2-(benzylthio)-1-(4-bromophenyl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(benzylthio)-1-(4-bromophenyl)ethan-1-one
• 英文别名: 2-(benzylthio)-1-(4-bromophenyl)ethanone；2-(Benzylsulfanyl)-1-(4-bromophenyl)ethanone；2-benzylsulfanyl-1-(4-bromophenyl)ethanone
• 化学式: C₁₅H₁₃BrOS
• mdl: MFCD01603685
• 分子量: 321.238
• InChiKey: FEZWFPZMWMYFSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  2-(benzylthio)-1-(4-bromophenyl)ethan-1-one 在 ammonium acetate 、 双氧水 、 溶剂黄146 作用下， 反应 1.0h， 生成 (E)-2-benzylsulfonyl-1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors

  摘要：

  Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-alpha-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 mu M for BRAF(V600E) and GI(50) value of 0.52 mu M for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.007
• 作为产物：
  描述：

  4-溴苯乙酮 在 溴 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 2-(benzylthio)-1-(4-bromophenyl)ethan-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors

  摘要：

  Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-alpha-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 mu M for BRAF(V600E) and GI(50) value of 0.52 mu M for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.007

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。
• Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds
  作者：Taigang Zhou、Byron Peters、Matías F. Maldonado、Thavendran Govender、Pher G. Andersson

  DOI：10.1021/ja306731u

  日期：2012.8.22

  A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up

  开发了一种高效且对映选择性 Ir 催化的不饱和砜加氢反应。以优异的对映选择性（高达 98% ee）生产手性环状和无环砜。与 Ramberg-Bäcklund 重排相结合，该反应提供了一种获得具有优异对映选择性（高达 97% ee）和高产率（高达 94%）的手性烯丙基和同型烯丙基化合物的新途径。
• Stevens rearrangement of thioethers with arynes: a facile access to multi-substituted β-keto thioethers
  作者：Xiao-Bo Xu、Zi-Hua Lin、Yuyin Liu、Jian Guo、Yun He

  DOI：10.1039/c7ob00277g

  日期：——

  An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C–S/C–H/C–C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.

  已经开发了一种通过简单的β-酮硫醚与芳烃的史蒂文斯重排合成多取代的β-酮硫醚的有效方法。在这些反应中，在温和无过渡金属条件下，在一个锅中形成连续的C–S / C–H / C–C键，以中等至良好的产率提供多取代的β-酮硫醚。
• 一种多取代β-酮硫醚的制备方法
  申请人：重庆大学

  公开号：CN107200700A

  公开（公告）日：2017-09-26

  本发明涉及多取代β‑酮硫醚类化合物的制备方法，以芳炔化合物、硫醚化合物和氟化物作为反应试剂组合物，在温和的反应条件下制备一系列含多取代β‑酮硫醚骨架结构的化合物。本发明反应所用试剂易于制备、价格低廉、后处理简单，具有很高的原子经济性。本发明为制备该系列化合物提供了一种简洁、高效、价格低廉、选择性高并适于产业化的技术手段。
• Indium-mediated Reaction in Aqueous Media. Synthesis of Phenacyl Sulfides by Reactions of α-Bromoketones with Sodium Alkyl Thiosulfates†
  作者：Zhuangping Zhan、Yongmin Zhang、Zhenghai Ma

  DOI：10.1039/a705031c

  日期：——

  Phenacyl sulfides are synthesized in moderate to good yields via reaction of α-haloketones with sodium alkyl thiosulfates promoted by indium metal in aqueous media.

  通过 α-卤代酮与烷基硫代硫酸钠在水性介质中受铟金属促进的反应，以中等至良好的收率合成苯酰硫醚。