169899-58-5Relevant academic research and scientific papers
Novel coumarin-thiazolyl ester derivatives as potential DNA gyrase Inhibitors: Design, synthesis, and antibacterial activity
Cheng, Xiang,Chu, Zhi-Wen,Hu, Rui,Liu, Hao,Lv, Xian-Hai,Xia, Dong-Guo
, (2020)
The design and synthesis of novel coumarin-thiazolyl ester derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activity against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8p exhibited excellent antibacterial activity against four bacteria strains with MIC values of 0.05, 0.05, 8, and 0.05 μg/mL, respectively. In vitro drug-resistant bacterial inhibition experiments indicated that compound 8p exhibited the best bacteriostatic effect in the selected compounds and four positive control drugs with MIC values of 4 μg/mL. In vitro enzyme inhibitory assay showed that compound 8p exhibited potent inhibition against DNA gyrase with IC50 values of 0.13 μM. The molecular docking model indicated that compounds 8p can bind well to the DNA gyrase by interacting with amino acid residues. This study demonstrated that the compound 8p can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.
NHC-Stabilized Radicals in the Formal Hydroacylation Reaction of Alkynes
Phan, Jenny,Ruser, Stephanie-M.,Zeitler, Kirsten,Rehbein, Julia
supporting information, p. 557 - 561 (2018/11/23)
Mechanistic details of transformations catalyzed by N-heterocyclic carbenes (NHC) are currently of great interest, targeting questions on the active catalyst in operation and the structure and reactivity of key intermediates. These mechanistic studies are
Coumarin derivative as - well as preparation method and application thereof (by machine translation)
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Paragraph 0037; 0040, (2020/01/03)
The coumarin-thiazole ester derivative has a broad-spectrum antibacterial activity, and the coumarin,thiazole ester derivative has, a broad-spectrum antibacterial activity, so that 4 the coumarin 7-thiazole, ester derivative has a DCC, DMAP, broad 0 °C-spectrum 10 - 15 antibacterial activity, and the application is a novel antibacterial, agent developed with coumarin-thiazole ester, derivatives as active ingredients 24. (by machine translation)
Structures and reactivities of O-methylated Breslow intermediates
Maji, Biplab,Mayr, Herbert
supporting information, p. 10408 - 10412 (2012/11/07)
As close as you can get: Since Breslow intermediates usually exist in their keto form, their O-protected tautomers may be considered as their closest isolable relatives. A series of these compounds have been synthesized, their structures determined, and the kinetics of their reactions with electrophiles investigated. Copyright
Thiazolium-catalyzed additions of acylsilanes: A general strategy for acyl anion addition reactions
Mattson, Anita E.,Bharadwaj, Ashwin R.,Zuhl, Andrea M.,Scheidt, Karl A.
, p. 5715 - 5724 (2007/10/03)
A strategy utilizing N-heterocyclic carbenes (NHCs) derived from thiazolium salts has been developed for the generation of carbonyl anions from acylsilanes. Synthetically useful 1,4-diketones and N-phosphinoyl-α- aminoketones have been prepared in good to excellent yields via NHC-catalyzed additions of acylsilanes to the corresponding α,β-unsaturated systems and N-phosphinoylimines. These organocatalytic reactions are air- and water-tolerant methods to execute robust carbonyl anion addition reactions. Additionally, polysubstituted aromatic furans and pyrroles have been efficiently synthesized in a one-pot process using this carbonyl anion methodology. The addition of alcohols to the reaction renders the process catalytic in thiazolium salt. In an effort to synthesize a potential intermediate along the proposed reaction pathway, silylated thiazolium carbinols have been identified to provide good yields of carbonyl anion addition products when subjected to the standard reaction conditions in the presence of suitable electrophiles.
Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination
Mattson, Anita E.,Zuhl, Andrea M.,Reynolds, Troy E.,Scheldt, Karl A.
, p. 4932 - 4933 (2007/10/03)
The direct nucleophilic acylation of nitroalkenes is reported utilizing a fluoride-initiated rearrangement of protected thiazolium carbinols. The key combination of fluoride anion and thiourea accesses carbonyl anion reactivity without the use of amine or
Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones
Mattson, Anita E.,Scheidt, Karl A.
, p. 4363 - 4366 (2007/10/03)
(Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.
Kinetics of C(2α)-proton abstraction from 2-benzylthiazolium salts leading to enamines relevant to catalysis by thiamin-dependent enzymes
Barletta, Gabriel L.,Zou, Yu,Huskey, W. Phillip,Jordan, Frank
, p. 2356 - 2362 (2007/10/03)
The kinetics of proton transfer from the C(2α) position of 2-(1-methoxybenzyl)thiazolium salts was studied for the p-H and p-N(CH3)3+ derivatives as models for the protonation of the enamine/C(2α)-carbanion, a key intermed
