A series of 153 derivatives of 3-phenyl-2H-benzoxazine-2,4(3H)-dione substituted in position 6 or 7 on benzoxazine and on the phenyl ring was synthesized. The compounds were evaluated in vitro for antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. The activity of the compounds increases with increasing hydrophobicity and electron-withdrawing properties of the substituents on the phenyl ring, whereas the effect of the substituents on the benzoxazine ring seems to be more complex.
Download full-text PDF |
Source |
|---|
Publication Analysis
Top Keywords
Similar Publications
Antistaphylococcal Triazole-Based Molecular Hybrids: Design, Synthesis and Activity.
Pharmaceuticals (Basel)
January 2025
Department of Microbiology, Virology and Immunology, I. Horbachevsky Ternopil State Medical University, 46001 Ternopil, Ukraine.
Background: In the era of resistance, the design and search for new "small" molecules with a narrow spectrum of activity that target a protein or enzyme specific to a certain bacterium with high selectivity and minimal side effects remains an urgent problem of medicinal chemistry. In this regard, we developed and successfully implemented a strategy for the search for new hybrid molecules, namely, the not broadly known [2-(3-R-1-[1,2,4]-triazol-5-yl)phenyl]amines. They can act as "building blocks" and allow for the introduction of certain structural motifs into the desired final products in order to enhance the antistaphylococcal effect.
View Article and Find Full Text PDFConjugation of Short-Chain Fatty Acids to Bicyclic-Amines for Analysis by Liquid Chromatography Tandem Mass Spectroscopy.
Molecules
January 2025
Blood and Shock Research, US Army Institute of Surgical Research, JBSA Fort Sam Houston, San Antonio, TX 78234, USA.
Conjugation of short-chain fatty acids (SDFAs) to amines containing ring structures allows for better measurement by liquid chromatography tandem mass spectroscopy (LC-MS/MS). However, collision-induced dissociation (CID) results in breaking the conjugate back to the original SCFA and amine. We therefore set out to find an amine that would remain on the SCFA after CID and create a unique daughter for selectivity of measurement.
View Article and Find Full Text PDFSynthesis and Biological Evaluation of New -Restricted Triazole Analogues of Combretastatin A-4.
Molecules
January 2025
Department of Organic Chemistry, University of Valencia, E-46100 Burjassot, Spain.
The natural products combretastatins A-1 and A-4 are potent antimitotic and vascular-disrupting agents through their binding at the colchicine site in tubulin. However, these compounds suffer from a low water solubility and a tendency to isomerize to the inactive stilbenes. In this study, we have prepared a series of 18 -restricted triazole analogues of combretastatin A-4 (CA-4), maintaining, in all cases, the 3,4,5-trimethoxy phenyl ring A, with the aim of investigating the substitution pattern on the B-ring in a systematic way.
View Article and Find Full Text PDFBenzo-Fused Phosphepines: Synthesis by Gold(I)-Catalyzed Intramolecular Hydroarylation and Ring Inversion.
Chemistry
January 2025
Osaka Metropolitan University: Osaka Koritsu Daigaku, Chemistry, 3-3-138 Sugimoto, Sumiyoshi-ku, 558-8585, Osaka, JAPAN.
Gold(I)-catalyzed intramolecular hydroarylation of dialkynyl(biaryl)phosphine oxides provided versatile benzo-fused phosphepine oxides. O-exo adducts were obtained as the major product, and O-endo adducts were the minor product. O-exo and O-endo indicate the position of an oxygen atom with respect to the central phosphepine framework.
View Article and Find Full Text PDFFacile synthesis of unknown 6,7-dihydrofuro[3,4-]pyridines and 3,4-diaryloylpyridines from -homopropargylic β-enaminones.
Org Biomol Chem
January 2025
Department of Chemistry, Faculty of Arts and Science, Middle East Technical University, 06800 Ankara, Turkey.
In this paper, we have uncovered a new reaction of -homopropargylic β-enaminones, -(4-phenyl-3-butynyl)-β-enaminones. When subjected to a reaction with excess molecular iodine or -iodosuccinimide in the presence of cesium carbonate, -homopropargylic β-enaminones afford 6,7-dihydrofuro[3,4-]pyridines in low to moderate yields. The generation of two new C/O-C bonds during the reaction leads to the construction of unknown heterobicyclic 5,6-fused ring systems.
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!