{[(S)-3-{3-fluoro-4-[1-(hydroxyacetyl)[1,2,5]-triazepan-5-yl]phenyl}-2-oxo-5-oxazolidinyl]methyl}O-methoxycarbamate | 952151-58-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: {[(S)-3-{3-fluoro-4-[1-(hydroxyacetyl)[1,2,5]-triazepan-5-yl]phenyl}-2-oxo-5-oxazolidinyl]methyl}O-methoxycarbamate
• 英文别名: O-methyl N-[[(5S)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)-1,2,5-triazepan-5-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamothioate
• CAS: 952151-58-5
• 化学式: C₁₈H₂₄FN₅O₅S
• 分子量: 441.483
• InChiKey: CVDJQEZVCYECCM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139
• 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)-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

文献信息

• NOVEL COMPOUND HAVING HETEROCYCLIC RING
  申请人：Research Foundation Itsuu Laboratory

  公开号：EP2009012A1

  公开（公告）日：2008-12-31

  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; X1 is a single bond, -O-, -S-, -NR2-, -CO-, -CS-, - CONR3-, -NR4CO-, -SO2NR5-, and -NR6SO2- (wherein R2 - R6 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; R1 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.

  本发明提供了一种由式 (I) 表示的新型噁唑烷酮衍生物： 其中 环 A 被任选取代或融合，并代表 (A-1) 至少含有三个 N 原子的 7 元单环杂环； (A-2) 至少含有两个 N 原子和至少一个 O 原子的 6 元单环杂环；或 (A-3) 至少含有两个 N 原子和至少一个 S 原子的 7 元单环杂环； X1为单键、-O-、-S-、-NR2-、-CO-、-CS-、-CONR3-、-NR4CO-、-SO2NR5-和-NR6SO2-（其中 R2 - R6 独立地为氢或低级烷基），或低级亚烷基或低级亚烯基，其中可介入前述基团之一； 环 B 是任选取代的碳环或任选取代的杂环； R1 是氢，或能够与恶唑烷酮类抗菌剂中恶唑烷酮环 5 位结合的有机残基、 以及含有相同成分的抗菌剂。
• 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.
• US8148362B2
  申请人：——

  公开号：US8148362B2

  公开（公告）日：2012-04-03
• 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.