Cultures of Umbelopsis ramanniana (=Mucor ramannianus) were grown in fluid Sabouraud medium for 3 days, dosed with 0.23 mM benzo[f]quinoline, benzo[h]quinoline, or phenanthridine (benzo[c]quinoline), and incubated for another 18 days. Cultures were extracted and metabolites (66-75% of the UV absorbance) were separated by high-performance liquid chromatography. They were identified by mass spectrometry and nuclear magnetic resonance spectroscopy. Benzo[f]quinoline was metabolized to benzo[f]quinoline trans-7,8-dihydrodiol, benzo[f]quinoline N-oxide, and 7-hydroxybenzo[f]quinoline, benzo[h]quinoline was metabolized to benzo[h]quinoline trans-5,6-dihydrodiol, benzo[h]quinoline trans-7,8-dihydrodiol, and 7-hydroxybenzo[h]quinoline, and phenanthridine was metabolized to phenanthridine N-oxide and phenanthridin-6(5H)-one. At least one of the metabolites produced from each compound was mutagenic and could not be considered detoxified.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1007/s00253-004-1738-8 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Polysubstituted Benzo[][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles.
Org Lett
January 2025
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China.
Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.
View Article and Find Full Text PDFSynthesis, in vivo evaluation, and in silico molecular docking of benzo[h]quinoline derivatives as potential Culex pipiens L. larvicides.
Bioorg Chem
December 2024
Chemistry Department, Faculty of Science, Ain Shams University, Cairo 11566, Egypt. Electronic address:
A new series of benzo[h]quinoline-containing heterocycles was synthesized via reactions of benzo[h]quinolinyl-2(3H)-furanone with some nitrogen bidentate nucleophiles, leading to the formation of pyridazinone, pyrrolinone, benzimidazole, and benzoxazinone derivatives. The synthesized compounds were evaluated for their insecticidal activity against Culex pipiens L. larvae.
View Article and Find Full Text PDFpH- and Saccharide-Responsive Cyclometalated Iridium(III) Complexes with Boronic Acid Moieties Displaying a Wide Range of Phosphorescence Colors.
Chemistry
December 2024
Waseda University: Waseda Daigaku, Department of Chemistry and Biochemistry, 169-8555, Tokyo, JAPAN.
Single compounds displaying a wide range of luminescent colors are attractive optical materials for sensor applications. In this study, we present the beneficial combination of a cyclometalated iridium(III) complex scaffold and boronic acid units for designing stimuli-responsive luminescent materials with various emission colors. Five iridium(III) complexes bearing a diboronic acid ligand (bpyB2) were synthesized: Ir(C^N)bpyB2 (C^N = 2-phenylpyridine (1), 2-(2,4-difluorophenyl)pyridine (2), 2-(4-methoxyphenyl)pyridine (3), benzo[h]quinoline (4), 1-phenylisoquinoline (5)).
View Article and Find Full Text PDFStructural and optical studies of fluoride ion binding using N-heteroaromatic ligands.
Dalton Trans
December 2024
Department of Industrial and Engineering Chemistry, Institute of Chemical Technology - Indian Oil Odisha Campus, Bhubaneswar, Odisha 751013, India.
8-Hydroxyquinoline and imidazole, two important N-heteroaromatic systems, have a strong affinity towards various anions their acidic OH or NH protons. Three receptor ligands, 5-(1-benzo[]imidazol-2-yl)quinolin-8-ol (1), 5-(benzo[]thiazol-2-yl)quinolin-8-ol (2), and 4-(1-benzo[]imidazol-2-yl)benzene-1,3-diol (3), were synthesized, and their fluoride (F) ion binding properties were investigated. These ligands could selectively bind F ions, and their respective F complexes, namely, 1-TBAF, 2-TBAF, and 3-TBAF (TBAF = tetrabutylammonium fluoride), were characterized using single crystal X-ray analysis, NMR, UV-vis, Hirshfeld surface (HS) analysis and computational studies.
View Article and Find Full Text PDFC(sp2)-H Acylation of benzo[h]quinolines at Room Temperature via Aldehyde Autoxidation and Palladium Catalysis Cooperation.
Chemistry
December 2024
Indian Association for the Cultivation of Science, School of Chemical Sciences, 2A & 2B Raja S. C. Mullick Road, Jadavpur, 700032, Kolkata, INDIA.
Herein, we report Pd-catalyzed C(sp2)-H acylation using aldehyde as acyl source and O2 as the green oxidant at room temperature. A selective association of acyl radical formed in-situ during aldehyde autoxidation with Pd-catalysis is the key to the process. The reaction afforded products in good yields (up to 82%) and it is scalable.
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!