cyanofamoxadone | 1322705-18-9

• 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: cyanofamoxadone
• 英文别名: 4-[[5-Methyl-2,4-dioxo-5-(4-phenoxyphenyl)-1,3-oxazolidin-3-yl]amino]benzonitrile
• CAS: 1322705-18-9
• 化学式: C₂₃H₁₇N₃O₄
• 分子量: 399.406
• InChiKey: IFLCIGGNSACPFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 2-hydroxy-2-(4-phenoxyphenyl)propionate 在 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 cyanofamoxadone
  参考文献：
  名称：

  Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors

  摘要：

  The cytochrome bc(1) complex (EC 1.10.2.2, bc(1)) is one of the most promising targets for new drugs and agricultural fungicides. Among the existing bc(1) complex inhibitors specifically binding to the Q(o) site, oxazolidinedione derivatives have attracted great attention. With the aim to understand the substituent effects of oxazolidinedione derivatives on the inhibition activity against the bc(1) complex, a series of new oxazolidinedione derivatives were designed, synthesized, and biologically evaluated. The further inhibitory kinetics studies against porcine succinate-cytochrome c reductase (SCR) revealed that the representative compound 8d and famoxadone are both non-competitive inhibitors with respect to the substrate cytochrome c, but competitive inhibitors with respect to substrate decylubiquinol (DBH2). In addition, compound 8d and famoxadone showed, respectively, 35-fold and 15-fold greater inhibitory activity against the porcine SCR than the porcine bc(1) complex, indicating that these two inhibitors not only inhibited the activity of the bc(1) complex, but possibly affect the interaction between the complex II and the bc(1) complex. To our knowledge, this is the first report that famoxadone and its analogs have effects on the interaction between the complex II and the bc(1) complex. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.008

文献信息

• [EN] REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION<br/>[FR] RÉACTIFS ET PROCÉDÉ POUR LA FONCTIONNALISATION DIRECTE DE LA LIAISON C-H
  申请人：STUDIENGESELLSCHAFT KOHLE MBH

  公开号：WO2020094673A1

  公开（公告）日：2020-05-14

  Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

  Thianthrene衍生物的化学式（I）：其中R1到R8可以相同也可以不同，并且选择自氢、Cl、F、部分或完全氟化的C1到C6烷基基团，其中n为0或1，但R1到R8中至少有一个不是氢，并且使用该化合物进行芳香化合物的C-H官能团化的方法。
• Site-selective and versatile aromatic C−H functionalization by thianthrenation
  作者：Florian Berger、Matthew B. Plutschack、Julian Riegger、Wanwan Yu、Samira Speicher、Matthew Ho、Nils Frank、Tobias Ritter

  DOI：10.1038/s41586-019-0982-0

  日期：2019.3

  variety of well-defined arene derivatives. Here we report a highly selective aromatic C–H functionalization reaction that does not require a particular directing group or substitution pattern to achieve selectivity, and provides functionalized arenes that can participate in various transformations. We introduce a persistent sulfur-based radical to functionalize complex arenes with high selectivity and obtain

  直接 C–H 功能化可以快速增加有用的结构和功能分子复杂性 1-3。有时可以通过适当的导向基团或取代模式来实现位点选择性 1-4——在没有这种功能的情况下，大多数芳香族 C-H 官能化反应为大多数底物提供不止一种产物异构体 1,4,5。开发具有高位置选择性的 C-H 官能化反应，并安装一个官能团，该官能团可作为合成的关键以进一步官能化，这将提供获得多种明确定义的芳烃衍生物的途径。在这里，我们报告了一种高度选择性的芳族 C-H 官能化反应，它不需要特定的导向基团或取代模式来实现选择性，并提供可以参与各种转化的功能化芳烃。我们引入了一种持久的硫基自由基，以高选择性对复杂的芳烃进行功能化，并通过过渡金属和光氧化还原催化获得准备进行不同转化的铪盐。这种转化与之前所有芳香族 C-H 官能化反应的根本不同之处在于，它提供了对复杂小分子的大量衍生物的直接访问，快速生成具有其他方法无法实现的选择性的功能多
• Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts
  作者：Guofu Zhang、Zijin Luo、Chenfei Guan、Xianghao Zhang、Chengrong Ding

  DOI：10.1021/acs.joc.3c00814

  日期：2023.7.7

  Here, we report the first case of nickel-catalyzed C–H cyanation via arylthianthrenium salts. The reaction features the use of air-stable and inexpensive NiCl2·6H2O as a catalyst for the highly selective construction of cyanation products by aromatic pre-thianthrenation. The mechanism study shows that the formation of aryl radicals is involved. Also, this protocol can be applied to the late-stage functionalization

  在这里，我们报告了第一例通过芳基噻铼盐进行镍催化的 C-H 氰化反应。该反应的特点是使用空气稳定且廉价的NiCl 2 ·6H 2 O作为催化剂，通过芳族预噻虫胺化高选择性地构建氰化产物。机理研究表明涉及芳基自由基的形成。此外，该协议还可应用于生物活性分子的后期功能化，并且易于扩展，进一步展示了合成实用性。
• REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION
  申请人：Studiengesellschaft Kohle mbH

  公开号：EP3650446A1

  公开（公告）日：2020-05-13

  The present invention refers to a process for direct C-H functionalization, the reagents used in the process and the use thereof for the direct C-H functionalization as well as the so-obtained products.

  本发明涉及一种直接 C-H 功能化工艺、该工艺中使用的试剂、其在直接 C-H 功能化中的用途以及由此获得的产品。
• Design, syntheses, and kinetic evaluation of 3-(phenylamino)oxazolidine-2,4-diones as potent cytochrome bc1 complex inhibitors
  作者：Fu Wang、Hui Li、Le Wang、Wen-Chao Yang、Jia-Wei Wu、Guang-Fu Yang

  DOI：10.1016/j.bmc.2011.06.008

  日期：2011.8

  The cytochrome bc(1) complex (EC 1.10.2.2, bc(1)) is one of the most promising targets for new drugs and agricultural fungicides. Among the existing bc(1) complex inhibitors specifically binding to the Q(o) site, oxazolidinedione derivatives have attracted great attention. With the aim to understand the substituent effects of oxazolidinedione derivatives on the inhibition activity against the bc(1) complex, a series of new oxazolidinedione derivatives were designed, synthesized, and biologically evaluated. The further inhibitory kinetics studies against porcine succinate-cytochrome c reductase (SCR) revealed that the representative compound 8d and famoxadone are both non-competitive inhibitors with respect to the substrate cytochrome c, but competitive inhibitors with respect to substrate decylubiquinol (DBH2). In addition, compound 8d and famoxadone showed, respectively, 35-fold and 15-fold greater inhibitory activity against the porcine SCR than the porcine bc(1) complex, indicating that these two inhibitors not only inhibited the activity of the bc(1) complex, but possibly affect the interaction between the complex II and the bc(1) complex. To our knowledge, this is the first report that famoxadone and its analogs have effects on the interaction between the complex II and the bc(1) complex. (C) 2011 Elsevier Ltd. All rights reserved.