1-(2-(4-cyanophenyl)-2-oxoethyl)pyridin-1-ium bromide | 164580-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(4-cyanophenyl)-2-oxoethyl)pyridin-1-ium bromide
• 英文别名: 1-(2-(4-Cyano-phenyl)-2-oxo-ethyl)-pyridinium bromide；4-(2-pyridin-1-ium-1-ylacetyl)benzonitrile;bromide
• CAS: 164580-29-4
• 化学式: Br*C₁₄H₁₁N₂O
• 分子量: 303.158
• InChiKey: WJWWPWVHQKOSSM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(4-cyanophenyl)-2-oxoethyl)pyridin-1-ium bromide 在 草酰氯 、 ammonium acetate 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthetic molecules for disruption of the MYC protein-protein interface

  摘要：

  MYC is a key transcriptional regulator involved in cellular proliferation and has established roles in transcriptional elongation and initiation, microRNA regulation, apoptosis, and pluripotency. Despite this prevalence, functional chemical probes of MYC function at the protein level have been limited. Previously, we discovered 5a, that binds to MYC with potency and specificity, downregulates the transcriptional activities of MYC and shows efficacy in vivo. However, this scaffold posed intrinsic pharmacokinetic liabilities, namely, poor solubility that precluded biophysical interrogation. Here, we developed a screening platform based on field-effect transistor analysis (Bio-FET), surface plasmon resonance (SPR), and a microtumor formation assay to analyze a series of new compounds aimed at improving these properties. This blind SAR campaign has produced a new lead compound of significantly increased in vivo stability and solubility for a 40-fold increase in exposure. This probe represents a significant advancement that will not only enable biophysical characterization of this interaction and further SAR, but also contribute to advances in understanding of MYC biology.

  DOI：

  10.1016/j.bmc.2018.07.019
• 作为产物：
  描述：

  吡啶 、 2-溴-4'-氰基苯乙酮 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 1-(2-(4-cyanophenyl)-2-oxoethyl)pyridin-1-ium bromide
  参考文献：
  名称：

  一种高效的微波加速苯甲酰叠氮化物和吡啶鎓苯甲酰盐的三组分反应：2-amino-2-ene-1,4-diones/pyrrolidin-2-ones 的简便环保方法

  摘要：

  摘要 2-氨基-2-烯-1,4-二酮的温和有效的碱促进、微波辅助、绿色合成描述了通过苯甲酰叠氮化物的分解，然后用苯甲酰溴的吡啶鎓盐在水性介质中处理。各种带有电子释放和吸电子取代基的底物都具有良好的耐受性，并以良好的产率提供相应的 2-amino-2-ene-1,4-diones。合成的 2-amino-2-ene-1,4-diones 已在各种取代的 4-hydroxypyrrolidin-2-ones 的合成中得到进一步探索。图形概要

  DOI：

  10.1080/00397911.2020.1787447

文献信息

• Base-mediated 1,3-dipolar cycloaddition of pyridinium bromides with bromoallyl sulfones: a facile access to indolizine scaffolds
  作者：Chetna Jadala、Velma Ganga Reddy、Namballa Hari Krishna、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1039/d0ob01696a

  日期：——

  synthetic strategy has been developed for the construction of substituted indolizines from a unique combination of pyridinium salts and 2-bromoallyl sulfones. This approach does not compromise with the diverse substitutions on both the pyridinium salts and 2-bromoallyl sulfones. Wide substrate scope, operational simplicity, milder reaction conditions and good to moderate yields are the merits associated with

  已经开发了一种权宜且不含过渡金属的合成策略，用于从吡啶鎓盐和 2-溴烯丙基砜的独特组合构建取代的中氮茚。这种方法不会与吡啶鎓盐和 2-溴代烯丙基砜的多种取代相妥协。广泛的底物范围、操作简单、较温和的反应条件和良好至中等的产率是与当前方法相关的优点。此外，该方法提供了两种产品，它们适用于生成关键中氮茚构建块库。
• [EN] SMALL MOLECULE C-MYC INHIBITORS<br/>[FR] PETITES MOLÉCULES INHIBITRICES DE C-MYC
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2015089180A1

  公开（公告）日：2015-06-18

  This invention provides small molecule Myc-inhibitors. Also provided in the invention are therapeutic applications of these compounds for treating Myc-driven cancer and other related methods.

  这项发明提供了小分子Myc抑制剂。该发明还提供了这些化合物的治疗应用，用于治疗Myc驱动的癌症和其他相关方法。
• Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines
  作者：Yan Chen、Andrey Shatskiy、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.orglett.1c02754

  日期：2021.10.1

  regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonati

  报道了一种前所未有的银促进的区域选择性 (4 + 1) 异氰乙酸酯与吡啶盐的环化。已建立的协议提供对一系列合成有用的 N-稠合杂环支架的受控、简便和模块化访问，这些支架包含吲哚嗪、吡咯并 [1,2- a ] 喹啉、吡咯并 [2,1- a ] 异喹啉和 1 H -咪唑[4,5 - a ]indolizin-2(3 H )-ones。提出了涉及亲核加成/质子化/消除/环异构化的机制途径。
• Greener synthesis of indolizine analogues using water as a base and solvent: study for larvicidal activity against<i>Anopheles arabiensis</i>
  作者：Chandrashekharappa Sandeep、Katharigatta N. Venugopala、Raquel M. Gleiser、Abeen Chetram、Basavaraj Padmashali、Rashmi S. Kulkarni、Rashmi Venugopala、Bharti Odhav

  DOI：10.1111/cbdd.12823

  日期：2016.12

  Greener synthesis of a series of novel indolizine analogues have been achieved by the cyclization of aromatic cycloimmoniumylides with electron deficient alkynes in presence of water as the base and solvent at 80 degrees C. Yield of the title compounds was good and reactions performed were eco-friendly. The structures of these newly synthesized compounds have been confirmed by spectroscopic techniques

  通过在水为基础和溶剂存在下于80摄氏度下用缺电子炔烃将芳族环亚铵盐环化，可以实现一系列新型吲哚嗪类似物的绿色合成。标题化合物的收率良好，反应生态友好。这些新合成的化合物的结构已通过光谱技术（例如FTIR，NMR，LC-MS和元素分析）进行了确认。通过标准的WHO杀幼虫试验，以4杯/毫升的Temephos作为标准品，评估了表征的标题化合物对阿拉伯按蚊的杀幼虫活性。标题化合物2e，2f和2g作为有前途的杀幼虫剂出现。本文受版权保护。版权所有。
• DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes
  作者：Xinwei He、Ruxue Li、Pui Ying Choy、Tianyi Liu、Junya Wang、On Ying Yuen、Man Pan Leung、Yongjia Shang、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.0c03374

  日期：2020.12.18

  With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the −Br group

  通过邻位AQM（由炔丙基胺原位生成）和酰基卡宾替代物（由吡啶鎓内鎓盐）之间的串联DMAP催化反应，可以高收率组装各种聚芳基苯并二甲基苯酮。该方法不需要过渡金属催化剂，并且表现出对芳烃基团的容易操纵和良好的官能团相容性，特别是-Br基团，其可以通过交叉偶联反应进一步转化为其他官能团。o- AQM基板的模块化功能和简单的操作程序为该合成方法增加了更多优势。