A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles.
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http://dx.doi.org/10.3390/molecules25143227 | DOI Listing |
Beilstein J Org Chem
December 2024
Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye.
Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[]fluoranthenes, which are all structurally relevant to benzo[]fluoranthene-based fungal natural products.
View Article and Find Full Text PDFDalton Trans
July 2024
Departamento de Engenharia e Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboa, Portugal.
Monoanionic gold bis(dithiolene) complexes were recently shown to display activity against ovarian cancer cells, Gram-positive bacteria, strains and the rodent malaria parasite, . To date, only monoanionic gold(III) bis(dithiolene) complexes with a thiazoline backbone substituted with small alkyl chains have been evaluated for biomedical applications. We now analyzed the influence of the length and the hydrophobicity hydrophilicity of these complexes' alkyl chain on their anticancer and antiplasmodial properties.
View Article and Find Full Text PDFMar Drugs
January 2023
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
The present investigation of the South China Sea soft coral resulted in the discovery of six new polyoxygenated diterpenes, namely sartrocheliols A-E (, , -) along with four known ones, , , , and . Based on extensive spectroscopic data analysis, sartrocheliol A () was identified as an uncommon capnosane diterpene, while sartrocheliols B-E (, -) were established as cembrane diterpenes. They displayed diverse structural features not only at the distinctly different carbon frameworks but also at the various types of heterocycles, including the epoxide, γ-lactone, furan, and pyran rings.
View Article and Find Full Text PDFInt J Mol Sci
November 2021
Centre for Environmental Research, Sustainability and Innovation, Department of Environmental Science, School of Science, Institute of Technology Sligo, Ash Ln, Ballytivnan, F91 YW50 Sligo, Ireland.
Microalgae have received growing interest for their capacity to produce bioactive metabolites. This study aimed at characterising the antimicrobial potential of the marine dinoflagellate strain LACW11, isolated from the west of Ireland. Amphidinolides have been identified as cytotoxic polyoxygenated polyketides produced by several species.
View Article and Find Full Text PDFMolecules
July 2020
Dipartimento di Farmacia, Università di Genova, viale Cembrano 4, 16147 Genova, Italy.
A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles.
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