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<p></p><p>We have studied POCl<sub>3</sub>-catalyzed cyclodehydration reaction of 2-(4-chloro-2-oxoquinolin-1(2<i>H</i>)-yl)acetohydrazide with benzoic acids. Unusually, we have found that <i>p</i>-methyl-, <i>p</i>-methoxy-, <i>p</i>-chloro-substituted and unsubstituted benzoic acids failed to undergo cyclodehydration and were converted into the corresponding anhydrides. Whereas, <i>p</i>-nitrobenzoic acid successfully underwent cyclodehydration and yielded 1,3,4-oxadiazole. Trying the same reaction with 2-(4-methyl-2-oxoquinolin-1(2<i>H</i>)-yl)-acetohydrazide and <i>p</i>-nitrobenzoic acid, there was no cyclodehydration – two hydrazide molecules have condensed together. Newly synthesized 4-chloro-1-{[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methyl}quinolin-2(1<i>H</i>)-one and <i>N</i>'-[2-(4-methyl-2-oxoquinolin-1(2<i>H</i>)-yl)acetyl]-4-nitrobenzohydrazide were evaluated for their anticancer activity against human lung cancer cells A549.</p>

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Synthesis of 4-chloro-1-{[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methyl}quinolin-2(1H)-one and N'-[2-(4-methyl-2-oxoquinolin-1(2H)-yl)acetyl]-4-nitrobenzohydrazide using POCl3 and their cytotoxic activity against human lung cancer cells A549

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • Duraisamy Gunasekaran,
  • Devadoss Karthik Kumar

摘要

We have studied POCl3-catalyzed cyclodehydration reaction of 2-(4-chloro-2-oxoquinolin-1(2H)-yl)acetohydrazide with benzoic acids. Unusually, we have found that p-methyl-, p-methoxy-, p-chloro-substituted and unsubstituted benzoic acids failed to undergo cyclodehydration and were converted into the corresponding anhydrides. Whereas, p-nitrobenzoic acid successfully underwent cyclodehydration and yielded 1,3,4-oxadiazole. Trying the same reaction with 2-(4-methyl-2-oxoquinolin-1(2H)-yl)-acetohydrazide and p-nitrobenzoic acid, there was no cyclodehydration – two hydrazide molecules have condensed together. Newly synthesized 4-chloro-1-{[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methyl}quinolin-2(1H)-one and N'-[2-(4-methyl-2-oxoquinolin-1(2H)-yl)acetyl]-4-nitrobenzohydrazide were evaluated for their anticancer activity against human lung cancer cells A549.