This work highlights the literature of one of the most valuable moieties in the field of organic chemistry. In this review, the chemistry of tetronic acid as a simple precursor to privileged heterocyclic motifs is described. The synthetic procedures of different fused heterocycles incorporating a furan moiety are described. Fused heterocycles are classified as bicyclic, tricyclic, tetracyclic and spiro-fused pyran derivatives.
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http://dx.doi.org/10.1007/s11030-016-9683-x | DOI Listing |
Beilstein J Org Chem
October 2024
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation.
For the first time, recyclization of allomaltol derivatives with an amide fragment in the side chain were investigated. It was shown that the studied process leads to substituted tetronic acids bearing a pyrrolidinone moiety. The application of 1,1'-carbonyldiimidazole and DBU is necessary for implementation of the considered reaction.
View Article and Find Full Text PDFChemistry
November 2024
CICA-Centro Interdisciplinar de Química e Bioloxía, Departamento de Química, Facultade de Ciencias, Universidade da Coruña, A Coruña, 15071, Spain.
Human Adenovirus (HAdV) infections in immunocompromised patients can result in disseminated diseases with high morbidity and mortality rates due to the absence of available treatments for these infections. The sponge Ircinia felix was selected for the significant anti-HAdV activity displayed by its organic extracts. Its chemical analysis yielded three novel sesterterpene lactams, ircinialactams J-L, along with three known sesterterpene furans which structures were established by a deep spectrometric analysis.
View Article and Find Full Text PDFPest Manag Sci
October 2024
Institute of Pesticide Science, College of Plant Protection, Southwest University, Chongqing, China.
Background: Plants have numerous defensive secondary metabolites to withstand insect attacks. Scoparone, which is extracted from the medicinal plant Artemisia capillaris, has potent acaricidal effects on Tetranychus cinnabarinus. Spirodiclofen, derived from a tetronic acid derivative, is a potent commercial acaricide that is extensively used globally.
View Article and Find Full Text PDFEnviron Pollut
February 2024
College of Marine Sciences, South China Agricultural University, Guangzhou, 510640, PR China. Electronic address:
Spirotetramat (SPT), a tetronic acid-derived insecticide, is implicated in reproductive and lipid metabolism disorders, as well as developmental toxicity in fish. While these effects are documented, the precise mechanisms underlying its developmental toxicity are not fully elucidated. In this study, zebrafish embryos (2 h post-fertilization, hpf) were exposed to four concentrations of SPT (0, 60, 120, and 240 μg/L) until 21 dpf (days post-fertilization).
View Article and Find Full Text PDFFitoterapia
October 2023
Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China. Electronic address:
Three new tetronic acid derivatives, nodulisporacid A ethyl ester (3), isosporothric acid methyl ester (4), and (R)-3-(methoxycarbonyl)-2-methyleneundecanoic acid (5) were isolated from mangrove endophytic fungus Hypomontagnella monticulosa YX702, together with three known analogues nodulisporacid A (1), nodulisporacid A methyl ester (2), and dihydrosporothriolide (6). The structures of these new compounds were elucidated by analysis of NMR and HR-ESI-MS spectroscopic data. In addition, the absolute configuration of nodulisporacid A (1) was confirmed by single-crystal X-ray diffraction for the first time.
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