(E)-1-(phenanthren-2-yl)-3-phenylprop-2-en-1-one | 5756-23-0

• 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
• 英文名称: (E)-1-(phenanthren-2-yl)-3-phenylprop-2-en-1-one
• 英文别名: 3-Oxo-3-phenanthryl-(2)-1-phenyl-propen-(1)；<2>Phenanthryl-trans-styryl-keton；1-[2]phenanthryl-3t-phenyl-propenone；1-[2]Phenanthryl-3t-phenyl-propenon；1-(2-phenanthrenyl)-3-phenylprop-2-en-1-one；1-(2-Phenanthryl)-3-phenylprop-2-en-1-one；(E)-1-phenanthren-2-yl-3-phenylprop-2-en-1-one
• CAS: 5756-23-0
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: LUJIHZCAANPPOD-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• 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：

  (E)-1-(phenanthren-2-yl)-3-phenylprop-2-en-1-one 在 magnesium oxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 2-[3-oxo-3-(2-phenanthrenyl)-1-phenylpropyl]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：

  2-乙酰基菲 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (E)-1-(phenanthren-2-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  通过反电子需量Diels–Alder反应 合成对称和不对称的三芳基py离子†

  摘要：

  据报道，BF 3 ·OEt 2介导的查耳酮与芳基乙炔的逆电子需求Diels-Alder（IEDDA）反应可合成对称和不对称的2,4,6-三芳基aryl离子。该协议为在温和的反应条件下利用容易获得的简单底物提供了一种有效的一锅法，从而以适度的好收率产生了一系列的吡啶离子。

  DOI：

  10.1039/c8cc06444j

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。
• Synthesis of 1-substituted 3,5-diaryl-2-pyrazolines by the reaction of α,β-unsaturated ketones with hydrazines
  作者：Albert Lévai、József Jekö

  DOI：10.1002/jhet.5570430117

  日期：2006.1

  1-Acetyl-, 1-propionyl- and 1-phenyl-3,5-diaryl-2-pyrazolines have been synthesized by the reaction of the appropriate α,β-unsaturated ketones with hydrazine or phenylhydrazine in hot acetic acid or propionic acid. Structures of all new 2-pyrazolines 16-40 have been elucidated by microanalyses, 1H and 13C nmr spectroscopies.

  通过适当的α，β-不饱和酮与肼或苯肼在热乙酸或丙酸中的反应，已经合成了1-乙酰基，1-丙酰基-和1-苯基-3，5-二芳基-2-吡唑啉。所有新的2-吡唑啉16-40的结构已通过微量分析，1 H和13 C nmr光谱学得以阐明。
• Allosteric protein kinase modulators
  申请人：Universität des Saarlandes

  公开号：EP2177510A1

  公开（公告）日：2010-04-21

  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.

  本发明提供了可异位调节 AGC 蛋白激酶和 Aurora 家族蛋白激酶活性或调节蛋白-蛋白相互作用的特异性小分子化合物、其生产方法、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性相关疾病的药物的用途。
• 1246. The reversible prototropic isomerisation of 1,3-arylphenyl-propenes. The relative conjugating power of aryl substituents
  作者：D. R. Ross、E. S. Waight

  DOI：10.1039/jr9650006710

  日期：——