5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester | 952151-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 5-[2,6-difluoro-4-(phenylmethoxycarbonylamino)phenyl]-1,2,5-oxadiazepane-2-carboxylate；tert-butyl 5-[2,6-difluoro-4-(phenylmethoxycarbonylamino)phenyl]-1,2,5-oxadiazepane-2-carboxylate
• CAS: 952151-42-7
• 化学式: C₂₃H₂₇F₂N₃O₅
• 分子量: 463.481
• InChiKey: SRGGIRZIEDDDJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester 在 吡啶 、 正丁基锂 、 sodium azide 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.01h， 生成 5(S)-(acetylaminomethyl)-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：

  5-benzyl 2-tert-butyl 1,2,5-oxadiazepane-2,5-dicarboxylate 在 palladium 10% on activated carbon 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 38.0h， 生成 5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  EP2208729

  摘要：

  公开号：

文献信息

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

  公开号：EP2009012B1

  公开（公告）日：2014-06-25
• 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.
• EP2208729
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.