Synthesis and antitumor effects of a new class of 1,2,4-triazole derivatives
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02652-y
ORIGINAL RESEARCH
Synthesis and antitumor effects of a new class of 1,2,4-triazole derivatives Zheng Wu1 Xin Li1 Chun-Lan Chi1 Lu Xu1 Yong-Yue Sun1 Bao-Quan Chen1 ●
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Received: 4 June 2020 / Accepted: 8 October 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract In order to obtain more effective antitumor agents, a new class of 1,2,4-triazole derivatives bearing disulfide bond were designed and synthesized. All the final compounds were confirmed by IR, 1H NMR, 13C NMR and HR-ESI-MS. The in vitro cytotoxicity of the compounds on the SMMC-7721, Hela, A549 cancer cell lines and the L929 normal cell lines were assessed by cell counting kit-8 (CCK-8). Many of tested compounds 8a–h, 9a–h, 10a–h had better cytotoxic activity on various cancer cell lines than positive control 5-fluorouracil, and they were less cytotoxic to normal cell line L929 than cancer cells. Among them, compounds 9e, 9g, and 10h showed better cytotoxic activity on SMMC-7721 cells with IC50 values 4.12, 2.92, and 4.53 μM, respectively. Compounds 8a, 9g, 10g and 10h displayed high antiproliferative activity against Hela cells with IC50 values 6.31, 4.31, 6.31 and 3.97 μM, respectively. Compounds 8c, 10a and 10h revealed effective biological potency on A549 cells with IC50 values 4.75, 4.92 and 3.73 μM, respectively. Moreover, a great majority of tested compounds revealed low cytotoxicity on normal cell line L929. Keywords 1,2,4-Triazole Disulfides Synthesis Antiproliferative activity Cytotoxicity ●
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Introduction Cancer is a disease with high mortality characterized by abnormal cell proliferation and spread, and has become a disease that needs to be solved urgently [1]. Therefore, designing and synthesizing new anticancer drugs with high efficiency and selectivity has important modern significance [2]. Five-membered heterocyclic compounds, such as 1,3,4oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazoles, have been found to possess a wide array of biological properties
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02652-y) contains supplementary material, which is available to authorized users. * Yong-Yue Sun [email protected] * Bao-Quan Chen [email protected] 1
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China
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and been a most referenced building blocks in the field of pharmaceutical research [3–7]. Particularly, further literature survey revealed that 1,2,4-triazoles and their fused heterocyclic derivatives have expressed a high level of selectivity with versatile biological activities, such as antioxidant [3, 8, 9], anticonvulsant [10, 11], anticancer [12, 13], antibacterial [14–19], anti-inflammatory [20–23], analgesic [24, 25], antifungal [26], antitubercular
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