{[(5S)-3-[3-fluoro-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl}-carbamothioic acid methyl ester | 268208-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: {[(5S)-3-[3-fluoro-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl}-carbamothioic acid methyl ester
• 英文别名: O-Methyl (S)-N-[3-[3-fluoro-4-(piperazin-1-yl)phenyl]-2-oxooxazolidin-5-yl]-methylthiocarbamate；(S)-O-methyl (3-(3-fluoro-4-(piperazin-1-yI)phenyl)-2-oxo-oxazolidin-5-yl)-methylcarbamothioate；(S)-O-methyl (3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylcarbamothioate；O-methyl N-[[(5S)-3-(3-fluoro-4-piperazin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamothioate
• CAS: 268208-73-7
• 化学式: C₁₆H₂₁FN₄O₃S
• 分子量: 368.432
• InChiKey: VYRRFWCVYZWMHM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {[(5S)-3-[3-fluoro-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl}-carbamothioic acid methyl ester 以 水 、 溶剂黄146 为溶剂， 生成 O-Methyl (S)-N-[3-[4-(4-carbamoylpiperazin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-yl]methylthiocarbamate
  参考文献：
  名称：

  EP1130016

  摘要：

  公开号：
• 作为产物：
  描述：

  O-methyl (S)-N-[3-[4-(4-tert-butoxycarbonylpiperazin-1-yl)-3-fluorophenyl]-2-oxooxazolidin-5-yl]methylthiocarbamate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.25h， 以99%的产率得到{[(5S)-3-[3-fluoro-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl}-carbamothioic acid methyl ester
  参考文献：
  名称：

  WO2009/1192

  摘要：

  公开号：

文献信息

• NOVEL COMPOUND AND THEIR USE
  申请人：Pushpan Simi

  公开号：US20100234390A1

  公开（公告）日：2010-09-16

  The present invention provides novel compounds of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts and compositions, metabolites and prodrugs thereof. The novel compounds are useful as antibacterial agents in the treatment of conditions such as nosocomial pneumonia, community acquired pneumonia, infections caused by vancomycin resistant enterococci (VRE), methicillin resistant Staphylococcus aureus (MRSA), Heamophilus influenzae (HI) and penicillin resistant Streptococcus pneumoniae (PRSP). The compounds of the present invention are effective against a number of human or animal pathogens including VRE, PRSP, HI and MRSA.

  本发明提供了一般式（I）的新化合物，它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、水合物、溶剂化物、药学上可接受的盐和组合物、代谢物和前药。这些新化合物可用作抗菌剂，用于治疗诸如医院获得性肺炎、社区获得性肺炎、由耐万古霉素肠球菌（VRE）、耐甲氧西林金黄色葡萄球菌（MRSA）、流感嗜血杆菌（HI）和耐青霉素的肺炎链球菌（PRSP）引起的感染等疾病。本发明的化合物对包括VRE、PRSP、HI和MRSA在内的许多人类或动物病原体都有效。
• Design, Synthesis and Biological Evaluation of Oxazolidinone–Quinolone Hybrids
  作者：Christian Hubschwerlen、Jean-Luc Specklin、Christine Sigwalt、Susanne Schroeder、Hans H Locher

  DOI：10.1016/s0968-0896(03)00083-x

  日期：2003.5

  Oxazolidinone-quinolone hybrids that combine the pharmacophores of a quinolone and an oxazolidinone were synthesised and shown to be active against a variety of resistant and susceptible Gram-positive and fastidious Gram-negative organisms. The best compounds in this series overcome all types of resistance in relevant clinical Gram-positive pathogens. The nature of the spacer greatly influences the antibacterial activity. The dual mode of action could be demonstrated for compounds having a piperazinyl spacer. Antibacterial activity was higher at acidic pH. (C) 2003 Elsevier Science Ltd. All rights reserved.
• WO2009/1192
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel and potent oxazolidinone antibacterials featuring 3-indolylglyoxamide substituents
  作者：Mohamed Takhi、Gurpreet Singh、C. Murugan、Nirvesh Thaplyyal、Soma Maitra、K.M. Bhaskarreddy、P.V.S. Amarnath、Arundhuti Mallik、T. Harisudan、Ravi Kumar Trivedi、K. Sreenivas、N. Selvakumar、Javed Iqbal

  DOI：10.1016/j.bmcl.2008.03.043

  日期：2008.9

  Novel oxazolidinone antibacterials bearing a variety of 3-indolylglyoxamide substituents have been explored in an effort to improve the spectrum and potency of this class of agents. A subclass of this series was also made with the diversity at C-5 terminus. These derivatives have been screened against a panel of clinically relevant Gram-positive pathogens and fastidious Gram-negative organisms. Several analogs in this series were identified with in vitro activity superior to linezolid ( MIC = 0.25-2 mu g/ mL). Compounds 10a, 10c, 10e and 10f displayed activity against linezolid resistant Gram-positive organisms (MIC = 2-4 mu g/ mL). Selected oxazolidinones were evaluated for in vivo efficacy against a mouse systemic infection model. (C) 2008 Elsevier Ltd. All rights reserved.
• EP1130016
  申请人：——

  公开号：——

  公开（公告）日：——