tert-butyl 4-{5-[(5R)-5-hydroxymethyl-2-oxo-1,3-oxazolan-3-yl]pyridin-2-yl}piperazine-1-carboxylate | 510729-43-8

• 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: tert-butyl 4-{5-[(5R)-5-hydroxymethyl-2-oxo-1,3-oxazolan-3-yl]pyridin-2-yl}piperazine-1-carboxylate
• 英文别名: (R)-N-3-[2-[4-(N-t-butoxycarbonyl)piperazin-1-yl]pyridin-5-yl]-2-oxooxazolidin-5-ylmethanol；(S)-N-3-[2-[4-(N-t-butoxycarbonyl)piperazin-1-yl]pyridin-5-yl]-2-oxooxazolidin-5-ylmethanol；tert-butyl 4-[5-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]pyridin-2-yl]piperazine-1-carboxylate
• CAS: 510729-43-8
• 化学式: C₁₈H₂₆N₄O₅
• 分子量: 378.428
• InChiKey: QEHIBMGBBMODNM-CQSZACIVSA-N

物化性质

• 沸点：
  567.1±50.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-{5-[(5R)-5-hydroxymethyl-2-oxo-1,3-oxazolan-3-yl]pyridin-2-yl}piperazine-1-carboxylate 在 palladium on activated charcoal 三乙基硅烷 、 sodium azide 、 氢气 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 N-[(5S)-2-oxo-3-(6-piperazin-1-yl-pyridin-3-yl)-oxazolidin-5-ylmethyl]-acetamide
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Oxazolidinone–Quinolone Hybrids

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(03)00083-x
• 作为产物：
  描述：

  4-(5-氨基吡啶-2-基)哌嗪-1-羧酸叔丁酯 在 正丁基锂 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 0.17h， 生成 tert-butyl 4-{5-[(5R)-5-hydroxymethyl-2-oxo-1,3-oxazolan-3-yl]pyridin-2-yl}piperazine-1-carboxylate
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Oxazolidinone–Quinolone Hybrids

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(03)00083-x

文献信息

• [EN] OXAZOLIDINONE DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES DE L'OXAZOLIDINONE, AGENTS ANTIBACTERIENS
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2004009587A1

  公开（公告）日：2004-01-29

  The present invention provides novel compounds of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly provides novel oxazolidinone derivatives of the general formula (I).

  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、溶剂合物、药用可接受盐和含有它们的药用可接受组合物。本发明特别提供了一般式(I)的新噁唑啉酮衍生物。
• [EN] OXAZOLE DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSES NOUVEAUX UTILES COMME AGENTS ANTI-BACTERIENS
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2005003087A3

  公开（公告）日：2005-03-17
• WO2008/29266
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.