(5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one | 252279-84-8

• 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: (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one
• 英文别名: (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-(1,2-oxazol-3-yloxymethyl)-1,3-oxazolidin-2-one
• CAS: 252279-84-8
• 化学式: C₁₇H₁₉FN₄O₄
• 分子量: 362.361
• InChiKey: KZXIBRLRTUPSCT-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one 在 盐酸羟胺 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-{2-fluoro-4-[5-(isoxazol-3-yloxymethyl)-2-oxo-oxazolidin-3-yl]-phenyl}-piperazin-1-yl)-N-hydroxy-acetamidine
  参考文献：
  名称：

  带有N-羟基乙am取代基的新型恶唑烷酮的合成及其抗菌活性。

  摘要：

  合成了具有N-羟基乙moiety部分的新型恶唑烷酮抗菌剂，其在C-5末端具有多样性。已针对一组临床相关的革兰氏阳性和革兰氏阴性病原体对这些化合物进行了评估。该系列中的大多数类似物显示出优于利奈唑胺的活性，并且本文还公开了选定的恶唑烷酮的体内功效。

  DOI：

  10.1016/j.bmcl.2006.01.109
• 作为产物：
  描述：

  (R)-4-(2-氟-4-(5-(羟基甲基)-2-氧代噁唑啉-3-基)苯基)哌嗪-1-羧酸叔丁酯 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  带有N-羟基乙am取代基的新型恶唑烷酮的合成及其抗菌活性。

  摘要：

  合成了具有N-羟基乙moiety部分的新型恶唑烷酮抗菌剂，其在C-5末端具有多样性。已针对一组临床相关的革兰氏阳性和革兰氏阴性病原体对这些化合物进行了评估。该系列中的大多数类似物显示出优于利奈唑胺的活性，并且本文还公开了选定的恶唑烷酮的体内功效。

  DOI：

  10.1016/j.bmcl.2006.01.109

文献信息

• Synthesis and antibacterial activity of novel oxazolidinones with methylene oxygen- and methylene sulfur-linked substituents at C5-position
  作者：Sonali Rudra、Fnu Sangita、Arti Gujrati、Manisha Pandya、Pragya Bhateja、Tarun Mathur、Smita Singhal、Ashok Rattan、Mohammed Salman、Biswajit Das

  DOI：10.1016/j.bmcl.2007.06.056

  日期：2007.9

  Novel oxazolidinone derivatives of the lead compound RBx 8700, containing methylene oxygen- and methylene sulfur-linked substituents at the C5-position, were synthesized. Antibacterial screening of these compounds against a panel of resistant and susceptible Gram-positive and fastidious Gram-negative bacteria gave compounds 2 and 4 as new antibacterial agents.

  合成了铅化合物RBx 8700的新型恶唑烷酮衍生物，该衍生物在C5位上包含亚甲基氧连接和亚甲基硫连接的取代基。针对一组抗药性和易感性革兰氏阳性菌和革兰氏阴性菌对这些化合物进行抗菌筛选，得到化合物2和4作为新的抗菌剂。
• [EN] OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS<br/>[FR] DERIVES D'OXAZOLIDINONE A ACTIVITE ANTIMICROBIENNE
  申请人：RANBAXY LAB LTD

  公开号：WO2006035283A1

  公开（公告）日：2006-04-06

  The present invention relates to substituted phenyl oxazolidinones and processes for preparing thereof. This invention also relates to pharmaceutical compositions comprising compounds of the present invention. Such compounds can be useful antimicrobial agents that can be particularly effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria (e.g., multiple-resistant staphylococci, streptococci and enterococci), anaerobic organisms (e.g., Bacterioides spp. and Clostridia spp. species), and acid-fast organisms (e.g., Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp).Formula (I).

  本发明涉及取代苯基噁唑烷酮及其制备方法。本发明还涉及包含本发明化合物的药物组合物。这些化合物可以是有用的抗微生物剂，特别是对许多人类和兽医病原体具有特效，包括革兰氏阳性厌氧细菌（例如，多耐药葡萄球菌、链球菌和肠球菌）、厌氧菌（例如，拟杆菌属和梭菌属物种）和耐酸菌（例如，结核分枝杆菌、分枝杆菌和分枝杆菌属）。公式（I）。
• Synthesis and biological activity of novel oxazolidinones
  作者：Biswajit Das、A.V.S. Rajarao、Sonali Rudra、Ajay Yadav、Abhijit Ray、Manisha Pandya、Ashok Rattan、Anita Mehta

  DOI：10.1016/j.bmcl.2009.09.054

  日期：2009.11

  A number of 5-substituted derivatives of Ranbezolid, a novel oxazolidinone were synthesized. Antibacterial activity of the compounds against a number of sensitive and resistant bacteria showed promising results. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.