Two new oxindole alkaloid glycosides, nauclealomide A and (3S,7R)-javaniside, were isolated from the leaves of Nauclea officinalis. Their structures and absolute configurations were elucidated by means of NMR, HRESIMS, X-ray diffraction, acid hydrolysis and quantum chemical CD calculation. Nauclealomide A is a novel monoterpenoid oxindole alkaloid possessing a rare tetrahydro-2H-1,3-oxazine ring.
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Org Biomol Chem
January 2025
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China.
A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS has been developed by using xanthate salts as alkyl radical precursors in the presence of tricyclohexylphosphine. It proceeds through a tandem radical addition/cyclization process, and this protocol provides a reliable and practical approach to building the skeleton of 3,3-disubstituted oxindoles in moderate to good yields. Notable features of this reaction include readily available starting reagents, broad substrate scope and mild reaction conditions.
View Article and Find Full Text PDFPharmaceuticals (Basel)
November 2024
Laboratory of Nanobiotechnologies, Saint-Petersburg National Research Academic University of the Russian Academy of Sciences, Saint Petersburg 194021, Russia.
: A series of spiro-fused heterocyclic compounds containing cyclopropa[a]pyrrolizidine-2,3'-oxindole and 3-spiro[3-azabicyclo[3.1.0]-hexane]oxindole frameworks were synthesized and studied for their in vitro antiproliferative activity against human erythroleukemia (K562), cervical carcinoma (HeLa), acute T cell leukemia (Jurkat), melanoma (Sk-mel-2) and breast cancer (MCF-7) as well as mouse colon carcinoma (CT26) cell lines.
View Article and Find Full Text PDFA one-pot, acid-, base-, and metal-free, multicomponent strategy has been developed to synthesize spiro thiochromene-oxindole derivatives as potential anti-inflammatory agents. The synthesized compounds were screened for their anti-inflammatory activity by inhibiting heat-induced Bovine Serum Albumin (BSA) denaturation assay, revealing moderate to good efficacy. Compounds 4e, 4k, and 4h exhibited the highest activity, inhibiting BSA denaturation by 90.
View Article and Find Full Text PDFChemMedChem
December 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
An efficient and concise synthesis of highly functionalized bridged coumarins has been developed through a diastereoselective double Michael addition reaction of p-quinols with various 4-hydroxy coumarins under catalyst-free conditions in HO-DMSO (8 : 2). The method has been applied to oxindoles for the synthesis of a variety of bridged-oxindoles and bridged-spiroxindoles in presence of a DABCO base using HO-EtOH (8 : 2) as solvent medium. The strategy is simple, highly atom economical as there is no by-product and environmentally benign (E-factor=0.
View Article and Find Full Text PDFMolecules
November 2024
LAQV-REQUIMTE, Institute for Research and Advanced Studies, University of Évora, Rua Romão Ramalho, 59, 7000-641 Évora, Portugal.
The 3-component Passerini reaction (3CPR), discovered little more than 100 years ago, has been demonstrated in the last few decades to be a valuable tool for accessing structural diversity and complexity, essential topics to consider in drug discovery programs. Focusing on accessing a fine-tuned family of α-acyloxyamide-oxindole hybrids, we underline herein our latest insights regarding the use of this mild reaction approach to obtain promising anticancer agents. Cheap and commercially available isatin was used as starting material.
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