A one-pot protocol for the diversity-oriented synthesis of two indole-based annulated polyheterocycles, ketoindoloquinoxalines and indolotriazoloquinoxalines, has been described. The salient features of the methodology involves either a metal/O2-catalyzed aminooxygenation or a [3 + 2] cycloaddition pathway.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo402783p | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Diazacyclic and Triazacyclic Small-Molecule Libraries Using Vicinal Chiral Diamines Generated from Modified Short Peptides and Their Application for Drug Discovery.
Pharmaceuticals (Basel)
November 2024
Herbert Wertheim College of Medicine, Center for Translational Science, Florida International University, Port Saint Lucie, FL 34987, USA.
Small-molecule probes are powerful tools for studying biological systems and can serve as lead compounds for developing new therapeutics. Especially, nitrogen heterocycles are of considerable importance in the pharmaceutical field. These compounds are found in numerous bioactive structures.
View Article and Find Full Text PDFDiverse Synthesis of Arene-Fused [n.1.1]-Bridged Molecules via Catalytic Cycloaddition and Rearrangement Reactions.
Angew Chem Int Ed Engl
December 2024
Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, China.
Although great advancement has been made in synthesis of 3D bridged bicyclic[n.1.1]-bioisosteres, facile construction of 2D/3D merged molecules incorporating bridged rings, as novel chemical space in drug discovery, remains a significant challenge.
View Article and Find Full Text PDFSugar Auxiliary Group Assisted Diversity-Oriented Enzymatic Modular Synthesis of 0-Series Ganglioside Glycans.
Angew Chem Int Ed Engl
December 2024
Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, China.
Owing to the inaccessibility of β1-4-N-acetylgalactosaminyltransferase for direct glycan chain elongation, the enzymatic synthesis of 0-series gangliosides with extended backbones has not been explored. In this study, sialic acid was enzymatically introduced as an auxiliary group to overcome the limitation of substrate specificity of Campylobacter jejuni β1-4-N-acetylgalactosaminyltransferase (CjCgtA) to achieve the synthesis of desired extended 0-series ganglioside core structures, and the sialic acid auxiliary group could be removed by sialidase at appropriate stages. A bacterial α2-6-sialyltransferase from Photobacterium damselae (Pd2,6ST) exhibited unexpected acceptor substrate specificity for 0-series ganglioside core structures, providing ready access to complex gangliosides bearing the sialyl N-acetylgalactosamine unit.
View Article and Find Full Text PDFThe Synthesis of Sulfonyl Fluoride Functionalized 2-Aminothiazoles Using a Diversity Oriented Clicking Strategy.
Org Lett
December 2024
Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, VIC 3052, Australia.
We present a Diversity Oriented Clicking approach to synthesize a library of novel clickable -substituted 2-aminothiazoles which serve as versatile hubs for SuFEx click chemistry diversification. Leveraging the spring-loaded reactivity of the 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) connectors, the transformation is simple to perform, tolerant of a wide range of functionality, and regioselective for a single product. Finally, we propose a detailed stepwise reaction mechanism that is supported by experimental and computational analysis.
View Article and Find Full Text PDFSynthesis of Spin-Labeled α-/β-Galactosylceramides and Glucosylceramides as Electron Paramagnetic Probes.
J Org Chem
December 2024
Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
α-/β-Galactosylceramide (GalCer) and glucosylceramide (GlcCer) derivatives having a radical label at the 6--position suitable for electron paramagnetic resonance spectroscopic studies were synthesized by a diversity-oriented strategy that is highlighted by the efficient glycosylation of a lipid precursor and late-stage ceramide assembly to enable lipid diversification. The strategy was also utilized to synthesize natural α-/β-GalCers and GlcCers. Furthermore, the involved azido-intermediates are flexible platforms to access various other GalCer and GlcCer derivatives.
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!