Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The naphthalene sulfonamide scaffold is known to possess CCR8 antagonistic properties. In order to expand the structure-activity relationship study of this compound class, a variety of palladium-catalyzed cross-coupling reactions was performed on a bromo-naphthalene precursor yielding a diverse library. These compounds displayed CCR8 antagonistic properties in binding and calcium mobilization assays, with IC values in the 0.2 - 10 µM range. The decreased activity, when compared to the original lead compound, was rationalized by homology molecular modeling.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.bioorg.2020.104560 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Mechanistic Organometallic Studies Drive Reagent Selection and Catalyst Design for the Palladium-Catalyzed Trifluoromethylthiolation of Aryl Electrophiles.
Organometallics
June 2025
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48104, United States.
This article describes a detailed investigation of the palladium-catalyzed coupling of aryl (pseudo)halides (ArX) with MSCF to form aryl trifluoromethylthioethers (ArSCF). Mechanistic organometallic studies are used to interrogate two key elementary steps of the catalytic cycle: (1) transmetalation of Pd(Ar)(X) complexes with MSCF and (2) Ar-SCF bond-forming reductive elimination. These studies reveal that tetramethylammonium trifluoromethylthiolate, NMeSCF, exhibits a combination of fast kinetics and high chemoselectivity for transmetalation.
View Article and Find Full Text PDFA Convenient, Pd-Free Approach to the Synthesis of Risdiplam.
Molecules
August 2025
Medicinal Biotechnology Department, Sirius University of Science and Technology, Olimpiyskiy Ave. 1, 354340 Sirius, Krasnodar Region, Russia.
Several approaches to the synthesis of risdiplam, a pharmacologically relevant pyridopyrimidinone derivative, have been recently reported. However, most of these routes rely exclusively on palladium-catalyzed, cross-coupling reactions and involve low-yielding intermediates, which limit their scalability and complicate impurity control. In this work, we present a five-step, straightforward route to risdiplam, utilizing ethyl 2,8-dimethylimidazo[1,2-]pyridazine-3-carboxylate-an accessible and cost-effective building block previously developed by our research group-as a starting material.
View Article and Find Full Text PDFPalladium-Catalyzed Decarboxylative Cross-Coupling of 2,4-Dienoic Acids and Aryl Halides: Access to Fluorescence Active ()-1,4-Diarylbutadienes.
J Org Chem
August 2025
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Botanic Garden, Howrah 711103, India.
A range of (,)-1,4-diarylbutadienes has been efficiently achieved through a Pd-catalyzed decarboxylative cross-coupling of various 2,4-dienoic acids with diverse (hetero)aryl halides, such as bromides, chlorides, and iodides. This protocol successfully produces the corresponding 1,4-diarylbutadiene cross-coupled products in high yields across a large range of substrates (68 examples), demonstrating compatibility with various sensitive functional groups, including heterocycles. A catalytic amount of silver salt was used as a cocatalyst in this approach, replacing the stoichiometric amounts utilized in earlier reports.
View Article and Find Full Text PDFRapid construction of furan-linked bisheterocycles a palladium-catalyzed domino Heck/cross-coupling reaction.
Org Biomol Chem
August 2025
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, China.
A palladium-catalyzed domino Heck/cross-coupling reaction of alkene-tethered aryl iodides with β-chloroenones is reported. This reaction enables the formation of one C-O bond and two C-C bonds to construct bisheterocycles in a single operation an intramolecular carbopalladation, followed by a carbene-based cross-coupling with β-chloroenones as a non-diazo carbene precursor, providing an efficient method for synthesizing furan-linked dihydrobenzofurans/oxindoles in yields up to 98%.
View Article and Find Full Text PDFPd-Catalyzed One-Pot Synthesis of Indole-3-carboxylic Acids via a Sequential Water-Mediated Nucleophilic Addition to Amides/Esters and Carbon-Heteroatom Cross-Coupling Reaction Strategy.
J Org Chem
August 2025
College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040, P. R. China.
Using 4-bromoindole-3-carboxylic acid derivatives (amides or esters) as substrates, this paper successfully developed a trace water-promoted, palladium-catalyzed "one-pot" reaction strategy for synthesizing 4-amino/alkoxyindole-3-carboxylic acid products. With PdCl (5 mol %) as the precatalyst, Xantphos as the ligand, and cesium pivalate as the additive, this synthetic method innovatively integrates nucleophilic substitution of amides/esters with Pd-catalyzed C-N or C-O cross-coupling into a single reaction system, achieving efficient synergy of multistep transformations. This approach facilitates a modular and rapid assembly of multisubstituted indole-3-carboxylic acids, exhibiting broad functional group compatibility while maintaining good reaction yields.
View Article and Find Full Text PDF