The title compound, C(12)H(13)NO(2), represents a conformationally restricted 2-pyridone analogue of 1,4-dihydro-pyridine-type calcium antagonists and was selected for a crystal structure determination in order to explore some aspects of drug-receptor inter-action. In the mol-ecule, two stereogenic centres are of opposite chirality, whereas a racemate occurs in the crystal. It was found that the formally aminic N atom of the heterocycle is essentially sp(2)-hybridized with the lone-pair electrons partially delocalized through conjugation with the adjacent carbonyl bond. As a result, the central pyridone ring assumes an unsymmetrical half-chair conformation. The critical 4-phenyl ring is fixed in a pseudo-axial and perpendicular orientation [dihedral angle 85.8 (1)°] with respect to the pyridone ring via an oxygen bridge. In the crystal a pair of centrosymmetric N-H⋯O hydrogen bonds connect mol-ecules of opposite chirality into a dimer. The dimers are packed by hydrophobic van der Waals inter-actions.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979478 | PMC |
| http://dx.doi.org/10.1107/S1600536810017848 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Discovery and Synthetic Applications of a NAD(P)H-Dependent Reductive Aminase from .
ACS Catal
January 2025
Department of Biotechnology, Delft University of Technology, van der Maasweg 9, 2629 HZ Delft, The Netherlands.
Reductive amination is one of the most synthetically direct routes to access chiral amines. Several Imine Reductases (IREDs) have been discovered to catalyze reductive amination (Reductive Aminases or RedAms), yet they are dependent on the expensive phosphorylated nicotinamide adenine dinucleotide cofactor NADPH and usually more active at basic pH. Here, we describe the discovery and synthetic potential of an IRED from (RedAm) that catalyzes reductive amination between a series of medium to large carbonyl and amine compounds with conversions of up to >99% and 99% enantiomeric excess at neutral pH.
View Article and Find Full Text PDFSelection of a Fluorinated Aptamer Targeting the Viral RNA Frameshift Element with Different Chiralities.
Biochemistry
January 2025
Department of Biochemistry and Molecular Biology, Melvin and Bren Simon Cancer Center, Indiana University School of Medicine, Indianapolis, Indiana 46202, United States.
The development of RNA aptamers with high specificity and affinity for target molecules is a critical advancement in the field of therapeutic and diagnostic applications. This study presents the selection of a 2'-fluoro-modified mirror-image RNA aptamer through the in vitro SELEX process. Using a random RNA library, we performed iterative rounds of selection and amplification to enrich aptamers that bind specifically to the viral attenuator hairpin RNA containing the opposite chirality, which is an important part of the frameshift element.
View Article and Find Full Text PDFImpact of Structural Subtleties on Chirality Induction and Amplification in Trizinc(II)porphyrin Trimers.
Chemistry
January 2025
Indian Institute of Technology Kanpur, Department of Chemistry, Kanpur, 208016, Kanpur, INDIA.
Herein, we report the precise control of molecular to supramolecular chirality induction at the single-molecule level just upon subtle modification in an achiral 'nano-size' trizinc(II) porphyrin trimer. A slight variation in the projection of the substituent at the periphery of the central porphyrin unit in a porphyrin trimer (host) resulted in pronounced changes in the interchromophoric arrangement, leading to distinct 'open' and 'closed' conformations. While 'open' form generates 'monomeric' complex with low CD amplitude, 'closed' form produces exclusive 'polymer' with large, amplified CD signal with opposite sign due to stronger intermolecular excitonic coupling.
View Article and Find Full Text PDFMagnetic topological Weyl fermions in half-metallic InCoSe.
J Phys Condens Matter
January 2025
Qingdao Institute for Theoretical and Computational Sciences, School of Chemistry and Chemical Engineering, Shandong University, Qingdao 266237, People's Republic of China.
Magnetic Weyl semimetals (WSMs) have recently attracted much attention due to their potential in realizing strong anomalous Hall effects. Yet, how to design such systems remains unclear. Based on first-principles calculations, we show here that the ferromagnetic half-metallic compound InCoSehas several pairs of Weyl points and is hence a good candidate for magnetic WSM.
View Article and Find Full Text PDFCatalytic Enantioselective Nucleophilic Amination of α-Halo Carbonyl Compounds with Free Amines.
J Am Chem Soc
January 2025
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
Catalytic enantioselective substitution of the readily available racemic α-halo carbonyl compounds by nitrogen nucleophiles represents one of the most convenient and direct approaches to access enantioenriched α-amino carbonyl compounds. Distinct from the two available strategies involving radicals and enolate ions, herein we have developed a new protocol featuring an electronically opposite way to weaken/cleave the carbon-halogen bond. A suitable chiral anion-based catalyst enables effective asymmetric control over the key positively charged intermediates.
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!