4-[4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazin-1-yl]-4-oxobutyric acid | 849114-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-[4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazin-1-yl]-4-oxobutyric acid
• 英文别名: 4-[4-(7-nitro-2,1,3-benzoxadiazol-4-yl)piperazino]-4-oxobutanoic acid；4-[4-(4-Nitro-2,1,3-benzoxadiazol-7-yl)piperazin-1-yl]-4-oxobutanoic acid；4-[4-(4-nitro-2,1,3-benzoxadiazol-7-yl)piperazin-1-yl]-4-oxobutanoic acid
• CAS: 849114-70-1
• 化学式: C₁₄H₁₅N₅O₆
• 分子量: 349.303
• InChiKey: YVLKLLJQVFBMCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazin-1-yl]-4-oxobutyric acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成
  参考文献：
  名称：

  A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe

  摘要：

  A fluorescent labelled artificial siderophore 1 was synthesized by coupling a 7-nitrobenz-2-oxa-1,3-diazole (NBD) derivative to the terminal amino group of a new trihydroxamate-containing amine 2, a ferrichrome-type siderophore that was obtained from tris(hydroxymethyl) amino methane. Compound I was shown to be a suitable tool for experiments on siderophore transport and uptake processes in various organisms cells and particularly in Candida albicans cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.053
• 作为产物：
  描述：

  4-硝基-7-哌嗪苯并氧杂噁二唑 在 sodium sulfate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-[4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazin-1-yl]-4-oxobutyric acid
  参考文献：
  名称：

  Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold

  摘要：

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.

  DOI：

  10.1021/ol1028173

文献信息

• Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold
  作者：Sabrina Noël、Laurent Guillon、Isabelle J. Schalk、Gaëtan L. A. Mislin

  DOI：10.1021/ol1028173

  日期：2011.3.4

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.
• A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe
  作者：H. Ouchetto、M. Dias、R. Mornet、E. Lesuisse、J.-M. Camadro

  DOI：10.1016/j.bmc.2004.11.053

  日期：2005.3.1

  A fluorescent labelled artificial siderophore 1 was synthesized by coupling a 7-nitrobenz-2-oxa-1,3-diazole (NBD) derivative to the terminal amino group of a new trihydroxamate-containing amine 2, a ferrichrome-type siderophore that was obtained from tris(hydroxymethyl) amino methane. Compound I was shown to be a suitable tool for experiments on siderophore transport and uptake processes in various organisms cells and particularly in Candida albicans cells. (C) 2004 Elsevier Ltd. All rights reserved.