- Design and synthesis of biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety as novel antibacterial agents against Gram-positive bacteria
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Novel biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety were designed, synthesized and evaluated for their antibacterial activity. The key compounds 7 and 9 were synthesized by the knoevenagel condensation of intermediate aldehyde 5 with rhodanine derivatives 6a?6b. The preliminary study showed that compounds 7, 9 and 10e exhibited potent antibacterial activity with MIC values of 0.125 μg/mL against S. aureus, MRSA, MSSA, LREF and VRE pathogens, using linezolid and radezolid as the positive controls. The most promising compound 10e exhibited potent antibacterial activity against tested clinical isolates of MRSA, MSSA, VRE and LREF with MIC values in the range of 0.125–0.5 μg/mL, and the potency of 10e against clinical isolates of LREF was 64-fold higher than that of linezolid. Moreover, compound 10e was non-cytotoxic with an IC50 value of 91.04 μM against HepG2 cell. Together, compound 10e might serve as a novel antibacterial agent for further investigation.
- Wu, Yachuang,Ding, Xiudong,Xu, Sicong,Yang, Yifeng,Zhang, Xue,Wang, Chu,Lei, Hong,Zhao, Yanfang
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p. 496 - 502
(2019/01/04)
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- Oxazolidinone compound containing combined aromatic hydrazine and its preparation method
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The invention relates to oxazolidinone compound containing combined aromatic hydrazine shown in general formula I, its optical isomer, pharmaceutical acceptable salt and/or solvent compound, and it preparation method, and the drug composition containing the compound, wherein the substituent groups R1, R2, R3, X and A rings have the meaning given in the specification. The invention further relatesto the compound, the substituent group, solvent compound or application of its prodrug using as antibacterial drug in treatment, and application of treating gram positive bacterial infection and mycobacterium tuberculosis infection especially.
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Paragraph 0110; 0111
(2018/04/03)
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- Synthesis and antibacterial activity evaluation of novel biaryloxazolidinone analogues containing a hydrazone moiety as promising antibacterial agents
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A series of linezolid analogues containing a hydrazone moiety were designed, synthesized and evaluated for their antibacterial activity. Most compounds exhibited more potent antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens as compared with linezolid and radezolid. Compounds 9a, 9c, 9f, 9g, 10m and 10t were more potent against tested clinical isolates of MRSA, MSSA, VRE and LREF as compared to linezolid. Compound 9a exhibited comparable activity with linezolid against human MAO-A for safety evaluation and showed moderate metabolism in human liver microsome. The most promising compound 9a showed remarkable antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens with MIC value of 0.0675 mg/mL, respectively, which was 15- to 30-fold more potent than linezolid.
- Wu, Yachuang,Ding, Xiudong,Ding, Liang,Zhang, Yongsheng,Cui, Lei,Sun, Lu,Li, Wei,Wang, Di,Zhao, Yanfang
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p. 247 - 258
(2018/09/18)
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- Heterocycle-containing biaryl oxazolidinone compound and preparation method thereof
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The invention relates to a heterocycle-containing biaryl oxazolidinone compound with the structural formula as shown in the figure I in the specification, or an optical isomer and a pharmaceutically acceptable salt and/or solvate thereof, a preparation method for the heterocycle-containing biaryl oxazolidinone compound as well as the optical isomer and the pharmaceutically acceptable salt and/or solvate thereof, and a pharmaceutical composition containing the compound. According to the heterocycle-containing biaryl oxazolidinone compound, the substituent groups R1, R2, R3, R4 and A-ring have the meanings given in the specification. The invention also relates to application of the compound as well as the pharmaceutically acceptable salt and solvate or a prodrug thereof as an antibacterial drug in treatment, especially in treatment of gram-positive bacterial infection and mycobacterium tuberculosis infection. (Please see the figure I in the specification for the structural formula of theheterocyclic ring-containing biaryl oxazolidinone compound.).
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Paragraph 0141-0144
(2019/01/08)
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- Preparation method of biaryl oxazolidone intermediate
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The invention relates to a preparation method of a biaryl oxazolidone intermediate (5S)-N-[[3-(3-fluoro-4-iodophenyl)-2-oxooxazolidine-5-ol]methyl]acetamine (I). According to the method, the intermediate is prepared with m-fluoroaniline as an initial raw material through amino protection, iodination and cyclization sequentially. Compared with a reported preparation method of the biaryl oxazolidone intermediate, the method adopts a short route, increases the yield, greatly reduces the cost and is more suitable for industrial production.
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Paragraph 0034-0036
(2017/07/11)
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- A PROCESS FOR THE PREPARATION OF TEDIZOLID PHOSPHATE
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The present invention provides a process for the preparation of tedizolid phosphate.
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Page/Page column 14
(2016/06/28)
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- Palladium-Catalyzed Carbamate-Directed Regioselective Halogenation: A Route to Halogenated Anilines
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This study describes an efficient method for ortho-selective halogenation of N-arylcarbamates under mild conditions for the first time. Although being weakly coordinating, N-arylcarbamates act very well as a removable directing group for activation of C-H bonds. The developed procedure results in extremely valuable halogenated N-arylcarbmates that can further be hydrolyzed to halogenated anilines. The obtained reaction conditions showed broad scope and wide functional group tolerance. All the products were formed in good yields with extremely high selectivity.
- Moghaddam, Firouz Matloubi,Tavakoli, Ghazal,Saeednia, Borna,Langer, Peter,Jafari, Behzad
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p. 3868 - 3876
(2016/05/24)
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- Aniline carbamates: A versatile and removable motif for palladium-catalyzed directed c-h activation
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The aniline carbamate is introduced as a new removable directing group for C-H activation. Its versatility and ability as a directing group are demonstrated by its use in the ortho-arylation of a wide variety of aniline derivatives under palladium(II) catalysis, with symmetric diaryliodonium salts as aryl donors. The reaction differs from previously reported arylations in its selectivity and its mechanism, as elucidated by kinetic and isotopic experiments. The directing group can also be easily removed under a variety of conditions.
- Uhlig, Nick,Li, Chao-Jun
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supporting information
p. 12066 - 12070
(2015/03/31)
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- A microfluidic flow chemistry platform for organic synthesis: the Hofmann rearrangement
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We report on the use of commercially available chemical microreactors to effect the Hofmann rearrangement of aromatic amides to the corresponding carbamates. Crown Copyright
- Palmieri, Alessandro,Ley, Steven V.,Hammond, Kelvin,Polyzos, Anastasios,Baxendale, Ian R.
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scheme or table
p. 3287 - 3289
(2009/08/07)
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- A new and convenient in-situ method of generating phenyl isocyanates from anilines using oxalyl chloride
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A new and convenient method of generating phenyl isocyanates from anilines using oxalyl chloride is described. Acylation of a variety of substituted aniline hydrochlorides with oxalyl chloride affords the intermediate oxamic chlorides, which smoothly undergo thermal decomposition to the corresponding isocyanates.
- Oh, Lynette M.,Spoors, P. Grant,Goodman, Richard M.
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p. 4769 - 4771
(2007/10/03)
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- Dihydroindole and tetrahydroquinoline derivatives
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The present invention relates to novel dihydroindole and tetrahydroquinoline derivatives and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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- Indole and dihydroindole derivatives
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The present invention relates to indole derivatives, dihydroindole derivatives and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.
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