80-65-9Relevant articles and documents
Preparation method and application of 3-amino-2-oxazolidinone derivative
-
Paragraph 0070-0074, (2021/04/10)
The invention discloses a preparation method and application of a 3-amino-2-oxazolidinone derivative. The invention relates to a derivative of a general formula I with a bacterial quorum sensing regulation effect, wherein definitions of substituent groups in the general formula I are described in the specification; a preparation method of the compound of general formula I; a pharmaceutical composition comprising the compound of general formula I; and application of the compound of general formula I in the preparation of medicaments. Biological activity detection is carried out on the compound shown as the general formula I, the regulation effect of the compound shown as the general formula I on bacterial quorum sensing is further proved, an experimental basis is provided for a new strategy for treating diseases caused by drug-resistant gram-negative bacteria, and an important research value is achieved for solving the drug resistance problem.
Synthetic method of furazolidone metabolite AOZ
-
Paragraph 0028; 0033, (2020/07/13)
The invention discloses a preparation method of 3-amino-2-oxazolidinone (AOZ). The method comprises the following steps: 1) carrying out a reaction on ethylene glycol and PBr3 to obtain 2-bromoethanol; 2) in the presence of an alkali, carrying out a reaction on NH2NH2Boc and 2-bromoethanol to obtain Boc protected 2-hydrazinoethanol; 3) in the presence of an alkali, carrying out a reaction on Boc protected 2-hydrazinoethanol and diethyl carbonate to obtain Boc protected 3-amino-2-oxazolidinone; and 4) performing deprotection on the Boc group in the Boc protected 3-amino-2-oxazolidinone to obtain 3-amino-2-oxazolidinone. According to the method, the yield of AOZ in the synthesis process is obviously increased, and separation and purification are facilitated.
Design, synthesis, and biological evaluation of 3-amino-2-oxazolidinone derivatives as potent quorum-sensing inhibitors of Pseudomonas aeruginosa PAO1
Jiang, Kai,Lin, Feng,Wu, Hao,Xiao, Junhai,Xiao, Zijian,Yan, Xinlin,Yu, Jiahao,Yue, Yuandong,Zhao, Meihua,Zhou, Xiaoping
, (2020/03/31)
Due to the increasing resistance of Pseudomonas aeruginosa to most clinically relevant antimicrobials, it is challenging to treat bacterial infection with traditional antibiotics. Quorum sensing can regulate the production of biofilms and virulence factors which are closely related to bacterial resistance. Previously we synthesized a series of oxazolidinone compounds targeting the quorum-sensing transcriptional regulatory protein CviR and ZS-12 showed good activity against Chromobacterium violaceum CV026 quorum-sensing. In this study, eighteen 3-amino-2-oxazolidinone compounds were designed and synthesized using ZS-12 as the lead compound. We initially evaluated the inhibitory activities of novel oxazolidinone compounds against QS using C. violaceum CV026 as a reporter strain. Thirteen compounds showed good activities (IC50 range 3.69–63.58 μM) and YXL-13 inhibition was the most significant (IC50 = 3.686 ± 0.5790 μM) against biofilm formation and virulence factors determination of P. aeruginosa PAO1. In vitro, YXL-13 significantly inhibited the formation of PAO1 biofilm (range 42.98%–17.67%), the production of virulence factors (pyocyanin, elastase, rhamnolipid, and protease), and bacterial motility. Moreover, the combination of YXL-13 with an antibiotic (meropenem trihydrate) could significantly improve the antibiotic susceptibility of biofilm P. aeruginosa PAO1 cells. In vivo, YXL-13 significantly prolonged the lifespan of wildtype Caenorhabditis elegans N2 infected by P. aeruginosa PAO1. In conclusion, YXL-13 is a candidate agent for antibiotic-resistant P. aeruginosa PAO1and provides a method for finding new antibacterial drugs.
