A BF·OEt catalyzed intramolecular Povarov reaction was used to synthesize 15 chromenopyridine fused thiazolino-2-pyridone peptidomimetics. The reaction works with several -alkylated salicylaldehydes and amino functionalized thiazolino-2-pyridones, to generate polyheterocycles with diverse substitution. The synthesized compounds were screened for their ability to bind α-synuclein and amyloid β fibrils . Analogues substituted with a nitro group bind to mature amyloid fibrils, and the activity moreover depends on the positioning of this functional group.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660745 | PMC |
| http://dx.doi.org/10.1021/acs.joc.0c01699 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
π-Expanded azaullazines: synthesis of quinolino-azaullazines by Povarov reaction and cycloisomerisation.
Org Biomol Chem
March 2024
Institute of Chemistry, University Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Doping and extension of polycyclic aromatic hydrocarbons (PAHs) by simple and efficient synthetic methods is of increased demand for the development of novel and improved organic electronics. Diarylindolizino[6,5,4,3-]quinolino[2,3-][1,6]naphthyridines (quinolino-azaullazines) were prepared by combination of Pd catalyzed cross-coupling with Povarov and cycloisomerisation reactions. The products contain an electron-rich ullazine and an electron-poor quinoline moiety and show intramolecular charge transfer properties that can be tuned by the substitution pattern.
View Article and Find Full Text PDFA Molecular Electron Density Theory Study of the Domino Reaction of -Phenyl Iminoboranes with Benzaldehyde Yielding Fused Bicyclic Compounds.
Molecules
August 2023
Department of Organic Chemistry, University of Valencia, Dr. Moliner 50, 46100 Burjassot, Spain.
The reaction of -phenyl iminoborane with benzaldehyde yielding a fused aromatic compound, recently reported by Liu et al., has been studied within the Molecular Electron Density Theory (MEDT). Formation of the fused aromatic compound is a domino process that comprises three consecutive reactions: (i) formation of a weak molecular complex between the reagents; (ii) an intramolecular electrophilic attack of the activated carbonyl carbon of benzaldehyde on the position of the -phenyl substituent of iminoborane; and (iii) a formal 1,3-hydrogen shift yielding the final fused aromatic compound.
View Article and Find Full Text PDFThe Intramolecular Povarov Tool in the Construction of Fused Nitrogen-Containing Heterocycles.
Top Curr Chem (Cham)
May 2023
Departamento de Química Orgánica I, Facultad de Farmacia and Centro de Investigación Lascaray (Lascaray Research Center), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), Paseo de la Universidad 7, 01006, Vitoria-Gasteiz, Spain.
Nitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today's most desirable synthetic targets and the Povarov reaction is a powerful synthetic tool for the construction of highly functionalized heterocyclic systems. This process involves an aromatic amine, a carbonyl compound, and an olefin or acetylene to give rise to the formation of a nitrogen-containing heterocycle.
View Article and Find Full Text PDFSkeleton-Reorganizing Coupling Reactions of Cycloheptatriene and Cycloalkenones with Amines.
Angew Chem Int Ed Engl
January 2023
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
Skeletal reorganization reactions have emerged as an intriguing tool for converting readily available compounds into complicated molecules inaccessible by traditional methods. Herein, we report a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. In the presence of Rh/acid catalysis, cycloheptatriene can selectively couple with anilines to deliver fused 1,2-dihydroquinoline products.
View Article and Find Full Text PDFDiastereoselective intramolecular cyclization/Povarov reaction cascade for the one-pot synthesis of polycyclic quinolines.
Org Biomol Chem
July 2022
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str., 8, Kazan, Russian Federation.
The method for the synthesis of complex alkaloid-like aza-heterocycles has been developed through the Povarov reaction of generated 2-oxoimidazolium cations. The reaction lead to the formation of 2 C-N, 2 C-C bonds and three stereocentres, and features excellent regio- and diastereoselectivity. Based on the controlled experiments and quantum chemistry data, the mechanism of the reaction cyclization was proposed and diastereoselectivity origins were rationalized.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!