1-ethyl-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1H-benz[c,d]indole | 81903-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-ethyl-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1H-benz[c,d]indole
• 英文别名: 5-(1-Ethylbenzo[cd]indol-2-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 81903-56-2
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: WHPXLAHMLPLPNC-UHFFFAOYSA-N

物化性质

• 沸点：
  548.5±50.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethyl-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1H-benz[c,d]indole 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以84%的产率得到1-Ethyl-2-methyl-benzo[cd]indolium; bromide
  参考文献：
  名称：

  Mikhailenko, F. A.; Vasilenko, N. P.; Kachkovskii, A. D., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 2, p. 380 - 386

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(methylthio)benzindolium iodide 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-ethyl-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1H-benz[c,d]indole
  参考文献：
  名称：

  Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents

  摘要：

  Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.017

文献信息

• Site-specific albumin tagging with NIR-II fluorogenic dye for high-performance and super-stable bioimaging
  作者：Ningning Zhu、Jiajun Xu、Qi Su、Tianyang Han、Ding Zhou、Yuewei Zhang、Shoujun Zhu

  DOI：10.7150/thno.88815

  日期：——

  capable of site-specific albumin tagging for in situ albumin seeking/targeting or constructing high-performance cyanine@albumin probes. We further investigate the interaction mechanism between NIR-II fluorogenic dyes and albumin./nResults: We identify CO-1080 as an optimal dye structure that produces a stable/bright NIR-II cyanine@albumin probe. CO-1080 exhibits maximum supramolecular binding affinity

  合成的近红外 II （NIR-II） 染料有望用于深层组织成像，但它们通常难以以高特异性靶向给定的生物分子。此外，白蛋白和花青素分子之间的相互作用机制通常被认为是不确定的“复合物”，例如交联纳米颗粒，仍然知之甚少。方法：在这里，我们提出了一类新的NIR-II荧光染料，能够进行位点特异性白蛋白标记，用于原位白蛋白寻找/靶向或构建高性能cyanine@albumin探针。我们进一步研究了 NIR-II 荧光染料与白蛋白之间的相互作用机制。结果：我们确定 CO-1080 是一种最佳染料结构，可产生稳定/明亮的 NIR-II cyanine@albumin探针。CO-1080 在催化其共价连接时表现出对白蛋白的最大超分子结合亲和力。探针显示了位于 Cys476 和 Cys101 上的确切结合位点，通过蛋白质组学分析和对接建模确定。结论：我们的 cyanine@albumin 探针显著改善了其游离染料对应物的药代动力学，实现了高性能的
• CN116283726
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
  作者：Sarmistha Halder Sinha、Eric A. Owens、You Feng、Yutao Yang、Yan Xie、Yaping Tu、Maged Henary、Yujun George Zheng

  DOI：10.1016/j.ejmech.2012.06.017

  日期：2012.8

  Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Mikhailenko, F. A.; Vasilenko, N. P.; Kachkovskii, A. D., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 2, p. 380 - 386
  作者：Mikhailenko, F. A.、Vasilenko, N. P.、Kachkovskii, A. D.、Rozhinskii, Yu. I.

  DOI：——

  日期：——