butyl (5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: butyl (5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide
• 英文别名: butyl (5R)-3-[4-(1,1-dioxothian-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxylate
• 化学式: C₁₉H₂₃F₂NO₆S
• 分子量: 431.458
• InChiKey: PXKCAHQVBWTWGM-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  butyl (5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以79%的产率得到(5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide
  参考文献：
  名称：

  Antibacterial Oxazolidinones Possessing a Novel C-5 Side Chain. (5R)-trans-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic Acid Amide (PF-00422602), a New Lead Compound

  摘要：

  Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.

  DOI：

  10.1021/jm070708p
• 作为产物：
  描述：

  (-)-butyl (5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 18.0h， 以95%的产率得到butyl (5R)-3-[3,5-difluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide
  参考文献：
  名称：

  Antibacterial Oxazolidinones Possessing a Novel C-5 Side Chain. (5R)-trans-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic Acid Amide (PF-00422602), a New Lead Compound

  摘要：

  Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.

  DOI：

  10.1021/jm070708p

文献信息

• Antibacterial Oxazolidinones Possessing a Novel C-5 Side Chain. (5<i>R</i>)-<i>trans</i>-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic Acid Amide (PF-00422602), a New Lead Compound
  作者：Toni-Jo Poel、Richard C. Thomas、Wade J. Adams、Paul A. Aristoff、Michael R. Barbachyn、Frederick E. Boyer、Joan Brieland、Roger Brideau、Joanne Brodfuehrer、Alan P. Brown、Allison L. Choy、Michael Dermyer、Michael Dority、Charles W. Ford、Robert C. Gadwood、Debra Hanna、Cai Hongliang、Michael D. Huband、Christopher Huber、Rose Kelly、Ji-Young Kim、Joseph P. Martin、Paul J. Pagano、Daniel Ross、Laura Skerlos、Mark C. Sulavik、Tong Zhu、Gary E. Zurenko、J. V. N. Vara Prasad

  DOI：10.1021/jm070708p

  日期：2007.11.1

  Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.