2-(6-(4-(7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)piperazin-1-yl)-3-oxo-3H-xanthen-9-yl) benzoic acid

• 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-(4-(7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)piperazin-1-yl)-3-oxo-3H-xanthen-9-yl) benzoic acid
• 英文别名: 2-[3-[4-[7-(Diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]-6-oxoxanthen-9-yl]benzoic acid；2-[3-[4-[7-(diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]-6-oxoxanthen-9-yl]benzoic acid
• 化学式: C₃₈H₃₃N₃O₇
• 分子量: 643.696
• InChiKey: ZQKJFWZEUJHQGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(6-(4-(7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)piperazin-1-yl)-3-oxo-3H-xanthen-9-yl) benzoic acid 、 1-氯-2,4-二硝基苯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以85%的产率得到3'-[4-[7-(Diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]-6'-(2,4-dinitrophenoxy)spiro[2-benzofuran-3,9'-xanthene]-1-one
  参考文献：
  名称：

  Ratiometric and colorimetric detection of hydrogen sulfide with high selectivity and sensitivity using a novel FRET-based fluorescence probe

  摘要：

  With recognition of the biological significance of H2S, we have designed and synthesized a novel ratiometric and colorimetric fluorescence probe, CR-DNP based on a H2S induced thiolysis reaction as well as the fluorescence resonance energy transfer process. It displayed some desirable properties, such as good photostability, high selectivity and excellent sensitivity. Also, a considerably fluorescence enhancement (15-fold) and distinct visible color change (colorless to bright orange) was observed. A good linear relationship between the emission intensity ratios and NaHS concentrations suggested that it can detect H2S quantitatively with a detection limit as low as 0.4 mu M. Furthermore, due to its biocompatibility, the sensor could easily permeate through the cell membrane and trace the intracellular H2S levels change. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.03.007
• 作为产物：
  描述：

  7-(二乙胺基)香豆素-3-甲酸乙酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 生成 2-(6-(4-(7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)piperazin-1-yl)-3-oxo-3H-xanthen-9-yl) benzoic acid
  参考文献：
  名称：

  一种基于FRET的新型比例荧光探针，用于高灵敏度检测硫化氢†

  摘要：

  一种新的基于FRET的比率荧光探针ħ 2 S-CR为H的定量检测2 S为设计并合成。它的响应时间为20分钟，荧光信号增强显着（15倍），检测极限极低（19 nM）。它可以成功地应用于活细胞中H 2 S的成像。

  DOI：

  10.1039/c4ra16578k

文献信息

• Cascade reaction and FRET-based fluorescent probe for the colorimetric and ratiometric signaling of hydrogen sulfide
  作者：Kunzhu Huang、Meihui Liu、Xiaobo Wang、Dongsheng Cao、Feng Gao、Kechao Zhou、Wei Wang、Wenbin Zeng

  DOI：10.1016/j.tetlet.2015.04.054

  日期：2015.6

  A novel addition–elimination cascade reaction and FRET-based fluorescent probe for the colorimetric and ratiometric signaling of hydrogen sulfide was designed. Employing of 2-formylbenzoic acid as the trapper, the probe was highly selective and sensitive to H2S over other biologically relevant species to give color change from colorless to bright orange for naked eye observation. A linear response

  设计了一种新颖的加消除级联反应和基于FRET的荧光探针，用于硫化氢的比色和比例信号传递。使用2-甲酰基苯甲酸作为捕集剂，该探针具有高选择性，并且对H 2 S的敏感性高于其他生物学相关物种，从而可以从无色变为亮橙色，以进行肉眼观察。对H 2 S的线性响应在0-200μM范围内，表明它可以定量检测H 2 S，检出限低至0.39μM。此外，荧光倒置显微镜成像实验表明该探针可以评估细胞内H 2 S水平的变化。
• Accurate photoactivation monitoring <i>via</i> the construction of an intramolecular synergistic counteracting mechanism of FRET and IFE
  作者：Siyue Ma、Yihan Wang、Chao Wang、Linlin Wang、Qing Miao、Yuxia Liu、Yangmin Ma、Guang Chen

  DOI：10.1039/d3cc00951c

  日期：——

  We propose an intramolecular synergistic counteracting strategy of fluorescence resonance energy transfer and the inner filter effect for accurate photoactivation monitoring, to eliminate the influence of the biological microenvironment.

  我们提出了一种分子内荧光共振能量转移和内部滤光片效应的协同抵消策略，用于精确的光激活监测，以消除生物微环境的影响。
• 一种香豆素前药及其制备方法和用途
  申请人：中国药科大学

  公开号：CN115477657A

  公开（公告）日：2022-12-16

  本发明公开了一种香豆素前药及其制备方法和用途，该香豆素前药的化学结构如式(1)所示。本发明提供的香豆素前药在适当的条件下可以释放出H2S气体。该前药在405nm光照触发下释放出COS，经CA水解生成了 ，可以用于构建新型光控释放的硫化氢供体分子。