For the first time, a method for enantiomer resolution of the anticonvulsant Galodif (1-((3-chlorophenyl)(phenyl)methyl) urea) by chiral HPLC was developed, whereas the enantiomeric composition of 1-((3-chlorophenyl)(phenyl)methyl) amine-precursor in Galodif synthesis-cannot be resolved by this method. However, starting 1-((3-chlorophenyl)(phenyl)methyl) amine quantitatively forms diastereomeric N-((3-chlorophenyl)(phenyl)methyl)-1-camphorsulfonamides in reaction with chiral (1R)-(+)- or (1S)-(-)-camphor-10-sulfonyl chlorides. The diastereomeric ratio of obtained camphorsulfonamides can be easily determined by NMR H and C spectroscopy. The DFT calculations of specific rotation of Galodif enantiomers showed good agreement with experimental data. The absolute configuration of enantiomers was proposed for the first time.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chir.23005 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Supramolecular Entrapping and Extraction of Selenate, Molybdate and Tungstate Ions from Water by Nanojars.
Inorg Chem
January 2025
Department of Chemistry, Western Michigan University, Kalamazoo, Michigan 49008, United States.
The supramolecular binding exclusively by H-bonds of SeO, MoO and WO ions to form nanojars of the formula [EO⊂{-Cu(μ-OH)(μ-pz)}] (; E = Se, Mo, W; = 28-34; pz = pyrazolate) was studied in solution by electrospray ionization mass spectrometry, variable temperature, paramagnetic H NMR and UV-vis spectroscopy, and in the solid state by single-crystal X-ray crystallography. These large anions allow for the observation of a record nanojar size, (E = Mo, W). Six crystal structures are described of nanojars of varying sizes with either SeO, MoO or WO entrapped ions, including the first example of a cocrystal of two different nanojars in crystallographically unique positions, and .
View Article and Find Full Text PDFDegradable Theranostic Polyurethane for Macrophage-Targeted Antileishmanial Drug Delivery.
Biomacromolecules
January 2025
Polymer Research Centre and Centre for Advanced Functional Materials, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Nadia, Mohanpur 741246, West Bengal, India.
The present investigation aims to develop a reactive oxygen species (ROS) and esterase-responsive biodegradable mannosylated polyurethane to effectively deliver the encapsulated antileishmanial drug amphotericin B (AmB) selectively to infected macrophage cells. Owing to suitable amphiphilic balance, the as-synthesized glycosylated polyurethane () with aryl boronic ester-based diol () moiety as ROS-trigger, water-soluble mannose pendants, and fluorescent 4,4-difluoro-4-bora-3a,4a-diaza--indacene (BODIPY) chain ends for bioimaging formed nanoaggregates in an aqueous medium as confirmed by H NMR spectroscopy, dynamic light scattering (DLS), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), and critical aggregation concentration (CAC) measurements. Aided by two endogenous stimuli present in phagolysosome, ROS and esterase, AmB-encapsulated polymeric nanoaggregates as drug delivery vehicles achieved an efficient reduction of both and intracellular amastigote burden compared to the free AmB.
View Article and Find Full Text PDFThiol-Ene Click Chemistry: A General Strategy for Tuning the Properties of Vinylene-Linked Covalent Organic Frameworks.
ACS Appl Mater Interfaces
January 2025
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, China.
Vinylene-linked Covalent Organic Frameworks (V-2D-COFs) are a class of promising porous organic materials that feature fully π-conjugated structures, high crystallinity, ultrahigh chemical stability, and extraordinary optoelectronic properties. However, the types of reactions and the availability of monomers for synthesizing linked COFs are considerably limited by the irreversibility of the C═C bond, and the complete π-conjugated structure restricts their in-depth research in hydrophilicity, membrane materials, and proton conductivity. Postsynthetic modification (PSM), which can avoid these problems by incorporating functional moieties into the predetermined framework, provides an alternative way to construct diverse V-2D-COFs.
View Article and Find Full Text PDFBasic Science and Pathogenesis.
Alzheimers Dement
December 2024
Huashan Hospital, Fudan University, Shanghai, China.
Background: Identifying circulating metabolites associated with dementia, cognition, and brain volume may improve the understanding of dementia pathogenesis and provide novel insights for preventive and therapeutic interventions.
Method: This cohort study included a total of 87,885 participants (median follow-up 9.1 years, 54% female) without dementia at baseline from the UK Biobank.
Cationic -Tricarbollide μ-10,11-H-10,11-H-7-MeN--7,8,9-CBH and Its Halogenated Derivatives: The Slow Iodination Process Occurring through Cationic Iodonium Tricarbollides.
Inorg Chem
January 2025
Institute of Inorganic Chemistry, Czech Academy of Sciences, CZ, 250 68 Husinec-Řež, Czech Republic.
A series of -tricarbollides based on 10,11-X-7-MeN--7,8,9-CBH (X = H, Cl, Br, I) and their protonated, i.e. cationic, counterparts, which have an extra H-bridge over the B10-B11 vector in the open pentagonal belt, were prepared.
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!