2-[(anthracen-9-ylmethylene)amino]ethanol | 414901-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-[(anthracen-9-ylmethylene)amino]ethanol
• 英文别名: 2-(Anthracen-9-ylmethylideneamino)ethanol
• CAS: 414901-43-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: GBFAJRLXDANYMO-UHFFFAOYSA-N

物化性质

• 沸点：
  469.1±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(anthracen-9-ylmethylene)amino]ethanol 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 toluene-4-sulfonic acid 2-[anthracen-9-ylmethyl-(toluene-4-sulfonyl)-amino]-ethyl ester
  参考文献：
  名称：

  Synthesis and Characterization of N¹-(4-Toluenesulfonyl)-N¹- (9-anthracenemethyl)triamines

  摘要：

  A modular synthetic approach was developed to access triamines with varying tether lengths from commercially available aminoalkanols. Initial N-alkylation via reductive amination with anthracene-9-carbaldehyde provided the secondary amines in good yield. Subsequent ditosylation with excess TsCl yielded the respective bis-N,O-tosylates. The tosylates were reacted with excess putrescine to give the final triamines. X-ray crystallography revealed that the polyamine tail is preferentially oriented over the shielding cone of the anthracene ring.

  DOI：

  10.1021/jo020331p
• 作为产物：
  描述：

  C.I.酸性橙108 、 9-蒽甲醛 以 甲醇 为溶剂， 生成 2-[(anthracen-9-ylmethylene)amino]ethanol
  参考文献：
  名称：

  蒽标记的吡啶酰胺受体中羟基在分子识别α-酮基和羟基一元羧酸中的作用

  摘要：

  为了确定羟基在羧酸识别中的作用，设计并合成了蒽标记的吡啶酰胺传感器1。该传感器用作α-酮酸和羟基酸的“开-关”荧光开关。使用1 H NMR，荧光和UV-vis光谱法研究了结合性能。传感器1对丙酮酸具有选择性。

  DOI：

  10.1016/j.tetlet.2006.10.140

文献信息

• Synthesis and properties of polymer chemosensors based on 1-vinylimidazole
  作者：Vladimir A. Bren、Ivan E. Tolpygin、Yurii V. Revinskii、Karina S. Tikhomirova、Alexander D. Dubonosov、Vladimir I. Minkin

  DOI：10.24820/ark.5550190.p010.625

  日期：——

  Derivatives of poly(1-vinylimidazolium chloride) possessing chemosensor properties to cations and anions were synthesized by quaternization of poly-(1-vinylimidazole) (PVI) (Mw ~ 63000) by alkylating compounds containing anthracene fluorophore. Poly(3-[2-(anthracen-9-ylmethyl)amino]ethyl}-1-vinylimidazolium chloride) demonstrates selectivity with more than a 20 fold increase in relative fluorescence

  通过聚（1-乙烯基咪唑）（PVI）（Mw ~ 63000）通过含有蒽荧光团的烷基化化合物季铵化合成对阳离子和阴离子具有化学传感器特性的聚（1-乙烯基咪唑氯化物）衍生物。聚(3-[2-(anthracen-9-ylmethyl)amino]ethyl}-1-vinylimidazolium chloride) 表现出选择性，在 Zn 阳离子存在下，相对荧光强度 I/I0 增加了 20 倍以上。聚（3-[2-（蒽-9-基甲基）（3,5-二氯苯基）氨基]-2-氧乙基}-1-乙烯基咪唑氯化物）作为 AcO 的化学传感器，改变其 DMSO 溶液的颜色淡黄色至亮橙色。
• Compounds and method for enhancing the efficacy of anti-cancer drugs
  申请人：University of Central Florida Research Foundation, Inc.

  公开号：US07001925B1

  公开（公告）日：2006-02-21

  Polyamine compounds, method of synthesis and method of use for anti-cancer purposes, and for enhancing the activity of existing anti-cancer drugs are provided. This disclosure has identified certain polyamine motifs that can be attached to toxic agents to facilitate their access to cancer cells as well as polyamine compounds of surprising cytotoxicity and selectivity in killing cancer cells. It includes an illustrative conjugate system with examples of a triamine or a tetraamine appended to a cytotoxic agent. There are five method schemes illustrative of the synthesis of the compounds of the invention. Included is a general strategy to enhance cell uptake by attaching a polyamine vectoring system with an example of a triamine vector attached to an existing anti-cancer drug to improve its chemotherapeutic potency. There is an illustration of using the triamine vector to improve the selectivity of an anthracenylmethyl amine cytotoxic agent (e.g. an anthracenylmethyl-4,4-triamine conjugate outperformed an anthracenylmethyl N-butyl amine derivative). There is an illustration of a synthetic method to attach the polyamine vector onto an existing chemotherapeutic, doxorubicin. This methodology can lead to the synthesis of the polyamine-doxorubicin conjugate. There are illustrations of the synthesis of various alkyl aryl substituted polyamines, a hydroxylated polyamine derivative and a cyclohexyldiamine analogue.

  提供了聚胺化合物、用于抗癌目的的合成方法和使用方法，以及用于增强现有抗癌药物活性的方法。本公开揭示了可以附着在毒性剂上的某些聚胺基团，以促进它们进入癌细胞，以及在杀灭癌细胞方面具有惊人细胞毒性和选择性的聚胺化合物。其中包括具有三胺或四胺附加到细胞毒性剂的示例的插图结合系统。有五种示例性的方法方案说明了本发明化合物的合成。其中包括通过附着聚胺引导系统来增强细胞摄取的一般策略，其中包括将三胺引导附着到现有抗癌药物以提高其化疗效力的示例。有一个示例说明了使用三胺引导来提高蒽甲基胺类细胞毒性剂的选择性（例如，蒽甲基-4,4-三胺共轭物优于蒽甲基N-丁基胺衍生物）。还有一个示例说明了一种合成方法，用于将聚胺引导附着到现有的化疗药物多柔比星上。这种方法可以导致聚胺-多柔比星共轭物的合成。还有合成各种烷基芳基取代的聚胺、羟基化聚胺衍生物和环己基二胺类似物的插图。
• Synthesis and Characterization of <i>N</i>¹-(4-Toluenesulfonyl)-<i>N</i>¹- (9-anthracenemethyl)triamines
  作者：Chaojie Wang、Khalil A. Abboud、Phanstiel

  DOI：10.1021/jo020331p

  日期：2002.11.1

  A modular synthetic approach was developed to access triamines with varying tether lengths from commercially available aminoalkanols. Initial N-alkylation via reductive amination with anthracene-9-carbaldehyde provided the secondary amines in good yield. Subsequent ditosylation with excess TsCl yielded the respective bis-N,O-tosylates. The tosylates were reacted with excess putrescine to give the final triamines. X-ray crystallography revealed that the polyamine tail is preferentially oriented over the shielding cone of the anthracene ring.
• Effect of a hydroxyl group in an anthracene-labelled pyridine amide receptor in molecular recognition of α-keto and hydroxy monocarboxylic acids
  作者：Kumaresh Ghosh、Goutam Masanta

  DOI：10.1016/j.tetlet.2006.10.140

  日期：2006.12

  the role of a hydroxyl group in carboxylic acid recognition, anthracene-labelled pyridine amide sensor 1 was designed and synthesized. The sensor functions as an ‘off–on’ fluorescence switch for α-keto and hydroxy acids. The binding properties were studied using 1H NMR, fluorescence and UV–vis spectroscopic methods. Sensor 1 is selective for pyruvic acid.

  为了确定羟基在羧酸识别中的作用，设计并合成了蒽标记的吡啶酰胺传感器1。该传感器用作α-酮酸和羟基酸的“开-关”荧光开关。使用1 H NMR，荧光和UV-vis光谱法研究了结合性能。传感器1对丙酮酸具有选择性。