Isolation of a dihalogen molecule XY (XY=Cl2, Br2, or BrCl) with CS2 in a solid Ar matrix at about 15 K leads, by broad-band UV-vis photolysis (200
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Catalytic asymmetric C-N cross-coupling towards boron-stereogenic 3-amino-BODIPYs.
Nat Commun
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong, China.
3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, the synthesis of chiral 3-amino-BODIPYs, particularly the catalytic asymmetric version, remains a challenge. Herein, we report the synthesis of boron-stereogenic 3-amino-BODIPYs via a palladium-catalyzed desymmetric C-N cross-coupling of prochiral 3,5-dihalogen-BODIPYs.
View Article and Find Full Text PDFThe Relationship Between Spin Crossover (SCO) Behaviors, Cation and Ligand Motions, and Intermolecular Interactions in a Series of Anionic SCO Fe(III) Complexes with Halogen-Substituted Azobisphenolate Ligands.
Molecules
November 2024
Department of Chemistry, Graduate School of Science, Kobe University, 1-1, Rokkodai-cho, Nada-ku, Kobe 657-8501, Hyogo, Japan.
To investigate the halogen substitution effect on the anionic spin crossover (SCO) complexes, azobisphenolate ligands with 5,5'-dihalogen substituents from fluorine to iodine were synthesized, and their anionic Fe complexes , , , and were isolated. The temperature dependence of magnetic susceptibility and crystal structure revealed that , , and are all isostructural and exhibit SCO with the rotational motion of the cation and ligands, whereas shows incomplete SCO. Note that and showed irreversible and reversible cooperative SCO transitions, respectively.
View Article and Find Full Text PDFVisible-Light-Mediated Vicinal Dihalogenation of Unsaturated C-C Bonds Using Dual-Functional Group Transfer Reagents.
J Am Chem Soc
November 2024
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
The growing demand for chemical production continues to drive the development of sustainable and efficient methods for introducing molecular complexity. In this context, the exploration of unconventional functional group transfer reagents (FGTRs) has led to significant advancements in practical and atom-efficient synthetic protocols. Aiming to advance the field of valuable organic synthesis, herein we report the successful development of carbon-based, bench-stable, modular, and inexpensive reagents implemented in dual halogen transfer to unsaturated hydrocarbons via photocatalytic activation of reagents based on a radical-polar crossover mechanism.
View Article and Find Full Text PDFβ-Carboline-3-carboxamide Antimalarials: Structure-Activity Relationship, ADME-Tox Studies, and Resistance Profiling.
ACS Infect Dis
November 2024
Department of Chemistry and Virginia Tech Center for Drug Discovery, Virginia Tech, 1040 Drillfield Drive, Blacksburg, Virginia 24061, United States.
The development of parasite resistance to both artemisinin derivatives and their partner drugs jeopardizes the effectiveness of the artemisinin combination therapy. Thus, the discovery of new antimalarial drugs, with new mechanisms of action, is urgently needed. We recently disclosed that β-carboline was orally efficacious in -infected mice and that it showed low cross-resistance between susceptible and four different drug-resistant strains.
View Article and Find Full Text PDFSynthesis and evaluation of isothiazolo[4,5-]pyridines as cyclin G-associated kinase (GAK) inhibitors.
Org Biomol Chem
September 2024
KU Leuven, Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, Herestraat 49, box 1043, 3000 Leuven, Belgium.
Isothiazolo[4,3-]pyridines have been extensively explored as inhibitors of cyclin G-associated kinase (GAK). In order to expand the structure-activity relationship study and to discover other chemotypes that act as GAK inhibitors, the closely related isothiazolo[4,5-]pyridine scaffold was explored. An easy and efficient synthetic procedure to access 3,5- and 3,6-dihalogenated isothiazolo[4,5-]pyridines as key building blocks was developed.
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