2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehyde | 152105-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehyde
• 英文别名: 2-(1,3-Dioxobenzo[de]isoquinolin-2-yl)acetaldehyde
• CAS: 152105-19-6
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: CDOWXUSKFFVZEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehyde 、 正丁胺 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以85%的产率得到2-(2-(butylamino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  A 1,8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ion in living cells

  摘要：

  A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl) acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+ assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81 x 10(-6) M Cr3+ with an association constant, 15.9 x 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. H-1 NMR titration and DFT studies strongly support experimental findings.

  DOI：

  10.1016/j.jphotochem.2018.12.010
• 作为产物：
  描述：

  2-(2,2-dimethoxyethyl)-1H-benzo[d,e]isoquinoline-1,3(2H)-dione 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehyde
  参考文献：
  名称：

  A 1,8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ion in living cells

  摘要：

  A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl) acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+ assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81 x 10(-6) M Cr3+ with an association constant, 15.9 x 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. H-1 NMR titration and DFT studies strongly support experimental findings.

  DOI：

  10.1016/j.jphotochem.2018.12.010

文献信息

• Targeting ACE and ECE with dual acting inhibitors
  作者：Stephen Hanessian、Sébastien Guesné、Ludivine Riber、Julien Marin、Alain Benoist、Philippe Mennecier、Alain Rupin、Tony J. Verbeuren、Guillaume De Nanteuil

  DOI：10.1016/j.bmcl.2007.12.013

  日期：2008.2

  A series of urea analogues related to SA6817 and a GSK phosphonic acid with reported ACE inhibitory activity were prepared and tested for dual ACE and ECE activities. Although excellent ACE and NEP inhibition was achieved, only modest ECE inhibition was observed with one analogue. (C) 2008 Published by Elsevier Ltd.
• PHOSPHONOPEPTIDES WITH COLLAGENASE INHIBITING ACTIVITY
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0612324A1

  公开（公告）日：1994-08-31
• [EN] PHOSPHONOPEPTIDES WITH COLLAGENASE INHIBITING ACTIVITY
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1993009136A1

  公开（公告）日：1993-05-13

  (EN) Phosphorus derivatives having structure (I), processes for their preparation and their use as collagenase inhibitors.(FR) L'invention concerne des dérivés de phosphore possédant la structure (I), les procédés de préparation de ceux-ci et leur utilisation en tant qu'inhibiteurs de la collagénase.
• A 1,8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ion in living cells
  作者：Susanta Adhikari、Sabyasachi Ta、Avijit Ghosh、Subhajit Guria、Abhishek Pal、Manisha Ahir、Arghya Adhikary、Sumit Kumar Hira、Partha Pratim Manna、Debasis Das

  DOI：10.1016/j.jphotochem.2018.12.010

  日期：2019.3

  A 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetaldehydeanchored rhodamine B based probe, RDNAP detects Cr3+ ion by fluorescence resonance energy transfer (FRET) process in aqueous buffered acetonitrile media (7:3, v/v). Conversely, conjugation of 2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl) acetaldehyde with rhodamine B provides another probe, RDNAP-PY that undergoes Cr3+ assisted ratiometric fluorescence and colorimetric change in the same media. RDNAP-PY provides higher FRET efficiency and detects as low as 1.81 x 10(-6) M Cr3+ with an association constant, 15.9 x 104 M-1. Other common ions do not interfere. RDNAP-PY efficiently images intracellular Cr3+ in live Hep3B, MCF-7, HeLa, SiHa and HEK 293T cells under fluorescence microscope in a ratiometric and time dependent manner. H-1 NMR titration and DFT studies strongly support experimental findings.