Methyl 2-[3-(diethylamino)-6-oxoxanthen-9-yl]benzoate | 1326231-91-7

• 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: Methyl 2-[3-(diethylamino)-6-oxoxanthen-9-yl]benzoate
• 英文别名: methyl 2-[3-(diethylamino)-6-oxoxanthen-9-yl]benzoate
• CAS: 1326231-91-7
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: PBYKRTDSZAFZKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[3-(diethylamino)-6-oxoxanthen-9-yl]benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以2.4 g的产率得到6-(diethylamino)-9-(2-(hydroxymethyl)phenyl)-9H-xanthen-3-ol
  参考文献：
  名称：

  ENZYME-SPECIFIC FLUORESCENT COMPOUND CAPABLE OF BEING RETAINED IN CELLS

  摘要：

  提供了一种酶特异性荧光化合物，能够在细胞内保留，并能在靶细胞中特异性地发出荧光，特别是在能够表达报告酶如β-半乳糖苷酶的细胞中，并能共价结合到细胞中的蛋白质中，表现出优异的保留在细胞中的特性。该荧光化合物包括由公式（I'）或其盐所表示的化合物。在公式（I'）中，A、X、Y和R1至R9如权利要求1所述。

  公开号：

  US20170073321A1
• 作为产物：
  描述：

  间苯二酚 在 磷酸 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 Methyl 2-[3-(diethylamino)-6-oxoxanthen-9-yl]benzoate
  参考文献：
  名称：

  β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold

  摘要：

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.

  DOI：

  10.1021/ja204781t

文献信息

• FLUORESCENT PROBES FOR DETECTION OF COPPER
  申请人：The Regents Of The University Of California

  公开号：US20140051863A1

  公开（公告）日：2014-02-20

  The invention provides fluorescent sensors for the selective detection of a metal such as copper. The sensors may be considered to be derivatives of cyanine, fluorescein, rhodamine, rhodol, Tokyo green, or BODIPY. The sensors find particular use in detecting copper in cells and living animals.

  本发明提供了用于选择性地检测如铜等金属的荧光传感器。这些传感器可以被认为是青色素、荧光素、罗丹明、罗多醇、东京绿或BODIPY的衍生物。这些传感器在检测细胞和活体动物中的铜方面特别有用。
• US8865914B2
  申请人：——

  公开号：US8865914B2

  公开（公告）日：2014-10-21
• US9981934B2
  申请人：——

  公开号：US9981934B2

  公开（公告）日：2018-05-29
• β-Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold
  作者：Mako Kamiya、Daisuke Asanuma、Erina Kuranaga、Asuka Takeishi、Masayo Sakabe、Masayuki Miura、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja204781t

  日期：2011.8.24

  We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for beta-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize beta-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.
• ENZYME-SPECIFIC FLUORESCENT COMPOUND CAPABLE OF BEING RETAINED IN CELLS
  申请人：The University of Tokyo

  公开号：US20170073321A1

  公开（公告）日：2017-03-16

  Provided is an enzyme-specific fluorescent compound capable of being retained in cells, which can emit fluorescence specifically in a target cell, particularly a cell capable of expressing a reporter enzyme such as β-galactosidase, and can covalently bind to a protein in the cell to exhibit an excellent property of being retained in the cell. The fluorescent compound comprises a compound represented by formula (I′) or a salt thereof. In formula (I′), A, X, Y and R1 to R9 are as described in claim 1.

  提供了一种酶特异性荧光化合物，能够在细胞内保留，并能在靶细胞中特异性地发出荧光，特别是在能够表达报告酶如β-半乳糖苷酶的细胞中，并能共价结合到细胞中的蛋白质中，表现出优异的保留在细胞中的特性。该荧光化合物包括由公式（I'）或其盐所表示的化合物。在公式（I'）中，A、X、Y和R1至R9如权利要求1所述。