Three new antibacterial spirooxindole alkaloids, spirobrefeldins A-C (1-3), together with four known analogs, spirotryprostatin M (4), spirotryprostatin G (5), 12β-hydroxyverruculogen TR-2 (6), and 12α-hydroxyverruculogen TR-2 (7), were isolated from terrestrial fungus All the new compounds were elucidated extensively by the interpretation of their NMR (1D and 2D) spectra and high-resolution mass data, and their absolute configurations were determined by computational chemistry and CD spectra. The absolute configurations of spiro carbon C-2 in spirotryprostatin G (5) and spirotryprostatin C in literature were reported as , which were revised to based on experimental and calculated CD spectra. All the compounds were evaluated for their antimicrobial activities toward PAO1, EC1, , , and . Compound 7 displayed moderate inhibitory activity toward dimorphic switch of pathogenic smut fungi at 25 μM. Compounds 3 and 6 showed weak antibacterial activities against phytopathogenic bacterial EC1 at 100 μM.
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http://dx.doi.org/10.3389/fmicb.2022.1046099 | DOI Listing |
Antiinflamm Antiallergy Agents Med Chem
November 2024
Department of Pharmaceutics and Pharmaceutical Technology, Faculty of Pharmacy, University of Jordan, Amman, Jordan.
Background: A series of novel 2-(isoquinolin-1-yl)-spiro[oxindole-3,3'-pyrrolines] were synthesized by a one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 3-phenylimidazo[5,1-a]isoquinoline and N-alkylisatins in chloroform at ∼60°C for 24 h.
Aims: This study aimed at the synthesis of novel spirooxindole-3,3'-pyrrolines derivatives and in vitro evaluation of cytotoxicity affinities in cross-correlations with their anti-inflammation and radical scavenging capacities.
Objectives: The objective of this study was to use a one-pot, three-component reaction to synthesize a novel set of spirooxindole-3,3'-pyrrolines derivatives.
Mol Divers
July 2024
Department of Chemistry, Guru Jambheshwar University of Science & Technology, Hisar, Haryana, 125001, India.
Inspired from the important applications of spirocyclic compounds in medicinal chemistry, a new series of pyrazoline Spiro-oxindole tethered 1,2,3-triazole hybrids was reported via Cu(I)-catalyzed click reaction from isatin-pyrazoline linked terminal alkynes with in situ derived benzyl azides. Antimicrobial evaluation data showed that all hybrids exhibited promising efficacy towards the tested microbial strains. Antimicrobial screening as well as docking studies suggested that hybrid 6a was found to be most potent towards Aspergillus niger (MIC = 0.
View Article and Find Full Text PDFInorg Chem
April 2024
Department of Phytochemistry, Medicinal Plant and Drugs research Institute, Shahid Beheshti University, Evin, Tehran 1983963113, Iran.
The use of click chemistry as a smart and suitable method for the development of new heterogeneous catalysts is based on metal-organic frameworks as well as the production of organic compounds. The development of the click chemistry method can provide a new strategy to achieve superior properties of MOFs. Here, the two metals Co and Fe are used to create a bimetallic-organic framework.
View Article and Find Full Text PDFChem Biodivers
June 2024
Department of Microbiology, Faculty of Science, University of Mazandaran, Babolsar, 47416-95447, Iran.
This article reports one-pot synthesis of ten novel spirooxindoles using 5-methyl-2-thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65-90 %). The structures of the synthesized compounds were deduced by H-NMR, C NMR, FT-IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby-Bauer method.
View Article and Find Full Text PDFMolecules
November 2023
Faculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany.
In a sustained search for novel potential drug candidates with multispectrum therapeutic application, a series of novel spirooxindoles was designed and synthesized via regioselective three-component reaction between isatin derivatives, 2-phenylglycine and diverse arylidene-imidazolidine-2,4-diones (Hydantoins). The suggested stereochemistry was ascertained by an X-ray diffraction study and NMR spectroscopy. The resulting tetracyclic heterocycles were screened for their in vitro in vivo anti-inflammatory and analgesic activity and for their in vitro antimicrobial potency.
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