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Synthesis, Structure, and Antitumor Activities of Dehydroepiandrosteronyl Derivatives with 1,2,3-Triazoles

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Abstract

Objective: Dehydroepiandrosterone plays an important role in the human beings due to its ability to be converted into androgens and oestrogens. The aim of this paper is to synthesize a series of novel dehydroepiandrosteronyl 1,2,3-triazole derivatives and study the antitumor activity of the synthesized compounds. Methods: Novel dehydroepiandrosteronyl 1,2,3-triazole derivatives were synthesized across the Mitsunobu and click reaction, respectively. The cytotoxicities of the synthesized compounds against HeLa, HGC-27, and HEK-293T cells were determined by MTT assay. Results and Discussion: The results showed that compound (V) (3R,8R,9S,10R,13S,14S)3-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro17H-cyclopenta[a]phenanthren-17-one had better inhibitory activity against the tumor cell lines tested. The IC50 value of inhibitory activity on human cervical cancer cell (HeLa) and human gastric cancer cell (HGC-27) was 33.6 and 22.3 μmolL–1, respectively. Conclusions: This work provides useful strategies for the design and synthesis of new steroidal antitumor drugs. The synthesized compounds have certain inhibitory activity on tumor cell growth and proliferation, but have little damage on normal cells, which deserves further study.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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Funding

The work was financially supported by Key scientific and technological projects in Henan Province (232102310388 and 222102310480), the Key Projects of Henan Provincial High School (20B150029, 20B150028 and 23A350014) and the foundation of postdoctoral project start-up (210001 and 210003), and research start-up (22037 and 22047) of Zhengzhou University of Technology.

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Authors and Affiliations

  1. College of Chemical Engineering and Food Technology, Zhengzhou University of Technology, Zhengzhou, 450000, Henan, China

    Yong Wang, Wei Wang, Yu-Fei Wang, Cong-Jun Liu, Wen-Hua Su & **g-**g Li

  2. Postdoctoral Innovation Practice Base, Zhengzhou Institute of Technology, Zhengzhou, 450000, Henan, China

    Yong Wang & Wei Wang

  3. Henan Ground Biological Science and Technology Co., Ltd., Zhengzhou, 450000, Henan, China

    Tian-Zeng Gao

  4. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai, China

    Wei-Shi Li

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  1. Yong Wang
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Contributions

The author YW—conceptualization, data curation, and editing. The author WW—data curation, prepared the article and the samples and analyzed data in this work. The author YW—supervised the project. The authors C-JL, W-HS–investigation, data curation. The author T-ZG—project administration. The author J-JL—supervised the project. The author W-SL—project administration, supervision, and editing.

The authors YW and WW contributed equally to the article.

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Correspondence to Yong Wang or Wei Wang.

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Wang, Y., Wang, W., Wang, YF. et al. Synthesis, Structure, and Antitumor Activities of Dehydroepiandrosteronyl Derivatives with 1,2,3-Triazoles. Russ J Bioorg Chem 50, 982–990 (2024). https://doi.org/10.1134/S1068162024120343

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