Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(31), P. 6042 - 6046
Published: Jan. 1, 2020
3-Allyl-3-hydroxyoxindoles are obtained with high ee in a metal-free catalytic process from isatins. This scaffold has been converted to the natural product chimonamidine.
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(26), P. 10316 - 10320
Published: March 10, 2020
Abstract A mild visible‐light‐induced Pd‐catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage a C(sp 2 )−O bond, leading to hybrid aryl Pd‐radical intermediates. following 1,5‐hydrogen atom translocation, cyclization, and rearomatization steps lead valuable oxindole isoindoline‐1‐one motifs. Notably, this provides access products with readily enolizable functional groups that are incompatible traditional conditions.
Language: Английский
Citations
99
European Journal of Medicinal Chemistry, Journal Year: 2020, Volume and Issue: 211, P. 113102 - 113102
Published: Dec. 18, 2020
Language: Английский
Citations
97
Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(20), P. 11817 - 11893
Published: Oct. 4, 2023
Enantioconvergent catalysis has expanded asymmetric synthesis to new methodologies able convert racemic compounds into a single enantiomer. This review covers recent advances in transition-metal-catalyzed transformations, such as radical-based cross-coupling of alkyl electrophiles with nucleophiles or alkylmetals and reductive two mainly under Ni/bis(oxazoline) catalysis. C–H functionalization can be performed an enantioconvergent manner. Hydroalkylation alkenes, allenes, acetylenes is alternative reactions. Hydrogen autotransfer been applied amination alcohols C–C bond forming reactions (Guerbet reaction). Other metal-catalyzed involve addition allylic systems carbonyl compounds, propargylation phenols, 3-bromooxindoles, allenylation allenolates propargyl bromides, hydroxylation 1,3-dicarbonyl compounds.
Language: Английский
Citations
39
Tetrahedron, Journal Year: 2025, Volume and Issue: 177, P. 134565 - 134565
Published: Feb. 28, 2025
Language: Английский
Citations
1
The Chemical Record, Journal Year: 2021, Volume and Issue: 21(4), P. 924 - 1037
Published: Feb. 18, 2021
Abstract Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance the fields of organic and medicinal chemistry. Isatin, due its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles 3,3‐disubstituted oxindoles) even, under certain conditions, ring‐opening occur that leads other heterocyclic compounds. Over past few years, new methodologies have been described for this important easily available starting material MCRs. In review, we explore these novelties, displaying them according structure final products obtained.
Language: Английский
Citations
43
Bioorganic Chemistry, Journal Year: 2020, Volume and Issue: 98, P. 103753 - 103753
Published: March 19, 2020
Language: Английский
Citations
42
Tetrahedron, Journal Year: 2022, Volume and Issue: 120, P. 132893 - 132893
Published: June 22, 2022
Language: Английский
Citations
26
Organic Letters, Journal Year: 2020, Volume and Issue: 22(8), P. 2868 - 2872
Published: Feb. 12, 2020
The enantioselective vinylogous Mannich reaction of ketimines derived from isatins with acyclic vinylketene silyl acetals has been developed using a chiral bis(imidazoline)–Cu(II) catalyst. A series 3-aminooxindole derivatives bearing tetra-substituted stereogenic centers an α,β-unsaturated ester moiety were obtained in excellent yields (up to 99%) high enantioselectivities 98% ee). Enantioselective bisvinylogous also afforded product enantioselectivity. Based on the experimental investigations, possible transition state proposed explain origin asymmetric induction.
Language: Английский
Citations
29
RSC Medicinal Chemistry, Journal Year: 2022, Volume and Issue: 13(8), P. 970 - 977
Published: Jan. 1, 2022
Molecular hybridization approaches have become an important strategy in medicinal chemistry, and to this end, we developed a series of novel N-1,2,3-triazole-isatin hybrids that are promising as tumour anti-proliferative agents. Our isatin presented high cytotoxic activity against colon cancer cell line SW480, lung adenocarcinoma A549, well breast lines MCF7 MDA-MB-231. All tested compounds demonstrated better anti-proliferation (to 1-order magnitude) than the cis-platin (CDDP) benchmark. In order explore potential biological targets for these compounds, used information from previous screenings identified putative histone acetyltransferase P-300 (EP300) acyl-protein thioesterase 2 (LYPLA2), both known be involved epigenetic regulation. Advantageous pharmacological properties were predicted such good total surface area binding aromatic hydrophobic units enzyme active site. addition, found down-regulation LYPLA2 EP300 MDA-MB-231 cells treated with our inhibitors, but no significant effect was detected normal MCF10A. We also observed upregulation mRNA expression MCF10A some same one compounds. These results suggest at transcriptional regulation level associated oncological contexts.
Language: Английский
Citations
17
Frontiers in Chemistry, Journal Year: 2025, Volume and Issue: 13
Published: March 28, 2025
The Hosomi-Sakurai allylation reaction has been widely applied in the total synthesis of biologically active natural products, especially synthesising complex polycyclic compounds containing multi-stereogenic centres since its discovery 1976. is ketones and aldehyde with nucleophilic allylsilanes catalyzed Lewis acid mainly used to extend C-C bond a molecule also create new site for manipulation due facile transformation pi (π) at end chain. This review highlights only portions product synthetic works that feature or modification as key route.
Language: Английский
Citations
0