1-[2-(3-Hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carboxylic acid | 442151-52-2

• 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: 1-[2-(3-Hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carboxylic acid
• CAS: 442151-52-2
• 化学式: C₂₆H₂₁NO₆
• 分子量: 443.456
• InChiKey: PHRIVUUDEGXOQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-(3-Hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carboxylic acid 在 copper(ll) sulfate pentahydrate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-[[3-[[1-[3-[[1-[2-(3-Hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carbonyl]amino]propyl]triazole-4-carbonyl]amino]-2-sulfopropanoyl]amino]acetic acid
  参考文献：
  名称：

  New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

  摘要：

  本文介绍了将疏水性荧光染料高效化学转化为可生物接合的水溶性衍生物的新合成方法。这些新型磺化后合成方法的基石是结合使用一种原始的磺化末端炔烃和一种金属介导的反应，即铜催化的惠斯根 1,3-二极环加成反应（"click "反应）或 Sonogashira 交叉偶联反应。

  DOI：

  10.1039/c2ob25428j
• 作为产物：
  描述：

  fluorescein free acid 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-[2-(3-Hydroxy-6-oxoxanthen-9-yl)benzoyl]piperidine-4-carboxylic acid
  参考文献：
  名称：

  New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions

  摘要：

  本文介绍了将疏水性荧光染料高效化学转化为可生物接合的水溶性衍生物的新合成方法。这些新型磺化后合成方法的基石是结合使用一种原始的磺化末端炔烃和一种金属介导的反应，即铜催化的惠斯根 1,3-二极环加成反应（"click "反应）或 Sonogashira 交叉偶联反应。

  DOI：

  10.1039/c2ob25428j

文献信息

• Water solubilization of xanthene dyes by post-synthetic sulfonation in organic media
  作者：Anthony Romieu、Delphine Tavernier-Lohr、Stéphane Pellet-Rostaing、Marc Lemaire、Pierre-Yves Renard

  DOI：10.1016/j.tetlet.2010.04.080

  日期：2010.6

  Highly water-soluble fluorescent fluorescein and rhodamine dyes were synthesized through amidification of their carboxylic acid functionality with original di- or tri-sulfonated amino linkers derived from taurine or α-sulfo-β-alanine. This post-synthetic derivatization was performed in organic media both to minimize the premature hydrolysis and to suppress the precipitation of the involved active ester

  通过用衍生自牛磺酸或α-磺基-β-丙氨酸的原始二或三磺化氨基接头酰胺化羧酸官能团，合成了高度水溶性的荧光素和若丹明染料。这种合成后的衍生反应是在有机介质中进行的，以最大程度地减少过早水解并抑制所涉及的荧光团活性酯的沉淀，这在标准Schotten-Baumann条件下经常会遇到。
• Membrane-Anchoring Fluorescent Probe
  申请人：Nagano Tetsuo

  公开号：US20080281104A1

  公开（公告）日：2008-11-13

  A membrane anchoring-type fluorescent probe consisting of a compound comprising a phospholipid residue, a fluorescent probe compound residue, and a linker which binds the residues (e.g., the compound represented by the following formula).

  一种膜锚定型荧光探针，由包含磷脂残基、荧光探针化合物残基和连接剂的化合物组成（例如，由以下公式表示的化合物）。
• Xanthene derivatives
  申请人：——

  公开号：US20040054195A1

  公开（公告）日：2004-03-18

  Secondary amide xanthene derivatives, termed “xanthamides”, and other xanthene derivatives, are obtained in one form as fluorescent dyes which can have much higher photostability than related dyes such as fluorescein and BODIPY-FL. Examples are presented in which the synthesis begins with 5-carboxyfluorescein, an inexpensive reagent. Related carboxyxanthenes employed in other dyes such as rhodamines can also be used as starting materials. Simple synthetic steps yield compounds which exemplify this invention. Other notable properties of the xanthamide dyes include the option of pH-independent fluorescence, and the ease of controlling their functional and other groups. This means that a diversity of xanthamide and related xanthene dyes can be prepared with a broad variation of physicochemical properties to enhance the usefulness of fluorescence in biological and chemical analysis, and in other areas. In a second form xanthamides are formed which can be used as precursors of xanthamide dyes, especially as indicators or quenchers of reactive oxygen or free radical species.

  二级酰胺黄素衍生物，称为“黄酰胺”，以及其他黄素衍生物，以一种形式获得，作为荧光染料，其光稳定性可以比相关染料如荧光素和BODIPY-FL高得多。其中一些示例是以5-羧基荧光素开始合成的，这是一种廉价试剂。其他用于制备其他染料（如罗丹明）的相关羧基黄素也可以用作起始材料。简单的合成步骤产生了代表这种发明的化合物。黄酰胺染料的其他显着特性包括无pH依赖性荧光的选择，以及控制其功能和其他基团的易于性。这意味着可以准备各种具有广泛物理化学性质变化的黄酰胺和相关黄素染料，以增强在生物和化学分析以及其他领域中荧光的有用性。在第二种形式中，形成了可以用作黄酰胺染料的前体的黄酰胺，特别是作为反应性氧或自由基物种的指示剂或猝灭剂。
• Synthesis, Biological Evaluation, and <i>in Vivo</i> Imaging of the first Camptothecin–Fluorescein Conjugate
  作者：Arnaud Chevalier、Martine Dubois、Vadim Le Joncour、Sébastien Dautrey、Céline Lecointre、Anthony Romieu、Pierre-Yves Renard、Hélène Castel、Cyrille Sabot

  DOI：10.1021/bc3005304

  日期：2013.7.17

  The first synthesis and photophysical properties of a fluorecently labeled camptothecin derivative, namely, camptothecin-FI (CPT-FI), an antitumoral agent that targets topoisomerase I, are reported. The preparation of this fluorescent conjugate is based on a highly convergent and flexible approach which enables the rapid chemical modification of the AB ring system of this fragile pentacyclic alkaloid, aimed at introducing an anchoring point to graft the fluorophore. The selection of a fluorescein analogue as the reporter group has enabled us to get the first green-emitting CPT conjugate exhibiting valuable spectral properties and retaining biological properties of native CPT. Indeed, in biological models, i.e., glioma cell lines U87 and/or T98, the kinetics of cell endocytosis, as well as the efficacy of CPT-FI were compared to those of CPT. CPT-FI fluorescence was measured in the cytosolic compartment of T98 glioma cells from 5 min treatment and remained detectable until 48 h. As CPT, CPT-FI drastically inhibited glioma growth and cell cycle but exhibited a reduced affinity as compared to the native CPT. In vivo and ex vivo imaging studies of CPT-FI intratumoraly injected into a model of NIH-3T3 marine tumor xenografts in nude mice, showed accumulation around the injected site area, which is very promising to target tumors and follow biodistribution in vivo.
• New insights into the water-solubilisation of fluorophores by post-synthetic “click” and Sonogashira reactions
  作者：Cédrik Massif、Sébastien Dautrey、Alexandre Haefele、Raymond Ziessel、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1039/c2ob25428j

  日期：——

  New synthetic methodologies for the efficient chemical conversion of hydrophobic fluorescent dyes into bioconjugable and water-soluble derivatives are described. The combined use of an original sulfonated terminal alkyne and a metal-mediated reaction, namely the copper-catalysed Huisgen 1,3-dipolar cycloaddition (“click” reaction) or the Sonogashira cross-coupling, is the cornerstone of these novel post-synthetic sulfonation approaches.

  本文介绍了将疏水性荧光染料高效化学转化为可生物接合的水溶性衍生物的新合成方法。这些新型磺化后合成方法的基石是结合使用一种原始的磺化末端炔烃和一种金属介导的反应，即铜催化的惠斯根 1,3-二极环加成反应（"click "反应）或 Sonogashira 交叉偶联反应。