174649-06-0Relevant academic research and scientific papers
An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants
Phetsang, Wanida,Blaskovich, Mark A.T.,Butler, Mark S.,Huang, Johnny X.,Zuegg, Johannes,Mamidyala, Sreeman K.,Ramu, Soumya,Kavanagh, Angela M.,Cooper, Matthew A.
, p. 4490 - 4498 (2014/09/17)
An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy.
Discovery of a novel nitroimidazolyl-oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation
Khalaj, Ali,Nakhjiri, Maryam,Negahbani, Amir Soheil,Samadizadeh, Marjaneh,Firoozpour, Loghman,Rajabalian, Saeed,Samadi, Nasrin,Faramarzi, Mohammad Ali,Adibpour, Neda,Shafiee, Abbas,Foroumadi, Alireza
experimental part, p. 65 - 70 (2011/02/25)
A number of linezolid analogues containing a nitroaryl-1,3,4-thiadiazole moiety, were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analogue 1b exhibited more potent inhibitory activity, with respect to other synthesized compounds and reference drug linezolid. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that compound 1c exhibit potent antibacterial activity against Gram-positive bacteria at non-cytotoxic concentrations.
BORON CONTAINING SMALL MOLECULES
-
, (2011/04/24)
This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.
Anti-tubercular agents. Part 6: Synthesis and antimycobacterial activity of novel arylsulfonamido conjugated oxazolidinones
Kamal, Ahmed,Shetti, Rajesh V.C.R.N.C.,Azeeza, Shaik,Swapna,Khan, M. Naseer A.,Khan, Inshad Ali,Sharma, Sandeep,Abdullah, Sheikh Tasduq
experimental part, p. 893 - 900 (2011/04/19)
As a part of investigation of new anti-tubercular agents in this laboratory, herein we describe the synthesis of a new class of arylsulfonamido conjugated oxazolidinones. The in vitro activity of these conjugated (6a-f, 7a-d, 9a-c and 11a-c) molecules aga
Synthesis and antibacterial activities of eperezolid analogs with glycinyl substitutions
Wang, Xiao-Jun,Wu, Ning,Du, Guang-Jian,Zhao, Shuang-Qi,Yan, Ming,Gu, Lian-Quan
scheme or table, p. 377 - 385 (2009/10/23)
A series of eperezolid analogs with glycinyl substitutions were prepared and their antibacterial activities were studied against a panel of susceptible and resistant Gram-positive bacteria. The compounds with N-arylacyl or N-heteroarylacyl glycinyl struct
A convenient synthesis of oxazolidinone derivatives linezolid and eperezolid from (S)-glyceraldehyde acetonide
Guangyu, Xu,Yi, Zhou,Chunhao, Yang,Yuyuan, Xie
, p. 316 - 319 (2008/09/19)
A new convenient method for the synthesis of oxazolidinone antibacterials Linezolid and Eperezolid from readily available (S)-glyceraldehyde acetonide was developed. The key steps include reductive amination of arylamine and (S)-glyceraldehyde acetonide in the presence of NaBH4 and 4 A sieve, followed by hydrolysis and regioselective cyclization.
Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation
Narina, Srinivasarao V.,Sudalai, Arumugam
, p. 6799 - 6802 (2007/10/03)
An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using d-proline-catalyzed asymmetric α-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis.
A short synthesis of oxazolidinone derivatives linezolid and eperezolid: A new class of antibacterials
Lohray, Braj B.,Baskaran, Sundarababu,Rao, B. Srinivasa,Reddy, B. Yadi,Rao, I. Nageswara
, p. 4855 - 4856 (2007/10/03)
Oxazolidinone derivatives such as Linezolid and Eperazolid, which are a new class of antibacterials, have been synthesized from 1,2,5,6-dianhydro- 3,4-isopropylidine-D-mannitol in good yield.
Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.
Brickner, Steven J.,Hutchinson, Douglas K.,Barbachyn, Michael R.,Manninen, Peter R.,Ulanowicz, Debra A.,et al.
, p. 673 - 679 (2007/10/03)
Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones.
Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents
Schaus, Scott E.,Jacobsen, Eric N.
, p. 7937 - 7940 (2007/10/03)
The dynamic kinetic resolution of racemic epichlorohydrin has been achieved via enantioselective asymmetric ring opening with TMSN3 catalyzed by the (salen)Cr(III)N3 complex 1. The resulting 3-azido-1-chloro-2-trimethylsiloxypropane product was obtained in high enantiomeric purity and incorporated into the synthesis of U-100592, a representative from a class of highly-promising aryl oxazolidinone antibacterial agents.
