Mono- and di-N-alkylated derivatives of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucose (alkyl=methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl) were synthesised by the reductive alkylation of per-O-acetyl-d-glucosamine. (N-ethyl, N-propyl, N-butyl, N-pentyl and N-hexyl)-1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucoses were deacetylated in order to attempt an enzymatic phosphorylation. All products were characterised by means of IR, NMR and MS spectra. N-Ethyl- and N-pentyl-d-glucosamines were found to exhibit weak antifungal activity.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1016/j.carres.2005.05.013 | DOI Listing |
Materials (Basel)
December 2024
Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Skłodowska Str., 41-819 Zabrze, Poland.
Phenothiazine-based photosensitizers bear the intrinsic potential to substitute various expensive organometallic dyes owing to the strong electron-donating nature of the former. If coupled with a strong acceptor unit and the length of N-alkyl chain is appropriately chosen, they can easily produce high efficiency levels in dye-sensitized solar cells. Here, three novel D-A dyes containing 1H-tetrazole-5-acrylic acid as an acceptor were synthesized by varying the N-alkyl chain length at its phenothiazine core and were exploited in dye-sensitized solar cells.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
ConspectusSelective chemical modification of endogenous proteins in living systems with synthetic small molecular probes is a central challenge in chemical biology. Such modification has a variety of applications important for biological and pharmaceutical research, including protein visualization, protein functionalization, proteome-wide profiling of enzyme activity, and irreversible inhibition of protein activity. Traditional chemistry for selective protein modification in cells largely relies on the high nucleophilicity of cysteine residues to ensure target-selectivity and site-specificity of modification.
View Article and Find Full Text PDFACS Chem Neurosci
December 2024
Designer Drug Research Unit, National Institute on Drug Abuse, Intramural Research Program, Baltimore, Maryland 21224, United States.
5-methoxy-,-dimethyltrytpamine (5-MeO-DMT) analogs are used as recreational drugs, but they are also being developed as potential medicines, warranting further investigation into their pharmacology. Here, we investigated the neuropharmacology of 5-MeO-DMT and several of its -alkyl, -allyl, and 2-methyl analogs, with three major aims: 1) to determine in vitro receptor profiles for the compounds, 2) to characterize in vitro functional activities at serotonin (5-HT) 2A receptors (5-HT) and 1A receptors (5-HT), and 3) to examine the influence of 5-HT on 5-HT-mediated psychedelic-like effects in the mouse head twitch response (HTR) model. In vitro receptor binding and functional assays showed that all 5-MeO-DMT analogs bind with high affinity and activate multiple targets (e.
View Article and Find Full Text PDFRapid Commun Mass Spectrom
January 2025
Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, CNRS, Paris, France.
Rationale: The mechanism underlying dopant-assisted atmospheric pressure photoionization's (APPI) formation of ions is unclear and still under debate for many chemical classes. In this study, we reexamined the gas-phase reaction mechanisms responsible for the generation of [M-H] precursor ions, resulting from the loss of a single hydrogen atom, in a series of N-alkyl-substituted thieno[3,4-c]-pyrrole-4,6-dione (TPD) derivatives.
Methods: Atmospheric pressure photoionization combined with higher order MS/MS using high-resolution mass spectrometry (APPI-HR-CID-MS) and electronic structure calculations using density functional theory were used to determine the chemical structure of observed [M-H] ions.
RSC Adv
November 2024
Department of Natural Products, College of Clinical Pharmacy, Imam Abdulrahman Bin Faisal University Dammam 1982 Saudi Arabia.
We have designed 17 new 2-oxo-3-phenylquinoxalines the chemoselective Michael reaction of 3-phenylquinoxalin-2(1)-one with acrylic acid derivatives. The ester, ethyl 3-(2-oxo-3-phenylquinoxalin-1(2)-yl)propanoate, was reacted with hydroxylamine and hydrazine to produce -hydroxy-3-(2-oxo-3-phenylquinoxalin-1(2)-yl)propanamide and hydrazide, respectively. Further modifications were made through reactions with isothiocyanates and azide coupling with amines, yielding thiosemicarbazides and -alkyl derivatives.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!