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Herein we describe our efforts using a late stage functionalization together with more traditional synthetic approaches to generate fluorinated analogues of the clinical candidate AZD9833. The effects of the addition of fluorine on the lipophilicity, permeability, and metabolism are discussed. Many of these changes were tolerated in terms of pharmacology and resulted in high quality molecules which reached advanced stages of profiling in the testing cascade.
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http://dx.doi.org/10.1021/acsmedchemlett.0c00505 | DOI Listing |
Chemistry
December 2024
Fraunhofer Institute for Microengineering and Microsystems: Fraunhofer-Institut fur Mikrotechnik und Mikrosysteme IMM, Division Chemistry, Sustainable Syntheses Group, Carl-Zeiss-Straße 18-20, 55129, Mainz, GERMANY.
The selective decarboxylative fluorination of 3-oxo-3-phenylpropionic acid is used as a benchmark reaction to optimize it under biocompatible conditions in batch and to transfer it to continuous flow mode. The reaction conditions are varied with respect to temperature, fluorinating reagents, inorganic base additives, and pH, as these parameters have been identified as having a significant impact on the process. The formation of the products and any by-products is analyzed using gas chromatography (GC) and 19F nuclear magnetic resonance spectroscopy (NMR).
View Article and Find Full Text PDFOrg Lett
December 2024
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China.
We have developed a glycosyl radical-based synthesis of -alkyl glycosides through a deoxygenative Giese addition-reduction-cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of -alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.
View Article and Find Full Text PDFChemistry
December 2024
University of Liverpool, Department of Chemistry, Oxford Street, L69 7ZD, Liverpool, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The Zincke reaction and Birch reduction have been one of the few reactions that allow for ring opening of pyridines ever since the discovery of pyridine more than a century ago. This paper presents a new addition to the list of pyridine ring-opening reactions, reductive Zincke reaction, which affords saturated δ-amino ketones. Under the catalysis of a simple rhodium complex, pyridinium salts with diverse substituents are reduced with formic acid, ring-opened with water, transaminated with a secondary amine and further reduced to afford a wide range of δ-amino ketones, including those in which the alkane chain of the ketones is selectively deuterated or fluorinated.
View Article and Find Full Text PDFChemSusChem
December 2024
JiangXi University of Science and Technology, 156 Ke Jia Avenue,, Ganzhou, CHINA.
Benzothiadiazole (BT) has shown promising applications in fullerene solar cells. However, few BT-based polymer donors exhibited a noticeable power conversion efficiency (PCE) for the fused-ring small molecular acceptor-based polymer solar cells (PSCs). Herein, we developed a D-A (D: donor, A: acceptor) polymer donor F-1 based on fluorinated BT (ffBT) as A unit and chlorinated benzo [1,2-b:4,5-b'] dithiophene (BDT-2Cl) as D unit.
View Article and Find Full Text PDFJ Fluoresc
December 2024
Centre for Nano and Material Sciences, Jain (Deemed-to-be) University, Jain Global Campus, Ramanagaram, Bangalore, 562112, Kanakpuram, Karnataka, India.
In this study, a series of new methoxy ester functionalized core fluorinated, chloro-fluorinated azobenzene derivatives were synthesized. The molecular structures of the azobenzene derivatives (3a-3c and 4a-4c) were confirmed through various analytical methods, with variations in the alkoxy chain length on one end of the aromatic ring. Optical absorption studies of 3a, 3b revealed π-π* transitions around 368-392 nm.
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