5(R)-(isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(2-(tert-butoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one | 1443005-68-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5(R)-(isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(2-(tert-butoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one
• CAS: 1443005-68-2
• 化学式: C₂₇H₃₅F₂N₅O₈
• 分子量: 595.6
• InChiKey: DZIWYOOTVFPLAN-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  42.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127.12
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5(R)-(isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(2-(tert-butoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以73%的产率得到5(S)-(isoxazol-3-yl-aminomethyl)-3-(3,5-difluoro-4-([1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one
  参考文献：
  名称：

  Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit

  摘要：

  We synthesized a series of oxazolidinone analogues bearing a N-hydroxyacetyl-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit as homologues of an earlier drug candidate, eperezolid. Several of these compounds exhibited potent in vitro antibacterial activities towards not only Gram-positive, but also Gram-negative and linezolid-resistant pathogens. Compounds 21a and 21b, bearing a thiocarbamate side chain, showed high in vivo activity against methicillin-resistant Staphylococcus aureus SR3637, together with a promising safety profile in terms of weak inhibition of monoamine oxidase and cytochrome P450 isozymes. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.003
• 作为产物：
  描述：

  3,4,5-三氟硝基苯 在 正丁基锂 、 三丁基膦 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 62.84h， 生成 5(R)-(isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(2-(tert-butoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one
  参考文献：
  名称：

  Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit

  摘要：

  We synthesized a series of oxazolidinone analogues bearing a N-hydroxyacetyl-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit as homologues of an earlier drug candidate, eperezolid. Several of these compounds exhibited potent in vitro antibacterial activities towards not only Gram-positive, but also Gram-negative and linezolid-resistant pathogens. Compounds 21a and 21b, bearing a thiocarbamate side chain, showed high in vivo activity against methicillin-resistant Staphylococcus aureus SR3637, together with a promising safety profile in terms of weak inhibition of monoamine oxidase and cytochrome P450 isozymes. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.003