5-(benzofuran-2-yl)quinolin-8-ol | 849222-28-2

• 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: 5-(benzofuran-2-yl)quinolin-8-ol
• 英文别名: 5-(1-benzofuran-2-yl)-8-hydroxy-quinoline；5-(1-benzofuran-2-yl)quinolin-8-ol
• CAS: 849222-28-2
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: CRLIXXNKXQZKMN-UHFFFAOYSA-N

物化性质

• 沸点：
  446.9±35.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-8-methoxy-5-(2-(methoxymethoxy)styryl)quinoline 在 盐酸 、 碘 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 5-(benzofuran-2-yl)quinolin-8-ol
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget-Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer’s Disease

  摘要：

  A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and A beta aggregation as well as remarkable antioxidant effects and excellent blood brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 mu M), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced A beta aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with A beta(1-42) at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d center dot HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.

  DOI：

  10.1021/acs.jmedchem.5b01222

文献信息

• [EN] SUBSTITUTED HETEROARYL BENZOFURAN ACIDS<br/>[FR] ACIDES HETEROARYL BENZOFURANE SUBSTITUES
  申请人：WYETH CORP

  公开号：WO2005030760A1

  公开（公告）日：2005-04-07

  The present invention relates generally to substituted heteroaryl benzofuran acids and methods of using them (I); or a pharmaceutically acceptable salt or ester form therof wherein: R, R1, R2 and R3 are, independently, hydrogen, alkyl, cycloalkyl, alkanoyl, halo, hydroxy, aryl, perfluoroalkyl, alkoxy, amino, alkylamino, dialkylamino, or perfluoroalkoxy; R4 is hydrogen, alkyl, perfluoroalkyl, alkenyl, alkynyl, arylalkenyl, arylalkynyl, aryl,-C(=O)R5, -C(=S)R5, -CH2R5, OR -CH(OH)R5; R5 is hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, perfluoroalkyl, aryl, alkenyl, alkynyl, arylalkyl, arylalkenyl, arylalkynyl, alkylaryl, alkenylaryl, or alkynylaryl; R6 is hydrogen, alkyl, aryl, or arylalkyl; x1, x2, x3, x4, x5, x6, x7, and x8 are, independently, carbon or nitrogen, wherein at least one of x1-x8 is a nitrogen atom; n is an integer from 0-6; and A is COOH or an acid mimic or a pharmaceutically acceptable salt thereof.

  本发明涉及一般地替代杂环芳基苯并呋喃酸及其使用方法（I）；或其药用可接受的盐或酯形式，其中：R、R1、R2和R3独立地是氢、烷基、环烷基、烷酰基、卤素、羟基、芳基、全氟烷基、烷氧基、氨基、烷基氨基、二烷基氨基或全氟烷氧基；R4是氢、烷基、全氟烷基、烯基、炔基、芳基烯基、芳基炔基、芳基、-C（=O）R5、-C（=S）R5、-CH2R5、OR或-CH（OH）R5；R5是氢、C1-C8烷基、C3-C8环烷基、全氟烷基、芳基、烯基、炔基、芳基烷基、芳基烯基、芳基炔基、烷基芳基、烯基芳基或炔基芳基；R6是氢、烷基、芳基或芳基烷基；x1、x2、x3、x4、x5、x6、x7和x8独立地是碳或氮，其中至少一个是氮原子；n是0-6之间的整数；A是COOH或酸模拟物或其药用可接受的盐。
• Substituted heteroaryl benzofuran acids
  申请人：Elokdah Mahmoud Hassan

  公开号：US20050119296A1

  公开（公告）日：2005-06-02

  The present invention relates generally to substituted heteroaryl benzofuran acids and methods of using them.

  本发明涉及替代杂环芳基苯并呋喃酸及其使用方法。
• SUBSTITUTED HETEROARYL BENZOFURAN ACIDS
  申请人：ELOKDAH Hassan Mahmoud

  公开号：US20090054484A1

  公开（公告）日：2009-02-26

  The present invention relates generally to substituted heteroaryl benzofuran acids and methods of using them.

  本发明通常涉及替代杂环芳基苯并呋喃酸及其使用方法。
• FUSED CYCLIC MODULATORS OF NUCLEAR HORMONE RECEPTOR FUNCTION
  申请人：Bristol-Myers Squibb Company

  公开号：EP1463728B1

  公开（公告）日：2009-01-14
• US7446201B2
  申请人：——

  公开号：US7446201B2

  公开（公告）日：2008-11-04