O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3,5-difluorophenyl)-2-oxooxazolidin-5-yl)ethylthiocarbamate | 1443005-58-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3,5-difluorophenyl)-2-oxooxazolidin-5-yl)ethylthiocarbamate
• CAS: 1443005-58-0
• 化学式: C₂₃H₂₈F₅N₅O₆S
• 分子量: 597.563
• InChiKey: QUJMCANWVJPQPR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103.89
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3,5-difluorophenyl)-2-oxooxazolidin-5-yl)ethylthiocarbamate 在 吡啶 、 lithium hydroxide monohydrate 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.34h， 生成 (S)-N-((3-(3,5-difluoro-4-(1-(hydroxyacetyl)[1,2,5]triazepan-5-yl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-O-methylthiocarbamate
  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：

  5(S)-(aminomethyl)-3-(3,5-difluoro-4-(1-(tertbutoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.17h， 生成 O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3,5-difluorophenyl)-2-oxooxazolidin-5-yl)ethylthiocarbamate
  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