4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-(4-nitrophenyl)methylidene]-3,5-dimethylpyrrole | 883567-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-(4-nitrophenyl)methylidene]-3,5-dimethylpyrrole
• CAS: 883567-20-2
• 化学式: C₂₃H₂₇N₃O₂
• 分子量: 377.486
• InChiKey: QATJTNFABFGOLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  71.29
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-(4-nitrophenyl)methylidene]-3,5-dimethylpyrrole 在 palladium on carbon 、 三氟化硼乙醚 、 水 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 41.0h， 生成 4-[4-(2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)phenyl]ureidobenzoic acid O-succinimidyl ester
  参考文献：
  名称：

  Synthesis of Readily Accessible BODIPY-Based Fluorescence Derivatization Reagents for Amines

  摘要：

  Two BODIPY-based fluorescence derivatization reagents (FDRs) for amines were synthesized in a simple manner with practically acceptable yields via five steps. Both FDRs showed prompt reactivity, even against sterically hindered amines, to afford the corresponding FDR-labeled products in good yields. The solvent effect upon the fluorescence intensity of the derivatized amine was also investigated in a methanol-water binary solvent system to demonstrate that the strong fluorescence intensity was maintained in the solvent with a 0-60% water ratio. The detection limits of the new FDRs were estimated to be 20 fmol, which makes it much more sensitive than commercially available FDRs.

  DOI：

  10.3987/com-10-12031
• 作为产物：
  描述：

  对硝基苯甲醛 在 四氯苯醌 、 三氟乙酸 作用下， 生成 4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-(4-nitrophenyl)methylidene]-3,5-dimethylpyrrole
  参考文献：
  名称：

  Synthesis of Readily Accessible BODIPY-Based Fluorescence Derivatization Reagents for Amines

  摘要：

  Two BODIPY-based fluorescence derivatization reagents (FDRs) for amines were synthesized in a simple manner with practically acceptable yields via five steps. Both FDRs showed prompt reactivity, even against sterically hindered amines, to afford the corresponding FDR-labeled products in good yields. The solvent effect upon the fluorescence intensity of the derivatized amine was also investigated in a methanol-water binary solvent system to demonstrate that the strong fluorescence intensity was maintained in the solvent with a 0-60% water ratio. The detection limits of the new FDRs were estimated to be 20 fmol, which makes it much more sensitive than commercially available FDRs.

  DOI：

  10.3987/com-10-12031

文献信息

• Visible light excitable 3-formylBODIPYs for selective fluorescent and colorimetric sensing of cysteine
  作者：Qinghua Wu、Yangchun Wu、Min Zhang、Changjiang Yu、Erhong Hao、Lijuan Jiao

  DOI：10.1142/s1088424616500267

  日期：2016.1

  Selective fluorescent and colorimetric sensing of cysteine in methanol-HEPES buffer (45 mM, pH [Formula: see text] 7.2, v/v [Formula: see text] 1/1) solution over various common amino acids and related thiol containing compounds has been achieved based on the cyclization reaction between the formyl group on 3-formylBODIPYs and cysteine/homocystein. Upon addition of cysteine/homocystein, 3-formylBODIPYs

  甲醇-HEPES 缓冲液（45 mM，pH [公式：见文本] 7.2，v/v [公式：见文本] 1/1）溶液中半胱氨酸的选择性荧光和比色传感对各种常见氨基酸和相关的含硫醇化合物具有基于3-甲酰基BODIPYs上的甲酰基与半胱氨酸/同型半胱氨酸之间的环化反应实现。在添加半胱氨酸/同型半胱氨酸后，3-甲酰基 BODIPY 表现出显着增强的荧光强度以及吸收峰（20-30 nm）的明显红移。半胱氨酸的检出限在1.18~2.73[公式：见正文]10[公式：见正文]M。通过核磁共振和理论计算研究了检测机理。
• Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system
  作者：Yves Guminski、Martial Grousseaud、Sandrine Cugnasse、Viviane Brel、Jean-Philippe Annereau、Stéphane Vispé、Nicolas Guilbaud、Jean-Marc Barret、Christian Bailly、Thierry Imbert

  DOI：10.1016/j.bmcl.2009.03.052

  日期：2009.5

  The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N-1-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS. (c) 2009 Elsevier Ltd. All rights reserved.