1-iodo-2-nitro-4-phenylethynyl-benzene | 518980-39-7

• 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: 1-iodo-2-nitro-4-phenylethynyl-benzene
• 英文别名: 1-Iodo-2-nitro-4-(2-phenylethynyl)benzene
• CAS: 518980-39-7
• 化学式: C₁₄H₈INO₂
• 分子量: 349.128
• InChiKey: BNXWFQLBWAGLIT-UHFFFAOYSA-N

物化性质

• 沸点：
  424.2±40.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-iodo-2-nitro-4-phenylethynyl-benzene 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 三光气 、 三苯胂 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 4'-(4-isocyano-phenylethynyl)-2-nitro-4-phenylethynyl-biphenyl
  参考文献：
  名称：

  Biphenyl- and fluorenyl-based potential molecular electronic devices

  摘要：

  New potential molecular electronics devices have been synthesized based on our knowledge of systems that we previously studied. Research has shown that simple molecular systems demonstrate negative differential resistance (NDR) and memory characteristics. The new molecules rely primarily on the redox properties of the compounds to improve upon the solid-state characteristics already observed. Electrochemical tests have been performed in order to evaluate the redox properties with the hope that the electrochemical results can be used as a predictive tool to evaluate the usefulness of those compounds in device configurations. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00334-x
• 作为产物：
  描述：

  2-nitro-4-phenylethynyl-phenylamine 在 nitrosonium tetrafluoroborate 、 碘 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85%的产率得到1-iodo-2-nitro-4-phenylethynyl-benzene
  参考文献：
  名称：

  Synthesis of nitrile-terminated potential molecular electronic devices

  摘要：

  Several potential molecular devices have been synthesized consisting of oligo(phenylene ethynylene) (OPE) backbones containing a terminal nitrile group alligator clip as a means of attachment to a metal surface. The synthesis of four new nitrile-containing OPEs is discussed, including an improved synthesis of an intermediate used in our prior production of OPEs containing acetate-protected thiol alligator clips. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01527-2

文献信息

• [EN] TARGETING THE ONCOPROTEIN NUCLEOPHOSMIN<br/>[FR] CIBLAGE DE L'ONCOPROTÉINE NUCLÉOPHOSMINE
  申请人：HARVARD COLLEGE

  公开号：WO2009020768A1

  公开（公告）日：2009-02-12

  (+)-Avrainvillamide, a naturally occurring alkaloid with antiproliferative activity, is shown to bind to the oncoprotein nucleophosmin. Nucleophosmin is known to regulate the tumor suppressor protein p53 and is overexpressed in many different human tumors. The invention provides methods of modulating nucleophosmin and p53 using (+)-avrainvillamide and analogues thereof. These compounds may provide leads for the development of novel anti-cancer therapies that target nucleophosmin.

  （+）-Avrainvillamide，一种天然存在的具有抗增殖活性的生物碱，已被证明与致癌蛋白核仁磷蛋白结合。核仁磷蛋白已知调节肿瘤抑制蛋白p53，并在许多不同的人类肿瘤中过度表达。该发明提供了使用（+）-Avrainvillamide及其类似物调节核仁磷蛋白和p53的方法。这些化合物可能为针对核仁磷蛋白的新型抗癌疗法的开发提供线索。
• The Natural Product Avrainvillamide Binds to the Oncoprotein Nucleophosmin
  作者：Jeremy E. Wulff、Romain Siegrist、Andrew G. Myers

  DOI：10.1021/ja075327f

  日期：2007.11.1

  (+)-avrainvillamide, a naturally occurring alkaloid with antiproliferative effects, binds to the nuclear chaperone nucleophosmin, a proposed oncogenic protein that is overexpressed in many different human tumors. Among other effects, nucleophosmin is known to regulate the tumor suppressor protein p53. A synthetic biotin-avrainvillamide conjugate, nearly equipotent to the natural product in inhibiting the growth

  在这里，我们提供的证据表明，(+)-avrainvillamide 是一种具有抗增殖作用的天然生物碱，可与核伴侣核磷蛋白结合，这是一种在许多不同的人类肿瘤中过度表达的致癌蛋白。除其他作用外，已知核磷蛋白可调节肿瘤抑制蛋白 p53。合成生物素-avrainvillamide 缀合物在抑制培养的 T-47D 细胞生长方面几乎与天然产物等效，用于亲和分离通过 MS 测序和蛋白质印迹鉴定为核磷蛋白的蛋白质。在碘乙酰胺 (10 mM)、游离 (+)-avrainvillamide (100 microM) 和一系列密切相关的 (+)-avrainvillamide 结构类似物的存在下，核磷蛋白的亲和分离受到抑制，后者具有抑制作用，似乎与测量的生长抑制效力相关。使用荧光显微术，观察到合成丹磺酰-avrainvillamide 缀合物定位于处理过的癌细胞的核仁和细胞质内。在 COS-7 细胞中与天然核磷
• TARGETING THE ONCOPROTEIN NUCLEOPHOSMIN
  申请人：Myers Andrew G.

  公开号：US20110105515A1

  公开（公告）日：2011-05-05

  (+)-Avrainvillamide, a naturally occurring alkaloid with antiproliferative activity, is shown to bind to the oncoprotein nucleophosmin. Nucleophosmin is known to regulate the tumor suppressor protein p53 and is overexpressed in many different human tumors. The invention provides methods of modulating nucleophosmin and p53 using (+)-avrainvillamide and analogues thereof. These compounds may provide leads for the development of novel anti-cancer therapies that target nucleophosmin.

  根据您的请求，我将把这段英文文本翻译成中文： (+)-Avrainvillamide是一种天然存在的具有抗增殖活性的生物碱，已被证明能够与致癌蛋白核仁素结合。核仁素已知调控肿瘤抑制蛋白p53，并且在许多不同的人类肿瘤中过度表达。本发明提供了使用(+)-Avrainvillamide及其衍生物调节核仁素和p53的方法。这些化合物可能为开发靶向核仁素的新型抗癌疗法提供线索。
• Improved and new syntheses of potential molecular electronics devices
  作者：David W Price、Shawn M Dirk、Francisco Maya、James M Tour

  DOI：10.1016/s0040-4020(03)00246-1

  日期：2003.3

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.