Syntheses, cytotoxic activity evaluation and HQSAR study of 1,2,3-triazole-linked isosteviol derivatives as potential anticancer agents

Liu, Cong-Jun; Liu, Yan-Ping; Yu, Shuling; Dai, Xing‐Jie; Zhang, Tao; Tao, Jing‐Chao

doi:10.1016/j.bmcl.2016.10.028

Cited by 19 publications

(10 citation statements)

References 31 publications

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“…Liu et al. 73 designed and synthesised a series of novel 1,2,3-triazole-linked isosteviol derivatives using the Huisgenclick reaction. The cytotoxicities of these compounds against HCT-116 and JEKO-1 cells were screened in vitro .…”

Section: Biological Activitiesmentioning

confidence: 99%

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Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Nature products have been extensively used in the discovery and development of new drugs, as the most important source of drugs. The triazole ring is one of main pharmacophore of the nitrogen-containing heterocycles. Thus, a new class of triazole-containing natural product conjugates has been synthesised. These compounds reportedly exert anticancer, anti-inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, anti-Alzheimer, and enzyme inhibitory effects. This review summarises the research progress of triazole-containing natural product derivatives involved in medicinal chemistry in the past six years. This review provides insights and perspectives that will help scientists in the fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology.

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Section: Biological Activitiesmentioning

confidence: 99%

“…Derivatives of isosteviol-triazole not only possess anti-colon cancer activity 73 , but also they exhibit anti-multiple cancer cell activity 98 . Compounds with different phenyl 1,2,3-triazole chloroacetamide showed considerably higher antiproliferative activity against the HCT-116 and HepG2 cell lines.…”

Section: Biological Activitiesmentioning

confidence: 99%

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Isosteviol is a tetracyclic ent-beyerane diterpene that is endowed with multifarious bioactivities and can be readily isolated from stevia plant. (Liu et al, 2016). Quan et al reported that C19 isosteviol-triazole D8 could inhibit the growth of several cancer cell lines and HepG2) with IC 50 values in the range of 5.38-15.91 μM, and that was 1.3-to 4.6-fold more potent than the reference drug 5fluorouracil, and 6.3-to 16.8-fold more potent than the parental isosteviol (Luan et al, 2019).…”

Section: Click Chemistriesmentioning

confidence: 99%

Click Chemistry in Natural Product Modification

Zhang

Zhao

et al. 2021

Front. Chem.

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Click chemistry is perhaps the most powerful synthetic toolbox that can efficiently access the molecular diversity and unique functions of complex natural products up to now. It enables the ready synthesis of diverse sets of natural product derivatives either for the optimization of their drawbacks or for the construction of natural product-like drug screening libraries. This paper showcases the state-of-the-art development of click chemistry in natural product modification and summarizes the pharmacological activities of the active derivatives as well as the mechanism of action. The aim of this paper is to gain a deep understanding of the fruitful achievements and to provide perspectives, trends, and directions regarding further research in natural product medicinal chemistry.

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“…Furthermore, the cytotoxic activities of isosteviol derivatives have attracted much attention in recent years. In the previous study, the C-15 and C-16 functionalized isosteviol derivatives, obtained by means of group-conversion or structural modification exhibited good cytotoxic activities [17,18,19,20,21,22,23,24]. In view of the low cytotoxicity of isosteviol, it is suitable for the development of highly selective anticancer drugs by chemical modification [14,15,16].…”

Section: Introductionmentioning

confidence: 99%

“…Our previous study investigated the structure-activity relationship of the antiproliferative effects of celastrol analogues. Compound C which has a tryptophan methyl ester introduced in the 20th carboxylic acid position, inhibited cell proliferation of AGS cells with an IC 50 value of 0.44 μM [23]. Similarly, a drug with a phosphonate introduced can display enhanced solubility and drug-like properties by regulating the distribution coefficient.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

et al. 2018

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Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. Most of the derivatives tested here exhibited improved antiproliferative activity with high selectivity when compared with the parent compound isosteviol and the positive control drug 5-fluorouracil. Among these derivatives; compound 5d exhibited the most potent antiproliferative activity and commendable selectivity between cancer and normal cells. In addition; compound 5d inhibited the colony formation of HCT-116 cells in a concentration-dependent manner. Further studies revealed that compound 5d arrested the HCT-116 cell cycle in the S phase; and western blot analysis demonstrated the mechanism may be correlated with a change in the expression of cyclin A; cyclin B1; and cyclin E1. Furthermore; the results of a docking study that involved placing compound 5d into the CDK2/cyclin A binding site revealed that its mode of action was possibly as a CDK2/cyclin A inhibitor.

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Syntheses, cytotoxic activity evaluation and HQSAR study of 1,2,3-triazole-linked isosteviol derivatives as potential anticancer agents

Cited by 19 publications

References 31 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Click Chemistry in Natural Product Modification

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

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