRAZIDES OF 2-INDOLE AND THEIR PHYSIOLOGICAL ACTIVITY

摘要: 2-吲哚甲酰肼与取代基为H,CH₃,ClCH₂,C₂H₅,CH₃(CH₂)₃,4-Br-C₆H₄和3-吡啶基的甲酰氯在DMF中反应时均得双酰肼化合物。但在乙腈中与乙酰氯或丙酰氯反应时,分别得到两种失水产物,经¹³C核磁共振仪分析表明其为吲哚2位(口恶)二唑取代的化合物,其余仍为双酰肼化合物。体外试验显示;N-甲酰基,N-氯代乙酰基-2-吲哚甲酰肼(Ⅰ,Ⅲ)和2-2-(5-乙基)-1,3,4-(口恶)二唑-吲哚(Ⅸ)对强毒人型结核菌H₃₇RV有抑制作用。

Abstract: Several diacyl (aroyl) hydrazides of 2-indole were synthesised by the reaction of 2-indolecarboxylic acid hydrazides with acyl (aroyl) chlorides (RCOCl or ArCOC1, R=H, CH₃, C₂H₅, CICH₂, CH₃(CH₂)₃, and Ar=4-Br-C₆H₄-or 3-C₅H₄N-) in anhydrous DMF or acetonitrile. It was found that when 2-indolecarboxylic acid hydrazide reacted with acetyl or propionyl chloride in acetonitrile, two other compounds were isolated. Their structures were established by ¹³C NMR spectroscopy.Formyl and acetylhydrazide of 2-indolecarboxylic acid and 2--5-(2-ethyl)-1,3,4oxadiazole-indole were shown to have bacteriostatic activity in vitro on Mycobacterium tuberculosis (Zopf.) Lehmann et Neumann.