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Abstract <p><b>Objective:</b> Dehydroabietic acid (DHAA) is an important natural triterpene resin acid with a wide range of pharmacological activities, including antibacterial, antifungal, antiviral, and anti-inflammatory effects, particularly in antitumor activity. The aim of this study was to synthesize a series of novel dehydroabietic acid 1,2,3-triazole derivatives and evaluate their antitumor activity. <b>Methods:</b> Click chemistry was employed to conjugate dehydroabietic acid (DHAA) with 1,2,3-triazole, yielding 12 DHAA derivatives containing 1,2,3-triazole with yields ranging from 64.5 to 90%. The structures of the target compounds were confirmed by <sup>1</sup>H, <sup>13</sup>C NMR, and HR-MS (ESI). The initial antiproliferative activity of these compounds was assessed <i>in vitro</i> using two tumor cell lines (human cervical cancer cells, HeLa, and human breast carcinoma cells, MCF-7), with cisplatin used as a reference. <b>Results and Discussion:</b> The results indicated that three compounds, <b>VII</b>, <b>VIII</b>, and <b>IX</b>, exhibited significant antiproliferative activity against the tumor cell lines. Among them, compound <b>VIII</b> (4-(4-fluorophenyl)-1-(((1<i>R</i>,4a<i>S</i>)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-1<i>H</i>-1,2,3-triazole) demonstrated particularly remarkable activity, with an IC<sub>50</sub> value of 22.1 μM against HeLa cells and 23.2 μM against MCF-7 cells. <b>Conclusions:</b> This study provides useful strategies for the design and synthesis of novel antitumor agents. The synthesized compounds exhibit some inhibitory effects on tumor cell growth and proliferation while causing minimal damage to normal cells, warranting further investigation.</p>

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Synthesis of Dehydroabietic Acid Derivatives with 1,2,3-Triazole Substituents and Their Antiproliferative Activity against HeLa, MCF-7, and HEK-293T Cells

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • Yong Wang,
  • Li-Na Liu,
  • Shang-Hua Wei,
  • Wei Wang,
  • Cong-Jun Liu,
  • Song Gao,
  • Shu-Ping Yu,
  • Ning Yao,
  • Yu-Fei Wang

摘要

Abstract

Objective: Dehydroabietic acid (DHAA) is an important natural triterpene resin acid with a wide range of pharmacological activities, including antibacterial, antifungal, antiviral, and anti-inflammatory effects, particularly in antitumor activity. The aim of this study was to synthesize a series of novel dehydroabietic acid 1,2,3-triazole derivatives and evaluate their antitumor activity. Methods: Click chemistry was employed to conjugate dehydroabietic acid (DHAA) with 1,2,3-triazole, yielding 12 DHAA derivatives containing 1,2,3-triazole with yields ranging from 64.5 to 90%. The structures of the target compounds were confirmed by 1H, 13C NMR, and HR-MS (ESI). The initial antiproliferative activity of these compounds was assessed in vitro using two tumor cell lines (human cervical cancer cells, HeLa, and human breast carcinoma cells, MCF-7), with cisplatin used as a reference. Results and Discussion: The results indicated that three compounds, VII, VIII, and IX, exhibited significant antiproliferative activity against the tumor cell lines. Among them, compound VIII (4-(4-fluorophenyl)-1-(((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-1H-1,2,3-triazole) demonstrated particularly remarkable activity, with an IC50 value of 22.1 μM against HeLa cells and 23.2 μM against MCF-7 cells. Conclusions: This study provides useful strategies for the design and synthesis of novel antitumor agents. The synthesized compounds exhibit some inhibitory effects on tumor cell growth and proliferation while causing minimal damage to normal cells, warranting further investigation.