A late-stage amination of a bifunctional dihydroxanthene (DHX) scaffold is reported to access a wide variety of new near-infrared (NIR) chromophores/fluorophores. The divergent approach allows the coupling of aliphatic and aromatic amines and readily provides molecular diversity shedding light on the structure-fluorescence relationship of this emerging class of NIR fluorophores.
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http://dx.doi.org/10.1021/acs.orglett.6b02564 | DOI Listing |
Neuropsychiatr Dis Treat
December 2024
Department of Medicine and Surgery, Kore University of Enna, Enna (EN), Italy.
Background: Currently available antipsychotics, mainly targeting the dopaminergic pathway, fail to address the complexity of schizophrenic symptoms and can lead to burdening adverse events. The need for innovative pharmacological options remains critical and research is now focusing on the development of non-dopaminergic antipsychotics. This review aims to summarize the current literature on the most promising non-dopaminergic new APs (muscarinic agonists, Trace Amine Associated Receptor 1 agonists, Glycine Transporter Type 1 inhibitors and 5-HT2A antagonists) and provide a clinically oriented overview of their efficacy, safety and potential use in schizophrenia.
View Article and Find Full Text PDFOrg Lett
December 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
We here report an efficient DNA-compatible furan-thiol-amine reaction for macrocyclization and late-stage amine transformation. This reaction, conducted under mild conditions, enables the facile cyclization of DNA-conjugated linear peptides into thiopyrrole-grafted macrocycles regardless of ring size or side-chain modification with good to excellent conversion yields. Additionally, this strategy was employed for the late-stage transformation of terminal amines, serving as critical intermediates in the construction of DNA-encoded peptide libraries.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
Herein, we report a sustainable and efficient method for the synthesis of structurally diverse phthalimidines from 2-formylbenzoic acid and primary amines using an iridium-catalyzed reductive lactamization strategy. The advantages of this method, such as the use of water-ethanol as a solvent, broad substrate scope, high catalyst efficiency (/ up to 10000), good scalability, and easy purification, enable it to be a practical approach to phthalimidines. It is suggested that iridium hydride formation is involved in the rate-limiting step.
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 PDFJ Am Chem Soc
December 2024
Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Genetically encoded libraries (GEL) are increasingly being used for the discovery of ligands for "undruggable" targets that cannot be addressed with small molecules. Foundational GEL platforms like phage-, yeast-, ribosome-, and mRNA-display have enabled the display of libraries composed of 20 natural amino acids (20AA). Unnatural amino acids (UAA) and chemical post-translational modification (cPTM) expanded GEL beyond the 20AA space to yield unnatural linear, cyclic, and bicyclic peptides.
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