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<p>Anthranylhydrazide derivatives were synthesized as potential 4-hydroxyalkenals scavengers. The syntheses were achieved from diversely substituted isatoic anhydride <b>1a</b>-<b>1c</b> by reaction of methylhydrazine leading to the methyl hydrazide derivatives <b>Ia</b>-<b>Ic</b>. Studies of the scavenging activity with 4-hydroxyhexenal (4-HHE) were conducted either in organic or aqueous media using TLC or <sup>1</sup>H NMR monitoring. Compounds <b>Ia</b> and <b>Ib</b> were found to be able to form, without any catalysis, stable acylhydrazone adducts which were fully characterized. Compound <b>Ib</b> displayed the best scavenging activity towards 4-HHE with faster reactions in both organic and aqueous media. The stability of the adduct <b>IIb</b> could be assessed in aqueous media. This activity was also further discussed with the help of computer assisted conformational analysis which allowed to characterize stable conformations of <b>IIa</b> and <b>IIb</b> with NH/π interactions.</p><p></p>

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Anthranylhydrazide as simple, easily accessible and effective scaffold for scavenging 4-hydroxynonenal and 4-hydroxyhexenal in vitro

  • 期刊论文

  • 发表日期：

    2025年10月30日

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  • Lucie Grand,
  • Thibaut Barbier,
  • Yves Queneau,
  • Laurent Soulère

摘要

Anthranylhydrazide derivatives were synthesized as potential 4-hydroxyalkenals scavengers. The syntheses were achieved from diversely substituted isatoic anhydride 1a-1c by reaction of methylhydrazine leading to the methyl hydrazide derivatives Ia-Ic. Studies of the scavenging activity with 4-hydroxyhexenal (4-HHE) were conducted either in organic or aqueous media using TLC or 1H NMR monitoring. Compounds Ia and Ib were found to be able to form, without any catalysis, stable acylhydrazone adducts which were fully characterized. Compound Ib displayed the best scavenging activity towards 4-HHE with faster reactions in both organic and aqueous media. The stability of the adduct IIb could be assessed in aqueous media. This activity was also further discussed with the help of computer assisted conformational analysis which allowed to characterize stable conformations of IIa and IIb with NH/π interactions.