Thiophene-2-carboxamide derivatives of anthraquinone: A new potent antitumor chemotype

Volodina, Yulia L.; Тихомиров, А. С.; Dezhenkova, Lyubov G.; Ramonova, Alla A.; Kononova, Anastasia V.; Andreeva, Daria V.; Kaluzhny, Dmitry N.; Schols, Dominique; Moisenovich, Mikhail M.; Shchekotikhin, Andrey E.; Shtil, Alexander А.

doi:10.1016/j.ejmech.2021.113521

Cited by 18 publications

(8 citation statements)

References 53 publications

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“…52 Moreover, studies have discussed the antitumor activity of various derivatives of thiophene-2-carboxamide, thiophene-3-carboxamide, and furan-2-carboxamide. 52–54 In our work, we have prepared the core of these compounds with good yields as shown in the substrate scope, 9w , 9x , and 9u respectively.…”

Section: Resultsmentioning

confidence: 98%

Hydrogen bond mediated conversion of benzenenitriles and arylacetonitriles to amides: an “on/in-water” reaction strategy

2022

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Section: Resultsmentioning

confidence: 98%

Hydrogen bond mediated conversion of benzenenitriles and arylacetonitriles to amides: an “on/in-water” reaction strategy

2022

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“…These findings demonstrated that the electron-withdrawing group on the aromatic ring linked to the thiazole ring had a major impact on activity. [54,55] Compounds 2b containing 4-nitrophenyl moieties, and 2c containing phenyl moieties were shown to have potent antitumor action. The reason for this is hydrophobic interactions between the phenyl group and the active site in the caspase-3 binding pocket.…”

Section: Results Of Dft Studiesmentioning

confidence: 99%

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Nuha

Evren

Çiyanci

et al. 2022

Archiv der Pharmazie

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Within the scope of this study, new 2-{2-[(5-nitrothiophen-2-yl)methylene] hydrazinyl}thiazole derivatives (2a-j) were synthesized and investigated for their potential anticancer and enzyme inhibition activities. Spectroscopic techniques were used to determine the structures of substances. The anticancer activities of compounds were detected in A549 human lung carcinoma and L929 murine fibroblast cell lines, determining cytotoxicity, apoptosis, mitochondrial membrane integrity, and caspase-3 activation. Compounds 2b bearing 4-nitrophenyl, 2c bearing phenyl, and 2d bearing 4-cyanophenyl moieties were specified with high anticancer activity, acting through an apoptotic pathway with an apoptosis ratio of 9.61%-15.59%. Mitochondrial membrane depolarization was determined to be 25.53% and 22.33% for compounds 2b and 2c, respectively. Furthermore, compound 2c exhibited excellent caspase-3 activation. A molecular docking study was realized with compound 2c on the caspase-3 enzyme. Furthermore, the electronic characteristics of the active compounds were investigated using density functional theory (DFT) at the B3LYP/6-31G (d, p) level. The frontier molecular orbital energy and atomic net charges were examined.

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“…Some compounds with anthraquinone nucleus are also on the market, such as mitoxantrone, diacerein, and amrubicin [ 53 ]. Recently, with a series of biological evaluations, Volodina et al [ 54 ] reported a thiophene-2-carboxamide derivative of anthraquinone (compound 8 ) as a new potent antitumor chemotype, showing the promising anticancer effects of anthraquinone compounds. Despite this, the toxic assessment of this compound or the identification of toxic moieties, such as anthraquinone and the bis (2-hydroxyethyl) amino group, will be meaningful for drug safety.…”

Section: Discussionmentioning

confidence: 99%

Structure-Based Discovery and Biological Assays of a Novel PRMT5 Inhibitor for Non-Small Cell Lung Cancer

Chen

Zhang

et al. 2022

Molecules

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Protein arginine methyltransferase 5 (PRMT5) is a popular anticancer target that regulates histone or nonhistone methylation and is linked to the development and poor prognosis of non-small cell lung cancer. PRMT5 inhibitors have shown great promise in clinical trials as a cancer therapy. However, most inhibitors reported recently act in a SAM-competitive mode and lack structural diversity. In this paper, a novel non-SAM inhibitor, 3039-0164, was discovered by the structure-based virtual screening method. The binding mechanism of 3039-0164 to PRMT5 was revealed via molecular docking and molecular dynamics simulations. 3039-0164 inhibited PRMT5 enzymatic activity, downregulated the expression of PRMT5 downstream target genes (FGFR3 and eIF4E), and blocked the activation of the PI3K/AKT/mTOR and ERK signaling pathways. The discovery of 3039-0164 provides precise and creative hit compounds for the design optimization of PRMT5 lead compounds in non-small cell lung cancer.

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Thiophene-2-carboxamide derivatives of anthraquinone: A new potent antitumor chemotype

Cited by 18 publications

References 53 publications

Hydrogen bond mediated conversion of benzenenitriles and arylacetonitriles to amides: an “on/in-water” reaction strategy

Hydrogen bond mediated conversion of benzenenitriles and arylacetonitriles to amides: an “on/in-water” reaction strategy

Synthesis, density functional theory calculation, molecular docking studies, and evaluation of novel 5‐nitrothiophene derivatives for anticancer activity

Structure-Based Discovery and Biological Assays of a Novel PRMT5 Inhibitor for Non-Small Cell Lung Cancer

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