O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methylthiocarbamate | 1443005-57-9

• 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-fluorophenyl)-2-oxooxazolidin-5-yl)methylthiocarbamate
• 英文别名: tert-butyl 5-[2-fluoro-4-[(5S)-5-[(methoxycarbothioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2-(2,2,2-trifluoroacetyl)-1,2,5-triazepane-1-carboxylate
• CAS: 1443005-57-9
• 化学式: C₂₃H₂₉F₄N₅O₆S
• 分子量: 579.573
• InChiKey: VCVMDMZHGKYQJG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  12

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-fluorophenyl)-2-oxooxazolidin-5-yl)methylthiocarbamate 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)-3-{3-fluoro-4-[1-(hydroxyacetyl)[1,2,5]-triazepan-5-yl]phenyl}-2-oxo-5-oxazolidinyl]methyl}O-methoxycarbamate
  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：

  [1,2,5]triazepane-1-carboxylic acid tert-butyl ester 在 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 sodium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氯乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 81.84h， 生成 O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)-2-(2,2,2-trichloroacetyl)[1,2,5]triazepan-5-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)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

文献信息

• Antibacterial oxazolidinone analogues having a N-hydroxyacetyl-substituted seven-membered [1,2,5]triazepane or [1,2,5]oxadiazepane C-ring unit
  作者：Hideyuki Suzuki、Iwao Utsunomiya、Koichi Shudo、Norio Fukuhara、Tsutomu Iwaki、Tatsuro Yasukata

  DOI：10.1016/j.ejmech.2013.03.003

  日期：2013.5

  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.