Scholarlink

<p>In this study, new cinnamic acid linked to triazole acetamide derivatives was synthesized and evaluated for anti-Alzheimer and anti-melanogenesis activities. The structural elucidation of all analogs was performed using different analytical techniques, including <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, mass spectrometry, and IR spectroscopy. The synthesized compounds were assessed in vitro for their inhibitory activities against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase enzymes. Among synthesize derivative compound 3-(4-((1-(2-((2,4-dichlorophenyl)amino)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)acrylic acid (<b>10j)</b> exhibited the highest activity against BChE with an IC<sub>50</sub> value of 11.99 ± 0.53 µM. Derivative 3-(3-methoxy-4-((1-(2-oxo-2-(p-tolylamino)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acrylic acid (<b>10d)</b>, bearing a 4-CH<sub>3</sub> group, was identified as the most potent AChE inhibitor. In terms of tyrosinase inhibition, 3-(3-methoxy-4-((1-(2-((2-methyl-4-nitrophenyl)amino)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acrylic acid (compound <b>10n)</b>, demonstrated 44.87% inhibition at a concentration of 40 µM. Additionally, a kinetic study of compound <b>10j</b> which 2,4-dichlorophenyl substituents against BChE revealed a mixed-type inhibition pattern. Furthermore, molecular docking and molecular dynamic studies of compound <b>10j</b> were conducted to thoroughly evaluate its mode of action within the BChE active site.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Cinnamic acid conjugated with triazole acetamides as anti-Alzheimer and anti-melanogenesis candidates: an in vitro and in silico study

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年1月3日

查看全文
  • Amir Shervin Shokouhi Asl,
  • Mohammad Hosein Sayahi,
  • Mohammad Hashem Hashempur,
  • Cambyz Irajie,
  • Amir Hossein Alaeddini,
  • Seyedeh Niloufar Ghafouri,
  • Milad Noori,
  • Navid Dastyafteh,
  • Javad Mottaghipisheh,
  • Mehdi Asadi,
  • Bagher Larijani,
  • Mohammad Mahdavi,
  • Aida Iraji

摘要

In this study, new cinnamic acid linked to triazole acetamide derivatives was synthesized and evaluated for anti-Alzheimer and anti-melanogenesis activities. The structural elucidation of all analogs was performed using different analytical techniques, including 1H-NMR, 13C-NMR, mass spectrometry, and IR spectroscopy. The synthesized compounds were assessed in vitro for their inhibitory activities against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase enzymes. Among synthesize derivative compound 3-(4-((1-(2-((2,4-dichlorophenyl)amino)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)acrylic acid (10j) exhibited the highest activity against BChE with an IC50 value of 11.99 ± 0.53 µM. Derivative 3-(3-methoxy-4-((1-(2-oxo-2-(p-tolylamino)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acrylic acid (10d), bearing a 4-CH3 group, was identified as the most potent AChE inhibitor. In terms of tyrosinase inhibition, 3-(3-methoxy-4-((1-(2-((2-methyl-4-nitrophenyl)amino)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)acrylic acid (compound 10n), demonstrated 44.87% inhibition at a concentration of 40 µM. Additionally, a kinetic study of compound 10j which 2,4-dichlorophenyl substituents against BChE revealed a mixed-type inhibition pattern. Furthermore, molecular docking and molecular dynamic studies of compound 10j were conducted to thoroughly evaluate its mode of action within the BChE active site.