Design, synthesis and anticancer activity of novel nopinone-based thiosemicarbazone derivatives

Wang, Yunyun; Gu, Wen; Yu, Shan; Liu, Fei; Xu, Xu; Yang, Yiqin; Zhang, Qiangjian; Zhang, Yan; Kuang, Hongbo; Wang, Zhonglong; Wang, Shifa

doi:10.1016/j.bmcl.2017.04.024

Cited by 62 publications

(18 citation statements)

References 30 publications

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“…Thiosemicarbazones (TSCs) have attracted a great deal of attention for many years owing to their pharmacological utility as therapeutic agents and versatility as ligands allowing them to give rise to a great variety of coordination modes [11,12]. In particular, TSCs have been identified as promising antiproliferative agents against a variety of tumors through the inhibition of diverse molecular targets including ribonucleotide reductase (RNR) [11][12][13][14][15][16][17][18][19][20]. Among them, triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone, 3-AP), a potent RNR inhibitor, is an anticancer agent currently in clinical trials (Figure 1) [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and in vitro evaluation of new thiosemicarbazone derivatives as potential anticancer agents

Sever¹,

Çiftçi²,

Özdemır³

et al. 2018

jrp

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Thiosemicarbazones play a pivotal role as potential therapeutic agents for the management of lung cancer. 4-(4-Cyanophenyl)-1-[(5-arylfuran-2-yl)methylene]thiosemicarbazides (1-10) were obtained via the reaction of 4-(4cyanophenyl)thiosemicarbazide with 5-arylfurfurals. MTT assay was performed to assess their cytotoxic effects on A549 human lung adenocarcinoma and L929 mouse fibroblast cell lines. Compounds 1, 5, 6 and 7 were identified as the most effective anticancer agents on A549 cell line with IC50 values of 12.75±0.35 µg/mL, 4.30±0.61 µg/mL, 5.50±2.12 µg/mL and 5.90±0.57 µg/mL, respectively compared to cisplatin (IC50= 12.00±0.71 µg/mL). The IC50 values of these compounds for L929 cell line were higher than their IC50 values for A549 cell line indicating that their anticancer effects were selective. The apoptotic effects of these compounds were also analyzed based on Annexin V-PI binding capacities in flow cytometry. According to flow cytometric analyses, the early apoptotic effects of compounds 1, 5, 6 and 7 on A549 cell line were determined as 4.7, 5.1, 7.3 and 5.1%, whereas their late apoptotic effects were determined as 3.7, 2.0, 4.9 and 3.3%, respectively. Compound 6 showed more apoptotic activity than compounds 1, 5 and 7. According to these findings, compounds 5 and 6 stand out as promising anticancer agents for further in vitro and in vivo studies.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and in vitro evaluation of new thiosemicarbazone derivatives as potential anticancer agents

Sever¹,

Çiftçi²,

Özdemır³

et al. 2018

jrp

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“…The extensive and diversified biological and pharmacological applications of Schiff's base metal complexes of semicarbazone [6,7] and thiosemicarbazone [8] attracted a number of researchers [9,10]. These transition metal complexes of Schiff's base with different chemical, physical and structural properties provide the platform for research to the number of researchers [11].…”

Section: Biological Importance Of Semicarbazones and Thiosemicarbazonesmentioning

confidence: 99%

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

Jain¹,

Kumar²,

Chandra³

2018

Asian J. Chem.

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“…Thiosemicarbazone derivatives, which play an important role in organic and medicinal chemistry, have attracted a large number of researchers over the years because of their promising biological activities, such as antioxidant [1,2], antiparasitic [3][4][5][6], anticonvulsant [7], antiviral [8][9][10]. Especially, in recent years, large of publications focused on synthesis and antimicrobial [11][12][13][14][15], anticancer [12,14,[16][17][18][19][20] activity of thiosemicarbazones to find out the potential candidates to develop new drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons

Pham

Phan

et al. 2020

Molecules

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Reaction of 4-(1-adamantyl)-3-thiosemicarbazide (1) with numerous substituted acetophenones and benzaldehydes yielded the corresponding thiosemicarbazones containing adamantane skeletons. The synthesized compounds were evaluated for their in vitro activities against some Gram-positive and Gram-negative bacteria, and the fungus Candida albicans, and cytotoxicity against four cancer cell lines (Hep3B, HeLa, A549, and MCF-7). All of them showed good antifungal activity against Candida albicans. Compounds 2c, 2d, 2g, 2j and 3a, 3e, 3g displayed significant inhibitory activity against Enterococcus faecalis. Compounds 2a, 2e, 2h, 2k and 3j had moderate inhibitory potency against Staphylococcus aureus. Compounds 2a, 2e and 2g found so good inhibitory effect on Bacillus cereus. Compounds 2d and 2h, which contain (ortho) hydroxyl groups on the phenyl ring, were shown to be good candidates as potential agents for killing the tested cancer cell lines, i.e., Hep3B, A549, and MCF-7. Compounds 2a–c, 2f, 2g, 2j, 2k, 3g, and 3i were moderate inhibitors against MCF-7.

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Design, synthesis and anticancer activity of novel nopinone-based thiosemicarbazone derivatives

Cited by 62 publications

References 30 publications

Design, synthesis and in vitro evaluation of new thiosemicarbazone derivatives as potential anticancer agents

Design, synthesis and in vitro evaluation of new thiosemicarbazone derivatives as potential anticancer agents

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons

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