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The Widening Panorama of Natural Products Chemistry in Brazil
Published in Luzia Valentina Modolo, Mary Ann Foglio, Brazilian Medicinal Plants, 2019
Maria Fátima das Graças Fernandes da Silva, João Batista Fernandes, Moacir Rossi Forim, Michelli Massaroli da Silva, Jéssica Cristina Amaral
The alkaloids derived from anthranilic acid are the second group most isolated, for example, a simple 2-quinolone (44) and acridones (52–59). They were found in Amaranthaceae (simple 2-quinolone) and Rutaceae (acridones). The tryptophan derivative alkaloids, as terpene indole alkaloids (60–65) occur in Apocynaceae and Rubiaceae. Lysine derivatives piperidine (66–69) and pyridine (70) alkaloids were reported in Fabaceae and Piperaceae.
Inhibiting Low-Density Lipoproteins Intimal Deposition and Preserving Nitric Oxide Function in the Vascular System
Published in Christophe Wiart, Medicinal Plants in Asia for Metabolic Syndrome, 2017
Rutaceae produce quinoleic alkaloids that have the tendency to inhibit platelet aggregation in vitro. Glycosmis parviflora (Sims) Little elaborates citracridone, atalaphyllidine, des-N-methylnoracronycine, 5-nydroxynoracronycine, des-N-methylacronycine, pyranofolidine and 4,8-dimethoxy-1-methyl-3(3-methyl-2-enyl)2-quinolone which at a concentration of 100 μg/mL inhibited the aggregation of platelets induced by arachidonic acid by more than 90%.175 Citracridone, atalaphyllidine, des-N-methylnoracronycine, des-N-methylacronycine, pyranofolidine and 4,8-dimethoxy-1-methyl-3(3-methyl-2-enyl)2-quinolone at 100 μg/mL inhibited collagen-induced aggregation by more than 80%.175 Citracridone and pyranofolidine inhibited further the aggregation of platelets exposed to platelet factor by about 95%.175
Discovery of N-quinazolinone-4-hydroxy-2-quinolone-3-carboxamides as DNA gyrase B-targeted antibacterial agents
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Wenjie Xue, Yaling Wang, Xu Lian, Xueyao Li, Jing Pang, Johannes Kirchmair, Kebin Wu, Zunsheng Han, Xuefu You, Hongmin Zhang, Jie Xia, Song Wu
We previously16 proposed the likely binding mode of the N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings to the ATP binding site of S. aureus GyrB by molecular docking. Here, we utilised LigPlot+17 to generate a 2D diagram of the representative GyrB inhibitor g37. Figure 2(a) clearly shows that the 4-hydroxy-2-quinolone fragment plays the most important role in the binding to GyrB: its carbanyl group forms hydrogen bonds with Arg144, and its 4-hydroxyl group is involved in the formation of hydrogen bonds with Glu58 and Arg84. We performed a substructure search of the Specs database with the 4-hydroxy-2-quinolone fragment and identified 272 matches (in approximately 210,000 compounds). Aided by a clustering analysis and visual inspection of the molecular structures, we selected 14 potential GyrB inhibitors for experimental validation. Figure 2(b) shows that all compounds except for AE-406/41056087 and AE-406/41056637 are based on the chemotype of 4-hydroxy-2-quinolone-3-carboxamides and have diverse substituents attached to the amide nitrogen atom, i.e. thiazole, pyridine, 4-oxoquinazolin, phenyl, alkyl, oxazole, biphenyl, phenacetylamino, alkyl amide, benzamide, pyridine acetamide, and benzsulfamide.