4-(dicyanomethylene)-4H-1-benzopyran-2-methyl-2-indole-3-carboxamide | 1352173-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(dicyanomethylene)-4H-1-benzopyran-2-methyl-2-indole-3-carboxamide
• 英文别名: 2-[2-[2-(1H-indol-3-yl)ethenyl]chromen-4-ylidene]propanedinitrile
• CAS: 1352173-01-3
• 化学式: C₂₂H₁₃N₃O
• 分子量: 335.365
• InChiKey: SAPLEOFUXHLVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基色原酮 在 哌啶 、 乙酸酐 作用下， 以 乙腈 为溶剂， 生成 4-(dicyanomethylene)-4H-1-benzopyran-2-methyl-2-indole-3-carboxamide
  参考文献：
  名称：

  Development of FluoAHRL: A Novel Synthetic Fluorescent Compound That Activates AHR and Potentiates Anti-Inflammatory T Regulatory Cells

  摘要：

  Aryl Hydrocarbon Receptor (AHR) ligands, upon binding, induce distinct gene expression profiles orchestrated by the AHR, leading to a spectrum of pro- or anti-inflammatory effects. In this study, we designed, synthesized and evaluated three indole-containing potential AHR ligands (FluoAHRL: AGT-4, AGT-5 and AGT-6). All synthesized compounds were shown to emit fluorescence in the near-infrared. Their AHR agonist activity was first predicted using in silico docking studies, and then confirmed using AHR luciferase reporter cell lines. FluoAHRLs were tested in vitro using mouse peritoneal macrophages and T lymphocytes to assess their immunomodulatory properties. We then focused on AGT-5, as it illustrated the predominant anti-inflammatory effects. Notably, AGT-5 demonstrated the ability to foster anti-inflammatory regulatory T cells (Treg) while suppressing pro-inflammatory T helper (Th)17 cells in vitro. AGT-5 actively induced Treg differentiation from naïve CD4+ cells, and promoted Treg proliferation, cytotoxic T-lymphocyte-associated antigen 4 (CTLA-4) expression and interleukin-10 (IL-10) production. The increase in IL-10 correlated with an upregulation of Signal Transducer and Activator of Transcription 3 (STAT3) expression. Importantly, the Treg-inducing effect of AGT-5 was also observed in human tonsil cells in vitro. AGT-5 showed no toxicity when applied to zebrafish embryos and was therefore considered safe for animal studies. Following oral administration to C57BL/6 mice, AGT-5 significantly upregulated Treg while downregulating pro-inflammatory Th1 cells in the mesenteric lymph nodes. Due to its fluorescent properties, AGT-5 could be visualized both in vitro (during uptake by macrophages) and ex vivo (within the lamina propria of the small intestine). These findings make AGT-5 a promising candidate for further exploration in the treatment of inflammatory and autoimmune diseases.

  DOI：

  10.3390/molecules29132988

文献信息

• The synthesis and spectral properties of a stimuli-responsive D–π–A charge transfer dye based on indole donor and dicyanomethylene acceptor moiety
  作者：Yu Wang、Seon-Yeong Gwon、Sheng Wang、Sung-Hoon Kim

  DOI：10.1016/j.saa.2011.10.039

  日期：2012.2

  A dual mode chemosensor dye 3 for detection of fluoride ion, based on the D-π-A molecular framework by one-step condensation, presents high selectivity and sensitivity both in colorimetric and fluorometric analyses. Upon the addition of F(-) anion, the absorption band shows a remarkable red shift along with fluorescent intensity decreasing. The absorption and fluorescent intensities of the dye 3 can

  基于D-π-A分子框架通过一步缩合检测氟离子的双模式化学传感器染料3在比色和荧光分析中均具有很高的选择性和灵敏度。加入F（-）阴离子后，吸收带显示出明显的红移，同时荧光强度降低。染料3的吸收和荧光强度可通过控制分子内电荷转移（ICT）通过胺部分的去质子化/质子化而可逆地选择，从而导致分子开关处于“开”和“关”状态。（1）H NMR滴定分析和DMol（3）计算用于揭示染料3-F（-）配合物的分子间电荷转移系统。
• 수은 이온 검출용 염료 조성물
  申请人：Kyungpook National University Industry-Academic Cooperation Foundation 경북대학교 산학협력단(220040016844) BRN ▼504-82-09678

  公开号：KR101484697B1

  公开（公告）日：2015-01-20

  본 발명은 하기 화학식 1로 표시되는 화합물을 포함하는 수은 이온 검출용 조성물 및 이를 이용한 수은 이온 검출방법에 관한 것이다. 이에 따라, 하기 화학식 1로 표시되는 화합물은 수은 이온을 선택적으로 검출할 수 있어, 생물학계, 화학계 및 환경학계에 효과적인 수은 이온 감지용 염료로 제공할 수 있다. [화학식 1]

  本发明涉及一种含有化学式1所示化合物的汞离子检测组合物及其用于汞离子检测的方法。根据本发明，化学式1所示的化合物能够选择性地检测汞离子，因此可以作为一种有效的汞离子检测染料在生物学、化学和环境学领域中提供。[化学式1]