9H-fluoren-9-ylmethyl N-(6'-aminospiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl)carbamate | 1416967-75-3

• 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: 9H-fluoren-9-ylmethyl N-(6'-aminospiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl)carbamate
• CAS: 1416967-75-3
• 化学式: C₃₅H₂₆N₂O₄
• 分子量: 538.602
• InChiKey: WEKWYGNOJYUIGU-UHFFFAOYSA-N

物化性质

• 沸点：
  704.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-(6'-aminospiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl)carbamate 在 吡啶 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Rational Design of Highly Sensitive Fluorescence Probes for Protease and Glycosidase Based on Precisely Controlled Spirocyclization

  摘要：

  We have synthesized and evaluated a series of hydroxymethyl rhodamine derivatives and found an intriguing difference of intramolecular spirocyclization behavior: the acetylated derivative of hydroxymethyl rhodamine green (Ac-HMRG) exists as a dosed spirocyclic structure in aqueous solution at physiological pH, whereas HMRG itself takes an open nonspirocyclic structure. Ac-HMRG is colorless and nonfluorescent, whereas HMRG is strongly fluorescent. On the basis of these findings, we have developed a general design strategy to obtain highly sensitive fluorescence probes for proteases and glycosidases, by replacing the acetyl group of Ac-HMRG with a substrate moiety of the target enzyme. Specific cleavage of the substrate moiety in the nonfluorescent probe by the target enzyme generates a strong fluorescence signal. To confirm the validity and flexibility of our strategy, we designed and synthesized fluorescence probes for leucine aminopeptidase (Leu-HMRG), fibroblast activation protein (Ac-GlyPro-HMRG), and beta-galactosidase (beta Gal-HMRG). All of these probes were almost nonfluorescent due to the formation of spirocyclic structure, but were converted efficiently to highly fluorescent HMRG by the target enzymes. We confirmed that the probes can be used in living cells. These probes offer great practical advantages, including high sensitivity and rapid response (due to regulation of fluorescence at a single reactive site), as well as resistance to photobleaching, and are expected to be useful for a range of biological and pathological investigations.

  DOI：

  10.1021/ja309688m
• 作为产物：
  描述：

  rhodamine 123 在 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.84h， 生成 9H-fluoren-9-ylmethyl N-(6'-aminospiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl)carbamate
  参考文献：
  名称：

  Fluorescent probe for high-sensitivity pancreatic fluid detection, and method for detecting pancreatic fluid

  摘要：

  下面是表示为以下公式（I）的化合物或其盐的胰液检测用荧光探针。 （在公式中，A代表氨基酸残基或N-取代氨基酸残基，其中A与公式中相邻的NH形成酰胺键；R1代表氢原子或与苯环结合的1至4个相同或不同的取代基团；R2、R3、R4、R5、R6和R7分别独立地代表氢原子、羟基、烷基或卤素原子；R8和R9分别独立地代表氢原子或烷基；X代表C1-C3烷基基团）。

  公开号：

  US09506102B2

文献信息

• US9506102B2
  申请人：——

  公开号：US9506102B2

  公开（公告）日：2016-11-29