Design, synthesis and biological evaluation of novel mansonone E derivatives prepared via CuAAC click chemistry as topoisomerase II inhibitors

Huang, Zhihong; Zhuo, Shitian; Li, Chunyan; Xie, Hua-Ting; Li, Ding; Tan, Jia‐Heng; Ou, Tian‐Miao; Huang, Zhi‐Shu; Gu, Lian‐Quan; Huang, Shi‐Liang

doi:10.1016/j.ejmech.2013.07.011

Cited by 30 publications

(11 citation statements)

References 33 publications

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“…Different compounds containing 1,2,3-triazoles with interesting antiproliferative activity have been reported [16,17,18,19,20]. This has recently led us to investigate the synthesis and antiproliferative activity of different terpenes coupled to triazole rings by the click chemistry technique [21,22,23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives

et al. 2015

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Abstract:Abietane diterpenes exhibit an array of interesting biological activities, which have generated significant interest among the pharmacological community. Starting from the abietane diterpenes carnosic acid and carnosol, twenty four new triazole derivatives were synthesized using click chemistry. The compounds differ in the length of the linker and the substituent on the triazole moiety. The compounds were assessed as antiproliferative and antifungal agents. The antiproliferative activity was determined on normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells while the antifungal activity was assessed against Candida albicans ATCC 10231 and Cryptococcus neoformans ATCC 32264. The carnosic acid γ-lactone derivatives 1-3 were the most active antiproliferative compounds of the series, with IC50 values in the range of 43.4-46.9 μM and 39.2-48.9 μM for MRC-5 and AGS cells, respectively. Regarding antifungal activity, C. neoformans was the most sensitive fungus, with nine compounds inhibiting more than 50% of its fungal growth at concentrations ≤250 µg·mL In turn, six compounds inhibited 50% C. albicans growth at concentrations lower than 250 µg·mL −1 .

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives

et al. 2015

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“…Inspired by these findings, Huang et al equipped the ME backbone with a C-3 triazole unit as well as C-9 halogenated substituents (Cl or Br). The resulting ME derivatives 77 produced comparable or even better antitumor efficacies toward the tumor lines A549, HL-60, K562, and Hela, as summarized in Figure …”

Section: Strategies To Identify and Develop Chemical Agents Targeting...mentioning

confidence: 99%

Discovery of Novel Topoisomerase II Inhibitors by Medicinal Chemistry Approaches

Huang

et al. 2018

J. Med. Chem.

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DNA topoisomerase II (topo II) is an important enzyme involved in DNA replication, recombination, and repair. Despite the popular applications of topo II inhibitors in cancer therapy, there is still an urgent need to upgrade topo II inhibitors to cope with drug resistance and severe adverse effects. Accordingly, novel topo II catalytic or multitarget topo II inhibitors are gaining more attention and make it possible to ease the toxic limitations of topo II poisons. In this review, medicinal chemistry approaches are mainly discussed toward the development of potent topo II inhibitors with low toxicities.

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“…The result indicated that these compounds ( 3a – 3d , Figure 2 ) have the potential to be antitumor agents as topoisomerase II inhibitors. 19 …”

Section: Topoisomerase II Inhibitorsmentioning

confidence: 99%

The application of click chemistry in the synthesis of agents with anticancer activity

Wang¹,

Zhao²,

Ye³

et al. 2015

DDDT

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The copper(I)-catalyzed 1,3-dipolar cycloaddition between alkynes and azides (click chemistry) to form 1,2,3-triazoles is the most popular reaction due to its reliability, specificity, and biocompatibility. This reaction has the potential to shorten procedures, and render more efficient lead identification and optimization procedures in medicinal chemistry, which is a powerful modular synthetic approach toward the assembly of new molecular entities and has been applied in anticancer drugs discovery increasingly. The present review focuses mainly on the applications of this reaction in the field of synthesis of agents with anticancer activity, which are divided into four groups: topoisomerase II inhibitors, histone deacetylase inhibitors, protein tyrosine kinase inhibitors, and antimicrotubule agents.

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Design, synthesis and biological evaluation of novel mansonone E derivatives prepared via CuAAC click chemistry as topoisomerase II inhibitors

Cited by 30 publications

References 33 publications

Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives

Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives

Discovery of Novel Topoisomerase II Inhibitors by Medicinal Chemistry Approaches

The application of click chemistry in the synthesis of agents with anticancer activity

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