N-phenyl-N-(5-phenyliminopenta-1,3-dienyl)acetamide | 728023-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-N-(5-phenyliminopenta-1,3-dienyl)acetamide
• CAS: 728023-20-9
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: UWDFGJIHGSWEAX-UHFFFAOYSA-N

物化性质

• 沸点：
  453.6±41.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-N-(5-phenyliminopenta-1,3-dienyl)acetamide 、 2,3,3-trimethyl-1-benzyl-indolium bromide 在 sodium acetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以78 mg的产率得到1,1'-dibenzyl-3,3,3',3'-tetramethylindotricarbocyanine bromide
  参考文献：
  名称：

  Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes

  摘要：

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.

  DOI：

  10.1021/ja910090v
• 作为产物：
  描述：

  5-anilino-penta-2,4-dienal-phenylimine 、 乙酸酐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-phenyl-N-(5-phenyliminopenta-1,3-dienyl)acetamide
  参考文献：
  名称：

  Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes

  摘要：

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.

  DOI：

  10.1021/ja910090v

文献信息

• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF INDOCYANINE GREEN<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE VERT D'INDOCYANINE
  申请人：DISHMAN PHARMACEUTICALS AND CHEMICALS LTD

  公开号：WO2017093889A1

  公开（公告）日：2017-06-08

  The present invention involves an improved process for the preparation of Indocyanine green of Formula (I) having high purity of about 99%, wherein the process comprises steps of reacting 1,1,2-trimethyl-1H-benzo[e]indole with 1,4-butane sulfone in boiling solvent to give 4-(1,1,2-trimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate. Followed by reacting 4-(1,1,2-trimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate of Formula (IV) and N-phenyl-N-((1E,3E,5E)-5-(phenylimino)penta-1,3-dienyl)acetamide of formula (V) in presence of sodium acetate and alcohol; and extracting the title compound formula (I) with an ester solvent.

  该发明涉及一种改进的工艺，用于制备具有约99%高纯度的分子式为(I)的吲哚青绿，其中该工艺包括以下步骤：在沸腾的溶剂中将1,1,2-三甲基-1H-苯并[e]吲哚与1,4-丁烷砜反应，得到4-(1,1,2-三甲基-1H-苯并[e]吲哚-3-基)丁烷-1-砜酸盐。接着，在存在醋酸钠和醇的情况下，将分子式为(IV)的4-(1,1,2-三甲基-1H-苯并[e]吲哚-3-基)丁烷-1-砜酸盐和分子式为(V)的N-苯基-N-((1E,3E,5E)-5-(苯基亚胺)戊-1,3-二烯基)乙酰胺反应；最后，用酯溶剂提取所述的目标化合物分子式(I)。
• Defect-engineered porphyrinic metal–organic framework nanoparticles for targeted multimodal cancer phototheranostics
  作者：Chenyuan Wang、Chuxiao Xiong、Zhike Li、Liefeng Hu、Jianshuang Wei、Jian Tian

  DOI：10.1039/d0cc07903k

  日期：——

  fabricated with an in situ one-pot protocol using cypate as the co-ligand and modulator. This multifunctional nanoplatform integrated the photothermal and multimodal imaging properties of cypate with the photodynamic effects of porphyrins, thus achieving targeted multimodal cancer phototheranostics after folic acid modification.

  缺陷工程化的卟啉MOF纳米粒子是使用cypate作为共配体和调节剂的原位一锅法制备的。这种多功能的纳米平台整合了细胞色素的光热和多峰成像特性与卟啉的光动力效应，从而在叶酸修饰后实现了靶向的多峰癌症光热疗。
• DIAGNOSING AND TREATING CANCER
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US20160220703A1

  公开（公告）日：2016-08-04

  The invention relates to compositions and methods for diagnosing as well as treating cancer diseases associated with choline kinase (ChoK). Specifically, the invention relates to a composition comprising an intrinsically fluorescent choline kinase (ChoK) inhibitor or a ChoK inhibitor operably linked to a fluorescent dye. The composition is capable of diagnosing and/or treating cancer diseases associated with ChoK.

  本发明涉及与胆碱激酶（ChoK）相关的癌症疾病的诊断和治疗的组合物和方法。具体而言，本发明涉及一种组合物，其包括本质上荧光的胆碱激酶（ChoK）抑制剂或与荧光染料操作性地连接的ChoK抑制剂。该组合物能够诊断和/或治疗与ChoK相关的癌症疾病。
• Process for the preparation of indocyanine green
  申请人：DISHMAN CARBOGEN AMCIS LIMITED

  公开号：US10287436B2

  公开（公告）日：2019-05-14

  The present invention involves an improved process for the preparation of Indocyanine green of Formula (I) having high purity of about 99%, wherein the process comprises steps of reacting 1,1,2-trimethyl-1H-benzo[e]indole with 1,4-butane sulfone in boiling solvent to give 4-(1,1,2-trimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate. Followed by reacting 4-(1,1,2-trimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate of Formula (IV) and N-phenyl-N-((1E,3E,5E)-5-(phenylimino)penta-1,3-dienyl)acetamide of formula (V) in presence of sodium acetate and alcohol; and extracting the title compound formula (I) with an ester solvent.

  本发明涉及一种制备纯度高达约 99% 的式 (I) 靛青绿的改进工艺，其中该工艺包括以下步骤：1,1,2-三甲基-1H-苯并[e]吲哚与 1,4-丁烷砜在沸腾溶剂中反应，得到 4-(1,1,2-三甲基-1H-苯并[e]吲哚鎓-3-基)丁烷-1-磺酸酯。然后将式（IV）的 4-(1,1,2-三甲基-1H-苯并[e]吲哚鎓-3-基)丁烷-1-磺酸与式（V）的 N-苯基-N-((1E,3E,5E)-5-(苯基亚氨基)戊-1,3-二基)乙酰胺在乙酸钠和乙醇存在下反应，并用酯类溶剂萃取式（I）的标题化合物。
• AN IMPROVED PROCESS FOR THE PREPARATION OF INDOCYANINE GREEN
  申请人：Dishman Pharmaceuticals And Chemicals Limited

  公开号：EP3383436A1

  公开（公告）日：2018-10-10