(S)-N-((3-(3,5-difluoro-4-(1-carbamoyl-[1,2,5]triazepan-5-yl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-O-methylthiocarbamate | 952152-13-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-((3-(3,5-difluoro-4-(1-carbamoyl-[1,2,5]triazepan-5-yl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-O-methylthiocarbamate
• 英文别名: O-methyl N-[[(5S)-3-[4-(1-carbamoyl-1,2,5-triazepan-5-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamothioate
• CAS: 952152-13-5
• 化学式: C₁₇H₂₂F₂N₆O₄S
• 分子量: 444.462
• InChiKey: FEKXCZBHUWJYBZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  O-methyl (S)-N-(3-(4-(1-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)-3,5-difluorophenyl)-2-oxooxazolidin-5-yl)methylthiocarbamate 在 盐酸 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 21.17h， 生成 (S)-N-((3-(3,5-difluoro-4-(1-carbamoyl-[1,2,5]triazepan-5-yl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-O-methylthiocarbamate
  参考文献：
  名称：

  Synthesis and in vitro/in vivo antibacterial activity of oxazolidinones having thiocarbamate at C-5 on the A-ring and an amide- or urea-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane as the C-ring

  摘要：

  Oxazolidinones bearing a seven-membered [1,2,51triazepane or [1,2,51oxadiazepane heterocycle substituted with an amide or urea functionality as the C-ring and having a [1,2,3]triazole, a thiocarbamate, an isoxazole-3-ylamino, or a thioacetamide C-5 side chain unit on the A-ring instead of the typical acetamide were synthesized and their in vitro antibacterial activities towards various pathogens were evaluated. Several derivatives exhibited potent in vitro antibacterial activity toward not only Grampositive, but also Gram-negative and linezolid-resistant pathogens. The in vivo therapeutic effects of amide 11a and ureas 16e, 17a were 2- to 3-fold greater than that of linezolid in a systemic mouse infection model treated by intravenous administration. Furthermore, compounds 11a and 17a showed lower monoamine oxidase (MAO)-inhibitory activity than our previously reported potent oxazolidinone antibacterials 3a and 3b. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.002

文献信息

• Novel Compound Having Heterocyclic Ring
  申请人：Suzuki Hideyuki

  公开号：US20090299059A1

  公开（公告）日：2009-12-03

  The invention provides a novel oxazolidinone derivative represented by the formula (I): wherein Ring A is optionally substituted or fused and represents (A-1) at least 7-membered monocyclic hetero ring containing at least three N atoms; (A-2) at least 6-membered monocyclic hetero ring containing at least two N atoms and at least one O atom; or (A-3) at least 7-membered monocyclic hetero ring containing at least two N atoms and at least one S atom; X 1 is a single bond, —O—, —S—, —NR 2 —, —CO—, —CS—, —CONR 3 —, —NR 4 CO—, —SO 2 NR 5 —, and —NR 6 SO 2 — (wherein R 2 -R 6 are independently hydrogen or lower alkyl), or lower alkylene or lower alkenylene in which one of the preceding groups may intervene; Ring B is optionally substituted carbocycle or optionally substituted heterocycle; R 1 is hydrogen, or an organic residue which is able to bind to the 5-position of oxazolidinone ring in oxazolidinone antimicrobial agent, and an antibacterial agent containing the same.
• NOVEL COMPOUND HAVING HETEROCYCLIC RING
  申请人：SUZUKI Hideyuki

  公开号：US20120208997A1

  公开（公告）日：2012-08-16

  The invention provides a novel oxazolidinone derivative represented by the formula (I): wherein Ring A, X 1 , Ring B and R 1 are as described in the description, and an antibacterial agent containing the same.
• US8148362B2
  申请人：——

  公开号：US8148362B2

  公开（公告）日：2012-04-03
• Synthesis and in vitro/in vivo antibacterial activity of oxazolidinones having thiocarbamate at C-5 on the A-ring and an amide- or urea-substituted [1,2,5]triazepane or [1,2,5]oxadiazepane as the C-ring
  作者：Hideyuki Suzuki、Iwao Utsunomiya、Koichi Shudo、Norio Fukuhara、Tsutomu Iwaki、Tatsuro Yasukata

  DOI：10.1016/j.ejmech.2013.08.002

  日期：2013.11

  Oxazolidinones bearing a seven-membered [1,2,51triazepane or [1,2,51oxadiazepane heterocycle substituted with an amide or urea functionality as the C-ring and having a [1,2,3]triazole, a thiocarbamate, an isoxazole-3-ylamino, or a thioacetamide C-5 side chain unit on the A-ring instead of the typical acetamide were synthesized and their in vitro antibacterial activities towards various pathogens were evaluated. Several derivatives exhibited potent in vitro antibacterial activity toward not only Grampositive, but also Gram-negative and linezolid-resistant pathogens. The in vivo therapeutic effects of amide 11a and ureas 16e, 17a were 2- to 3-fold greater than that of linezolid in a systemic mouse infection model treated by intravenous administration. Furthermore, compounds 11a and 17a showed lower monoamine oxidase (MAO)-inhibitory activity than our previously reported potent oxazolidinone antibacterials 3a and 3b. (C) 2013 Elsevier Masson SAS. All rights reserved.