ω-ethythio-p-bromoacetophenone | 13222-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ω-ethythio-p-bromoacetophenone
• 英文别名: 2-(4-bromophenyl)ethanonyl ethyl sulfide；p-bromo-2-(ethylthio)acetophenone；1-(4-bromophenyl)-2-(ethylthio)ethanone；1-(4-bromophenyl)-2-ethylsulfanylethanone
• CAS: 13222-37-2
• 化学式: C₁₀H₁₁BrOS
• 分子量: 259.167
• InChiKey: PGZOKBMCXDVQRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±27.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ω-ethythio-p-bromoacetophenone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙基苯 为溶剂， 反应 2.0h， 生成 (4-bromophenyl)ethynyl ethyl sulfide
  参考文献：
  名称：

  芳乙炔基硫化物和双(芳基乙炔基)硫化物的一锅法制备

  摘要：

  芳基乙炔基硫化物 1 和双（芳基乙炔基）硫化物 2 的有效制备已通过一锅三步策略完成，该策略分别从芳基乙炔基硫化物和双（芳基乙炔基）硫化物开始，无需使用各种末端芳基乙炔作为底物. 当将六甲基二硅氮烷锂 (LHMDS)、ClP(O)(OEt)2 和 LHMDS 依次加入不同底物 [芳基乙酮硫化物或双（芳基乙炔基）硫化物] 的四氢呋喃溶液中时，以中等至良好的收率获得 1 或 2。反应过程包括烯醇磷酸酯的形成和随后的碱诱导消除。

  DOI：

  10.1002/ejoc.201201422
• 作为产物：
  描述：

  4-溴苯乙酮 在 sodium methylate 、 copper(I) bromide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.08h， 生成 ω-ethythio-p-bromoacetophenone
  参考文献：
  名称：

  芳乙炔基硫化物和双(芳基乙炔基)硫化物的一锅法制备

  摘要：

  芳基乙炔基硫化物 1 和双（芳基乙炔基）硫化物 2 的有效制备已通过一锅三步策略完成，该策略分别从芳基乙炔基硫化物和双（芳基乙炔基）硫化物开始，无需使用各种末端芳基乙炔作为底物. 当将六甲基二硅氮烷锂 (LHMDS)、ClP(O)(OEt)2 和 LHMDS 依次加入不同底物 [芳基乙酮硫化物或双（芳基乙炔基）硫化物] 的四氢呋喃溶液中时，以中等至良好的收率获得 1 或 2。反应过程包括烯醇磷酸酯的形成和随后的碱诱导消除。

  DOI：

  10.1002/ejoc.201201422

文献信息

• Switching Reversibility to Irreversibility in Glycogen Synthase Kinase 3 Inhibitors: Clues for Specific Design of New Compounds
  作者：Daniel I. Perez、Valle Palomo、Concepción Pérez、Carmen Gil、Pablo D. Dans、F. Javier Luque、Santiago Conde、Ana Martínez

  DOI：10.1021/jm1016279

  日期：2011.6.23

  halomethylketone moiety to reversible inhibitors turned them into irreversible inhibitors with IC50 values in the nanomolar range. Overall, the results point out that these compounds might be useful pharmacological tools to explore physiological and pathological processes related to signaling pathways regulated by GSK-3 opening new avenues for the discovery of novel GSK-3 inhibitors.

  开发针对中枢神经系统（CNS）疾病的激酶靶向疗法是一项巨大的挑战。糖原合酶激酶3（GSK-3）在严重的中枢神经系统未满足疾病中具有巨大潜力，它是针对不同疾病的临床试验中的抑制剂之一。根据我们基于GSK-3结合位点残基Cys199的增强反应性的假设，我们在这里检查苯基卤代甲基酮作为不可逆抑制剂的适用性。我们的数据证实卤代甲基酮单元对于抑制活性是必不可少的。此外，在可逆抑制剂中添加卤代甲基酮部分可将其转变为具有IC 50的不可逆抑制剂值在纳摩尔范围内。总体而言，结果指出这些化合物可能是探索与GSK-3调节的信号通路相关的生理和病理过程的有用药理工具，为发现新型GSK-3抑制剂开辟了新途径。
• Reaction of ammonium ylides with alkyl thiocyanates in aqueous and non-aqueous media
  作者：Ebrahim Kianmehr、Mansoureh Mirza Agha、Hamid Estiri

  DOI：10.1007/s00706-010-0274-8

  日期：2010.4

  AbstractReaction of ammonium ylides with alkyl thiocyanates in aqueous and non-aqueous media is described. The reaction leads to alkyl thio-substituted acetophenones via addition of ammonium ylides to alkyl thiocyanates in organic solvents or in situ generated thiolate anions in aqueous media. Graphical abstract

  摘要描述了铵盐与烷基硫氰酸酯在水性和非水性介质中的反应。该反应通过在有机溶剂中向烷基硫氰酸酯中添加铵盐或在水性介质中原位生成的硫醇盐阴离子，将烷基硫基取代的苯乙酮生成烷基硫基取代的苯乙酮。 图形概要
• Carbon-13 NMR spectra of some 2- ethylthio-4′-substituted acetophenones and their mono- and di-oxygenated derivatives
  作者：Paulo Roberto Olivato、Élida Bonfada、Roberto Rittner

  DOI：10.1002/mrc.1260300116

  日期：1992.1

  The 13C NMR signals for some 2‐ethylthio‐, 2‐ethylsulphinyl‐ and 2‐ethylsulphonyl‐4′‐substituted acetophenones were assigned. The carbonyl carbons exhibit a progressive upfield shift on going from the ketosulphides to the ketosulphoxides and to the ketosulphones. The α‐methylene carbons fro the three classes of compounds are shielded by almost the same amount in relation to the corresponding calculated

  指定了一些 2-乙硫基-、2-乙基亚磺酰基-和 2-乙基磺酰基-4'-取代的苯乙酮的 13C NMR 信号。羰基碳在从酮硫化物到酮亚砜和酮砜的过程中表现出渐进的高场转移。与相应的计算值相比，三类化合物的 α-亚甲基碳被屏蔽的量几乎相同。芳环碳的化学位移与使用取代基化学位移计算的那些非常一致。
• Q39, a novel synthetic Quinoxaline 1,4-Di-N-oxide compound with anti-cancer activity in hypoxia
  作者：Qinjie Weng、Duoduo Wang、Peng Guo、Liang Fang、Yongzhou Hu、Qiaojun He、Bo Yang

  DOI：10.1016/j.ejphar.2007.12.006

  日期：2008.3

  Hypoxia is one of the inevitable circumstances in various tumors and results in tumor resistance to radiotherapy and chemotherapy. The present data showed that 3-(4-bromophenyl)-2-(ethylsulfonyl)-6-methylquinoxaline 1,4-dioxide (Q39), derived from Quinoxaline 1,4-Di-N-oxide, possessed high anti-cancer activity in hypoxia. Cytotoxicity assay demonstrated that Q39 is a potential and high efficient anti-cancer compound in all tested cell lines with IC50 values of 0.18 +/- 0.03-8.88 +/- 1.12 mu M in hypoxia and 0.33 +/- 0.04-8.74 +/- 1.28 mu M in normoxia. In the following work concerning the mechanism of Q39 in hypoxia, we confirmed that Q39 could cause the apoptosis of K562 cells in a time-dependent manner. By fluorescence stain assay, Q39-induced mitochondria membrane potential (Delta Psi(m)) loss was observed in K562 cells in hypoxia. Based on the western blotting, Q39 decreased the protein expression of hypoxia-inducible factor-1 alpha (HIF-1 alpha) and vascular endothelial growth factor (VEGF) in hypoxia. The compound caused the activation of caspase-3 and subsequent cleavage of its substrate poly (ADP-ribose) polymerase (PARP) in hypoxia. Meanwhile, we found the upregulation of Bax by Q39 in K562 cells as well as the downregulation of Bcl-2. Q39 also influenced the expression of Mitogen-Activated Protein Kinase (MAPKs) and other proteins relative to mitochondria induced apoptosis. In addition, Q39-mediated apoptosis was not reversed after treatment with the JNK-specific inhibitor. In summary, the present study demonstrated Q39 was a novel compound against cancer cells in hypoxia. The mitochondrial pathway mediated by Bcl-2 protein family and MAPKs and the HIF-1 pathway might be involved in signaling Q39-induced apoptosis. (C) 2007 Elsevier B.V. All rights reserved.
• Novel reactions of organic sulfur and selenium compounds with thallium(III) nitrate: sulfoxide and selenoxide formation and pummerer-like reaction
  作者：Yoshimitsu Nagao、Masahito Ochiai、Kimiyoshi Kaneko、Akio Maeda、Kohji Watanabe、Eiichi Fujita

  DOI：10.1016/s0040-4039(01)93013-8

  日期：1977.1