2-(6-Methoxy-3-oxo-3H-xanthen-9-yl)-5-[(piperazine-1-carbothioyl)-amino]-benzoic acid methyl ester | 205327-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(6-Methoxy-3-oxo-3H-xanthen-9-yl)-5-[(piperazine-1-carbothioyl)-amino]-benzoic acid methyl ester
• 英文别名: Methyl 2-(3-methoxy-6-oxoxanthen-9-yl)-5-(piperazine-1-carbothioylamino)benzoate
• CAS: 205327-31-7
• 化学式: C₂₇H₂₅N₃O₅S
• 分子量: 503.579
• InChiKey: ZTQIWTIMRSVFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(6-Methoxy-3-oxo-3H-xanthen-9-yl)-5-[(piperazine-1-carbothioyl)-amino]-benzoic acid methyl ester 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl 5-[[4-[3-[3-[3-[[2-[hydroxy(methyl)amino]-2-oxoethyl]amino]-3-oxopropoxy]-2,2-bis[[3-[[2-[hydroxy(methyl)amino]-2-oxoethyl]amino]-3-oxopropoxy]methyl]propoxy]propanoyl]piperazine-1-carbothioyl]amino]-2-(3-methoxy-6-oxoxanthen-9-yl)benzoate
  参考文献：
  名称：

  Modular Fluorescent-Labeled Siderophore Analogues

  摘要：

  Biomimetic analogues 1 of the microbial siderophore (iron carrier) ferrichrome were labeled via piperazine with various fluorescent markers at a site not interfering with iron binding or receptor recognition (compounds 10-12). These iron carriers were built from a tetrahedral carbon symmetrically extended with three strands, each containing an amino acid (G = glycyl, A = alanyl, L = leucyl and P = phenylalanyl) and terminated by a hydroxamic acid, which together define an octahedral iron-binding domain. A fourth exogenous strand provided the site for connecting various fluorescent markers via a short bifunctional linker. Iron(III) titrations, along with fluorescence spectroscopy, generated quenching of fluorescence emission of some of the probes used. The quenching process fits the Perrin model which reinforces the intramolecular quenching process, postulated previously.(1) All tested compounds, regardless of their probe size, polarity, or the linker binding them to the siderophore analogue, promote growth of Pseudomonas putida with the same efficacy as the nonlabeled analogues 1, with the added benefit of signaling microbial activity by fluorescence emission. All G derivatives of compounds 10-12 were found to parallel the behavior of natural ferrichrome, whereas A derivatives mediated only a modest iron(III) uptake by P. putida. Incubation of various Pseudomonas strains with iron(III)-loaded G derivatives resulted in the build-up of the labels' fluorescence in the culture medium to a much larger extent than from the corresponding A derivatives. The fluorescence buildup corresponds to iron utilization by the cells and the release of the fluorescent labeled desferrisiderophore from the cell to the media. The fact that the microbial activity of these compounds is not altered by attachment of various fluorescent markers via a bifunctional linker proposes their application as diagnostic tools for detecting and identifying pathogenic microorganisms.

  DOI：

  10.1021/jm970581b
• 作为产物：
  描述：

  4-[3-Methoxycarbonyl-4-(6-methoxy-3-oxo-3H-xanthen-9-yl)-phenylthiocarbamoyl]-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-(6-Methoxy-3-oxo-3H-xanthen-9-yl)-5-[(piperazine-1-carbothioyl)-amino]-benzoic acid methyl ester
  参考文献：
  名称：

  Modular Fluorescent-Labeled Siderophore Analogues

  摘要：

  Biomimetic analogues 1 of the microbial siderophore (iron carrier) ferrichrome were labeled via piperazine with various fluorescent markers at a site not interfering with iron binding or receptor recognition (compounds 10-12). These iron carriers were built from a tetrahedral carbon symmetrically extended with three strands, each containing an amino acid (G = glycyl, A = alanyl, L = leucyl and P = phenylalanyl) and terminated by a hydroxamic acid, which together define an octahedral iron-binding domain. A fourth exogenous strand provided the site for connecting various fluorescent markers via a short bifunctional linker. Iron(III) titrations, along with fluorescence spectroscopy, generated quenching of fluorescence emission of some of the probes used. The quenching process fits the Perrin model which reinforces the intramolecular quenching process, postulated previously.(1) All tested compounds, regardless of their probe size, polarity, or the linker binding them to the siderophore analogue, promote growth of Pseudomonas putida with the same efficacy as the nonlabeled analogues 1, with the added benefit of signaling microbial activity by fluorescence emission. All G derivatives of compounds 10-12 were found to parallel the behavior of natural ferrichrome, whereas A derivatives mediated only a modest iron(III) uptake by P. putida. Incubation of various Pseudomonas strains with iron(III)-loaded G derivatives resulted in the build-up of the labels' fluorescence in the culture medium to a much larger extent than from the corresponding A derivatives. The fluorescence buildup corresponds to iron utilization by the cells and the release of the fluorescent labeled desferrisiderophore from the cell to the media. The fact that the microbial activity of these compounds is not altered by attachment of various fluorescent markers via a bifunctional linker proposes their application as diagnostic tools for detecting and identifying pathogenic microorganisms.

  DOI：

  10.1021/jm970581b