2-(4-methoxyphenyl)-3-(4-nitrobenzoyl)benzofuran | 1449687-95-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-methoxyphenyl)-3-(4-nitrobenzoyl)benzofuran
• 英文别名: (2-(4-methoxyphenyl)benzofuran-3-yl)(4-nitrophenyl)methanone；[2-(4-Methoxyphenyl)benzofuran-3-yl]-(4-nitrophenyl)methanone；[2-(4-methoxyphenyl)-1-benzofuran-3-yl]-(4-nitrophenyl)methanone
• CAS: 1449687-95-9
• 化学式: C₂₂H₁₅NO₅
• 分子量: 373.365
• InChiKey: NNVGMRQPYRCFCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-3-(4-nitrobenzoyl)benzofuran 在 potassium carbonate 、 potassium iodide 、 tin(ll) chloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.17h， 生成 (4-(bis(4-fluorobenzyl)amino)phenyl)(2-(4-methoxyphenyl)benzofuran-3-yl)methanone
  参考文献：
  名称：

  Discovery of novel benzofuran-based compounds with neuroprotective and immunomodulatory properties for Alzheimer's disease treatment

  摘要：

  To address the multifactorial nature of Alzheimer's Disease (AD), a multi-target-directed ligand approach was herein developed. As a follow-up of our previous studies, a small library of newly designed 2-arylbenzofuran derivatives was evaluated towards cholinesterases and cannabinoid receptors. The two most promising compounds, 8 and 10, were then assessed for their neuroprotective activity and for their ability to modulate the microglial phenotype. Compound 8 emerged as able to fight AD from several directions: it restored the cholinergic system by inhibiting butyrylcholinesterase, showed neuroprotective activity against A beta(1-42) oligomers, was a potent and selective CB2 ligand and had immunomodulatory effects, switching microglia from the pro-inflammatory M1 to the neuroprotective M2 phenotype. Derivative 10 was a potent CB2 inverse agonist with promising immunomodulatory properties and could be considered as a tool for investigating the role of CB2 receptors and for developing potential immunomodulating drugs addressing the endocannabinoid system. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.080
• 作为产物：
  描述：

  1-methoxy-2-((4-methoxyphenyl)ethynyl)benzene 在 四氯化锡 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(4-methoxyphenyl)-3-(4-nitrobenzoyl)benzofuran
  参考文献：
  名称：

  Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth

  摘要：

  A series of polysubstituted benzofuran derivatives was easily and rapidly prepared using a tandem Sonogashira coupling/cyclization reaction. Subsequent acylation afforded a small library of 39 new compounds that were assayed in cellulo on Plasmodium falciparum and Tiypanosoma brucei parasites. Some of them exhibited good inhibitory activity on T. brucei proliferation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.002

文献信息

• GC/MS ^<i>n</i> analysis of the crude reaction mixtures from Friedel–Crafts acylation: Unambiguous identification and differentiation of 3‐aroylbenzofurans from their 4‐ and 6‐regioisomers
  作者：Michela Begala、Michele Mancinelli、Elias Quezada、Giovanna Lucia Delogu

  DOI：10.1002/rcm.9082

  日期：2021.6.15

  and their 2‐nitrophenyl derivatives constitute fundamental intermediates for the synthesis of target compounds with pharmaceutical properties. However, their preparation by the Friedel‐Crafts acylation of 2‐phenylbenzofurans, using Lewis acid as catalyst, often leads to mixtures of regioisomeric aroylbenzofurans that can be challenging to distinguish, thus preventing the reaction characterization.

  3-芳基苯并呋喃及其2-硝基苯基衍生物构成合成具有药物特性的目标化合物的基本中间体。但是，使用路易斯酸作为催化剂，通过2-苯基苯并呋喃的Friedel-Crafts酰化反应制备的方法通常会导致难以区分的区域异构芳基苯并呋喃的混合物，从而阻碍了反应的表征。
• Regioselective synthesis of new EWG-Bearing 3-benzoyl-2-phenylbenzofurans by one-pot intramolecular acylation/thermal cyclization of phosphoranes and their CB1 antagonist activity
  作者：Michela Begala、Michele Mancinelli、Rafaela Mostallino、Maria Paola Castelli、Giovanna Lucia Delogu

  DOI：10.1016/j.tet.2024.133880

  日期：2024.3

  improved regioselective synthetic strategy, tandem ylide acylation and thermal cyclization of the acyl ylide intermediate. Using our optimized method, only one 3-acyl regioisomer was obtained and the yields were highly improved (up to 92 %) comparing to the previously reported method, expanding the scope of synthesis to a wide variety of new EWG-containing 3-benzoyl-2-phenylbenzofurans. The synthesized

  (苯甲酰亚甲基)三苯基正膦是合成3-苯甲酰基-2-苯基苯并呋喃的有用中间体。在 Wittig 条件下，它们可以同时制备两种 3-酰基区域异构体。从邻苯甲酰氧基环（硝基、氰基和三氟甲基）上带有吸电子基团（EWG）的-[（苯甲酰氧基）亚苄基]三苯基鏻盐开始，我们开发了一种改进的区域选择性合成策略，串联叶立德酰化和热环化酰基叶立德中间体。使用我们的优化方法，仅获得了一种 3-酰基区域异构体，与之前报道的方法相比，产率大幅提高（高达 92%），将合成范围扩大到多种新型的含 EWG 的 3-苯甲酰基- 2-苯基苯并呋喃。评估了合成化合物对 CB1 受体的活性。特别是，其中一些化合物显示出作为 CB1 拮抗剂的活性。
• Discovery of novel benzofuran-based compounds with neuroprotective and immunomodulatory properties for Alzheimer's disease treatment
  作者：Serena Montanari、Ali Mokhtar Mahmoud、Letizia Pruccoli、Alessandro Rabbito、Marina Naldi、Sabrina Petralla、Ignacio Moraleda、Manuela Bartolini、Barbara Monti、Isabel Iriepa、Federica Belluti、Silvia Gobbi、Vincenzo Di Marzo、Alessandra Bisi、Andrea Tarozzi、Alessia Ligresti、Angela Rampa

  DOI：10.1016/j.ejmech.2019.05.080

  日期：2019.9

  To address the multifactorial nature of Alzheimer's Disease (AD), a multi-target-directed ligand approach was herein developed. As a follow-up of our previous studies, a small library of newly designed 2-arylbenzofuran derivatives was evaluated towards cholinesterases and cannabinoid receptors. The two most promising compounds, 8 and 10, were then assessed for their neuroprotective activity and for their ability to modulate the microglial phenotype. Compound 8 emerged as able to fight AD from several directions: it restored the cholinergic system by inhibiting butyrylcholinesterase, showed neuroprotective activity against A beta(1-42) oligomers, was a potent and selective CB2 ligand and had immunomodulatory effects, switching microglia from the pro-inflammatory M1 to the neuroprotective M2 phenotype. Derivative 10 was a potent CB2 inverse agonist with promising immunomodulatory properties and could be considered as a tool for investigating the role of CB2 receptors and for developing potential immunomodulating drugs addressing the endocannabinoid system. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth
  作者：Marion Thévenin、Sylviane Thoret、Philippe Grellier、Joëlle Dubois

  DOI：10.1016/j.bmc.2013.07.002

  日期：2013.9

  A series of polysubstituted benzofuran derivatives was easily and rapidly prepared using a tandem Sonogashira coupling/cyclization reaction. Subsequent acylation afforded a small library of 39 new compounds that were assayed in cellulo on Plasmodium falciparum and Tiypanosoma brucei parasites. Some of them exhibited good inhibitory activity on T. brucei proliferation. (C) 2013 Elsevier Ltd. All rights reserved.