83507-73-7Relevant academic research and scientific papers
Novel 3-Aminothiazolquinolones: Design, Synthesis, Bioactive Evaluation, SARs, and Preliminary Antibacterial Mechanism
Cui, Sheng-Feng,Addla, Dinesh,Zhou, Cheng-He
, p. 4488 - 4510 (2016/06/13)
A series of novel 3-aminothiazolquinolones as analogues of quinolone antibacterial agents were designed and synthesized in an effort to circumvent quinolone resistance. Among these 3-aminothiazolquinolones, 3-(2-aminothiazol-4-yl)-7-chloro-6-(pyrrolidin-1-yl) quinolone 12b exhibited potent antibacterial activity, low cytotoxicity to hepatocyte cells, strong inhibitory potency to DNA gyrase, and a broad antimicrobial spectrum including against multidrug-resistant strains. This active molecule 12b also induced bacterial resistance more slowly than norfloxacin. Analysis of structure-activity relationships (SARs) disclosed that the 2-aminothiazole fragment at the 3-position of quinolone plays an important role in exerting antibacterial activity. Molecular modeling and experimental investigation of aminothiazolquinolone 12b with DNA from a sensitive methicillin-resistant Staphylococcus aureus (MRSA) strain revealed that the possible antibacterial mechanism might be related to the formation of a compound 12b-Cu2+-DNA ternary complex in which the Cu2+ ion acts as a bridge between the backbone of 3-aminothiazolquinolone and the phosphate group of the nucleic acid.
New reactivity of nitropyrimidinone: Ring transformation and N-C transfer reactions
Nishiwaki, Nagatoshi,Matsushima, Kazuo,Chatani, Miki,Tamura, Mina,Ariga, Masahiro
, p. 703 - 707 (2007/10/03)
Nitropyrimidinone 1 revealed new reactivity upon treatment with active methylene compounds 2 under basic conditions. The N1-C2-C3-C4 moiety of 1 combined with two carbon units of 2 affording polyfunctionalized pyridones 4, which was hitherto unknown ring transformation. On the other hand, the N1-C2 moiety of 1 was transferred to the methylene group of 2 giving functionalized enamines 3. It was also possible to modify the amino group in 3a by reactions with primary amines. Enamines 3 reacted with hydrazines, and leading to functionalized pyrazoles 7 quantitatively. The ratios of regioisomeric pyrazoles 7/8 were moderately controlled by use of sterically hindered enamines 3h, 3k and 31. Furthermore, enamine 3a was readily converted to 1,4-diazepines 9 having a functional group at the 6-position.
