1-(4-溴苯基)-3-(4-氯苯基)丙-2-烯-1-酮 | 126443-16-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(4-溴苯基)-3-(4-氯苯基)丙-2-烯-1-酮
• 英文名称: (E)-1-(4-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• 英文别名: ACETOPHENONE, 4'-BROMO-2-(p-CHLOROBENZYLIDENE)-
• CAS: 126443-16-1
• 化学式: C₁₅H₁₀BrClO
• 分子量: 321.601
• InChiKey: HYCQSDMDGCPEPI-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-溴苯基)-3-(4-氯苯基)丙-2-烯-1-酮 在 sodium hydride 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 2-(3-(4-bromophenyl)-1-(4-chlorophenyl)-3-oxopropyl)malonic acid
  参考文献：
  名称：

  2-(3-Oxo-1,3-diphenylpropyl)malonic Acids as Potent Allosteric Ligands of the PIF Pocket of Phosphoinositide-Dependent Kinase-1: Development and Prodrug Concept

  摘要：

  The protein kinase C-related kinase 2 (PRK2)interacting fragment (PIF) pocket of phosphoinositide-dependent kinase-1 (PDK1) was proposed as a novel target site for allosteric modulators. In the present work, We describe the design, synthesis, and structure-activity relationship of a series of 2-(3-oxo-1,3- diphenylprapyl)malonic acids as potent allosteric activators binding, to the PIF pocket: Some congeners displayed AC(50) values for PDK1 activation in the submicromolar range. The potency of the best compounds to stabilize PDK1 in a thermal stability shift assay was in the same order Of magnitude as that of the PIF pocket binding peptide PIFtide, suggesting comparable binding affinities to the pm pocket, The crystal structure of PDK1 in complex with compound 4h revealed that additional ionic interactions are mainly responsible for the increased potency compared to the monocarboxylate analogues. Notably, several compounds displayed high selectivity for PDK1 Employing a prodrug strategy, we were able to corrroborate the novel mechanism of action in cells.

  DOI：

  10.1021/jm3010477
• 作为产物：
  描述：

  在 叔丁基过氧化氢 、 四丁基溴化铵 作用下， 以 癸烷 、 苯 为溶剂， 反应 24.0h， 以88%的产率得到1-(4-溴苯基)-3-(4-氯苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  四正丁基溴化铵：温和条件下酒精氧化的一种简单而有效的有机催化剂

  摘要：

  首次鉴定出一种简单而有效的有机催化体系，该体系以5 mol％的四正丁基溴化铵（TBAB）为催化剂。该有机催化体系可与多种具有各种催化反应性基团的苄基/烯丙基醇相容。此外，它对仲苄醇的选择性优于脂族醇，对4-（1-羟乙基）苄醇的伯苄醇位具有良好的选择性。因此，与该TBAB有机催化体系相关的反应条件的简单，高效，选择性和温和的特征表明其在合成化学中的广泛应用的潜力。

  DOI：

  10.1002/adsc.201400100

文献信息

• [EN] ALLOSTERIC PROTEIN KINASE MODULATORS<br/>[FR] MODULATEURS DE PROTÉINE KINASE ALLOSTÉRIQUE
  申请人：UNIV SAARLAND

  公开号：WO2010043711A1

  公开（公告）日：2010-04-22

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  该发明提供特定的小分子化合物，这些化合物能够变构调节AGC蛋白激酶的活性或调节Aurora家族蛋白激酶的蛋白-蛋白相互作用，提供这些化合物的制备方法，包含这些化合物的药物组合物，以及它们用于制备治疗和预防与AGC蛋白激酶或Aurora家族蛋白激酶异常活动相关疾病的药物的应用。
• ALLOSTERIC PROTEIN KINASE MODULATORS
  申请人：Engel Matthias

  公开号：US20120046307A1

  公开（公告）日：2012-02-23

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  本发明提供了特定的小分子化合物，它们通过变构调节AGC蛋白激酶的活性或调节Aurora家族蛋白激酶的蛋白质-蛋白质相互作用，其生产方法，包含该化合物的药物组合物，以及它们用于制备治疗和预防与AGC蛋白激酶或Aurora家族蛋白激酶异常活动相关疾病的药物的应用。
• Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles
  作者：Vidya G. Desai、Pooja C. Satardekar、Sampada Polo、Kashinath Dhumaskar

  DOI：10.1080/00397911.2010.531492

  日期：2012.3.15

  Abstract A new and a simple approach toward synthesis of 1,3,5-trisubstituted pyrazoles from chalcone arylhydrazones via oxidative cyclization has been achieved. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone was successfully used as an oxidizing agent to give excellent yields of pyrazoles. GRAPHICAL ABSTRACT

  摘要 已经实现了一种通过氧化环化从查耳酮芳基腙合成 1,3,5-三取代吡唑的新方法和简单方法。2,3-二氯-5,6-二氰基-1,4-苯醌被成功用作氧化剂，得到了极好的吡唑收率。图形概要
• Michael-Michael Ring Closure Reaction of Benzyl Cyanides and Chalcones
  作者：Mohammad M. Al-Arab、Bader S. Ghanem、Marilyn M. Olmstead

  DOI：10.1055/s-1992-26289

  日期：——

  The synthesis of a number of highly substituted cyclohexane derivatives has been accomplished in a single step reaction of benzyl cyanides and chalcones (1:2) using sodium ethoxide in anhydrous diethyl ether at room temperature to give 3-aroyl-1,2,4, 6-tetraaryl-4-hydroxycyclohexanecarbonitriles. An unambiguous structural assignment was achieved from the analytical and infrared, 1H NMR and 13C NMR spectroscopic data as well as X-ray crystallography.

  已经通过在室温下使用无水乙醚中的乙醇钠，将苄基氰和烯酮（1:2）进行一步反应，成功合成了一系列高度取代的环己烷衍生物，生成了3-芳酰-1,2,4,6-四芳基-4-羟基环己烷碳腈。通过分析数据、红外光谱、1H NMR和13C NMR光谱数据以及X射线晶体学，实现了明确的结构归属。
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。

表征谱图