The Eighth Central European Conference “Chemistry towards Biology”: Snapshot

Perczel, András; Atanasov, Atanas G.; Sklenář, Vladimı́r; Nováček, Jiří; Papoušková, Veronika; Kadeřávek, Pavel; Žı́dek, Lukáš; Kozłowski, Henryk; Wątły, Joanna; Hecel, Aleksandra; Kołkowska, Paulina; Koča, Jaroslav; SvobodováVařeková, Radka; Pravda, Lukáš; Sehnal, David; Horský, Vladimír; Geidl, Stanislav; Enriz, Ricardo D.; Matějka, Pavel; Jeništová, Adéla; Dendisová, Marcela; Kokaislova, A.; Weissig, Volkmar; Olsen, Mark; Coffey, Aidan; Ajuebor, Jude; Keary, Ruth; Sanz-Gaitero, Marta; Raaij, Mark J. van; McAuliffe, Olivia; Waltenberger, Birgit; Mocan, Andrei; Šmejkal, Karel; Heiss, Elke H.; Diederich, Marc; Musioł, Robert; Košmrlj, Janez; Polański, Jarosław; Jampílek, Josef

doi:10.3390/molecules21101381

Cited by 5 publications

(4 citation statements)

References 131 publications

(130 reference statements)

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“…During the 20 th century, the natural origin was in most cases replaced by synthetic drugs. Nowadays, we can see a reversing trend; natural medicine reappears in many areas of medicine (Perczel et al 2016) and some of the used nature-originated drugs belong to alkaloids (e.g., galanthamine, paclitaxel). However, the usage of pure alkaloids has a longer history, e.g.…”

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confidence: 99%

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

et al. 2017

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Quaternary benzophenanthridine alkaloids are known to have a wide range of biological effects, including antimicrobial, antifungal, anti-inflammatory, and antitumour activities. However, only sanguinarine and chelerythrine have been studied intensively. The aim of this study was to evaluate the anti-inflammatory potential of the five minor quaternary benzophenanthridine alkaloids sanguilutine, sanguirubine, chelirubine, chelilutine, and macarpine in vitro and to compare them with more thoroughly studied sanguinarine and chelerythrine. Before making cellbased assays, the cytotoxicity of the alkaloids was evaluated. The anti-inflammatory potential of the chosen alkaloids was evaluated as for their ability to modulate the lipopolysaccharideinduced secretion of tumour necrosis factor α (TNF-α) in the macrophage-like cell line THP-1. The cyclooxygenase (COX)-1 and COX-2 inhibitory activities were also measured. The results indicate that the presence of a methylenedioxy ring attached at carbon (C)7-C8 is important for reducing the secretion of TNF-α. Interestingly, this effect did not show a simple dependence on concentration. The selected alkaloids showed little or no anti-COX activity. The results obtained from the present experiments may provide additional information useful in understanding the structure-to-activity relationship of the quaternary benzophenanthridine alkaloids. The antiinflammatory potential and the cytotoxic effect are driven by the presence of a methylenedioxy ring attached at C7-C8 and C2-C3, respectively.

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confidence: 99%

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

et al. 2017

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“…We have been interested in the structural development of Sorafenib using a 1,2,3-triazole ring as a component in the structure, since we envisioned that this aromatic heterocycle should interact well with the pocket of the targets by providing hydrogen bonds, π-π, and hydrophobic interactions. Furthermore, its structure is similar to amino acid histidine, leading to bio-compatibility [ 43 , 44 ], which has been proven to resist metabolism [ 4 , 45 ]. This structure also exists in a wide range of bioactive compounds including anti-cancer agents [ 4 , 37 , 46 , 47 , 48 ].…”

Section: Introductionmentioning

confidence: 99%

The Design and Synthesis of a New Series of 1,2,3-Triazole-Cored Structures Tethering Aryl Urea and Their Highly Selective Cytotoxicity toward HepG2

et al. 2022

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Target cancer drug therapy is an alternative treatment for advanced hepatocellular carcinoma (HCC) patients. However, the treatment using approved targeted drugs has encountered a number of limitations, including the poor pharmacological properties of drugs, therapy efficiency, adverse effects, and drug resistance. As a consequence, the discovery and development of anti-HCC drug structures are therefore still in high demand. Herein, we designed and synthesized a new series of 1,2,3-triazole-cored structures incorporating aryl urea as anti-HepG2 agents. Forty-nine analogs were prepared via nucleophilic addition and copper-catalyzed azide-alkyne cycloaddition (CuAAC) with excellent yields. Significantly, almost all triazole-cored analogs exhibited less cytotoxicity toward normal cells, human embryonal lung fibroblast cell MRC-5, compared to Sorafenib and Doxorubicin. Among them, 2m’ and 2e exhibited the highest selectivity indexes (SI = 14.7 and 12.2), which were ca. 4.4- and 3.7-fold superior to that of Sorafenib (SI = 3.30) and ca. 3.8- and 3.2-fold superior to that of Doxorubicin (SI = 3.83), respectively. Additionally, excellent inhibitory activity against hepatocellular carcinoma HepG2, comparable to Sorafenib, was still maintained. A cell-cycle analysis and apoptosis induction study suggested that 2m’ and 2e likely share a similar mechanism of action to Sorafenib. Furthermore, compounds 2m’ and 2e exhibit appropriate drug-likeness, analyzed by SwissADME. With their excellent anti-HepG2 activity, improved selectivity indexes, and appropriate druggability, the triazole-cored analogs 2m’ and 2e are suggested to be promising candidates for development as targeted cancer agents and drugs used in combination therapy for the treatment of HCC.

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“…As part of our endeavor in quinoline-2,4-dione chemistry [10] as well as functional click triazoles [11,12] and their applications [13], we became interested in the synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones 2 that may potentially serve as functional scaffolds in coordination chemistry, molecular sensing and biochemistry. It is noteworthy that many compounds with the quinoline-2,4-dione structure were isolated from fungi, bacteria and plants, possessing broad range of interesting biological activities in vitro and in vivo [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones

et al. 2018

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Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.

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The Eighth Central European Conference “Chemistry towards Biology”: Snapshot

Cited by 5 publications

References 131 publications

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

The Design and Synthesis of a New Series of 1,2,3-Triazole-Cored Structures Tethering Aryl Urea and Their Highly Selective Cytotoxicity toward HepG2

Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones

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