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A Rh(OAc) catalyzed three-component reaction of vinyl diazosuccinimides with alcohols and isatins has been reported, which provides a practical assess to the direct assembly of succinimide and isatin hybrid molecules in good-to-high yields with excellent stereoselectivity. The antiproliferation activity of these synthesized succinimide and isatin hybrid products has been tested via the CCK8 assay in different cancer cell lines, and compounds 4g (SJSA-1, IC = 3.82 μM) and 4r (HCT-116, IC = 9.02 μM) exhibit higher anticancer potency than other tested compounds.
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http://dx.doi.org/10.1007/s11030-022-10457-x | DOI Listing |
J Org Chem
April 2025
Saint Petersburg Academic University, ul. Khlopina 8/3, St. Petersburg 194021, Russian Federation.
An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides and itaconimides has been investigated. These reactions afford the corresponding spiro and dispiro[1-azabicyclo[3.2.
View Article and Find Full Text PDFChem Asian J
January 2024
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
A thiourea organocatalyst efficiently promoted the asymmetric cascade Michael/Michael reactions between isatin-derived trifluoromethylacrylate and α-alkylidene succinimide, resulting in high yields of spirooxindole derivatives. These compounds exhibit vicinal all-carbon quaternary stereocenters and bear a trifluoromethyl group, with excellent enantioselectivities reaching up to 99 % ee. This work represents the first successful organocatalyst application for the direct construction of vicinal all-carbon quaternary stereocenters, featuring a trifluoromethyl group.
View Article and Find Full Text PDFChemosphere
December 2022
School of Advanced Sciences, KLE Technological University, Hubballi, 580031, Karnataka, India. Electronic address:
In this paper, an environmentally benign silica-supported perchloric acid (HClO-SiO) catalyzed green FCDR strategy has been developed for the synthesis of (Z)-THIs (6) with high stereospecificity via an intramolecular hydrogen bond (IHB) directed approach, involving the reaction of methyl ketones (1), N-bromosuccinimide (NBS) (2), isatins (4) and thiosemicarbazide (5) in ethanol at reflux temperature for 45-60 min in one-pot. The reaction proceeds through the construction of C-Br (α-bromination), C-S & C-N (heterocyclization), and CN (condensation) bonds in one pot. The absolute structure of the compound (Z)-3-(2-(4-(4-bromophenyl)thiazol-2-yl)hydrazono)indolin-2-one (6e) has been confirmed by single-crystal XRD analysis.
View Article and Find Full Text PDFMol Divers
April 2023
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat Sen University, Guangzhou, 510006, Guangdong, China.
A Rh(OAc) catalyzed three-component reaction of vinyl diazosuccinimides with alcohols and isatins has been reported, which provides a practical assess to the direct assembly of succinimide and isatin hybrid molecules in good-to-high yields with excellent stereoselectivity. The antiproliferation activity of these synthesized succinimide and isatin hybrid products has been tested via the CCK8 assay in different cancer cell lines, and compounds 4g (SJSA-1, IC = 3.82 μM) and 4r (HCT-116, IC = 9.
View Article and Find Full Text PDFMolecules
April 2020
Technische Universität Dortmund, Anorganische Chemie Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
A novel [3+2]-cycloaddition reaction of 3-arylidene-1-phenyl-succinimides, cyclic 1,2-diketones (isatin, 5-chloro-isatin and acenaphtenequinone), and diverse aminoacids such as 2-phenylglycine or sarcosine is reported. The reaction provides succinimide-substituted dispiropyrrolidine derivatives with high regio- and diastereoselectivities under mild reaction conditions. The stereochemistry of these heterocycles has been confirmed by four X-ray diffraction studies.
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