7-hydroxy-(E)-3-[(4-fluorophenyl)methylene]chroman-4-one | 1449232-60-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 7-hydroxy-(E)-3-[(4-fluorophenyl)methylene]chroman-4-one
• 英文别名: (E)-3-(4-fluorobenzylidene)-7-hydroxychroman-4-one；(3E)-3-[(4-fluorophenyl)methylene]-7-hydroxy-chroman-4-one；(3E)-3-[(4-fluorophenyl)methylidene]-7-hydroxychromen-4-one
• CAS: 1449232-60-3
• 化学式: C₁₆H₁₁FO₃
• 分子量: 270.26
• InChiKey: BCWCHRYXGNUZLX-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-(E)-3-[(4-fluorophenyl)methylene]chroman-4-one 、 N-(5-bromopentyl)-1,2,3,4-tetrahydroacridin-9-amine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以36%的产率得到(E)-3-(4-fluorobenzylidene)-7-(6-(1,2,3,4-tetrahydroacridin-9-ylamino)hexyloxy)chroman-4-one
  参考文献：
  名称：

  Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine–Homoisoflavonoid hybrids

  摘要：

  A series of Tacrine-Homoisoflavonoid hybrids were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and human monoamine oxidases (MAOs). Most of the compounds were found to be potent against both ChEs and MAO-B. Among these hybrids, compound 8b, with a 6 carbon linker between tacrine and (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one, proved to be the most potent against AChE and MAO-B with IC50 values of 67.9 nM and 0.401 mu M, respectively. This compound was observed to cross the blood-brain barrier (BBB) in a parallel artificial membrane permeation assay for the BBB (PAMPA-BBB). The results indicated that compound 8b is an excellent multifunctional promising compound for development of novel drugs for Alzheimer's disease (AD). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.050
• 作为产物：
  描述：

  3-氯-1-(2,4-二羟基苯基)丙烷-1-酮 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 26.41h， 生成 7-hydroxy-(E)-3-[(4-fluorophenyl)methylene]chroman-4-one
  参考文献：
  名称：

  7-羟基-（E）-3-苯基亚甲基-chroman-4-one类似物作为耻垢分枝杆菌mc 2 155的外排泵抑制剂

  摘要：

  外排泵（EP）在分枝杆菌中诱导耐药性，因此可以作为发现抗结核病药物的新靶标进行探索。为了从天然产物邦杜菌素中寻找外排泵抑制剂，从洋地黄（Caesalpinia digyna）根中分离了同异黄酮，并对其调制和EP抑制活性进行了评估。Bonducellin在62.5 mg / L的浓度下对EtBr的MIC表现出八倍的调节，并且还表现出显着的EP抑制活性。设计合成方案以通过在苯基亚甲基环上进行修饰来制备7-羟基-（E）-3-苯基亚甲基-苯并二氢吡喃-4-酮的类似物，并在累积和流出试验中评估合成的化合物。类似物1，7 - 11，13 - 15，17和19被认为是良好的调制器和由≥4倍在亚抑制浓度降低的EtBr的MIC。化合物8，13和17是最有效的抑制剂溴化乙锭流出在耻垢分枝杆菌MC 2 155。

  DOI：

  10.1016/j.ejmech.2013.06.024

文献信息

• Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine–Homoisoflavonoid hybrids
  作者：Yang Sun、Jianwen Chen、Xuemin Chen、Ling Huang、Xingshu Li

  DOI：10.1016/j.bmc.2013.09.050

  日期：2013.12

  A series of Tacrine-Homoisoflavonoid hybrids were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and human monoamine oxidases (MAOs). Most of the compounds were found to be potent against both ChEs and MAO-B. Among these hybrids, compound 8b, with a 6 carbon linker between tacrine and (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one, proved to be the most potent against AChE and MAO-B with IC50 values of 67.9 nM and 0.401 mu M, respectively. This compound was observed to cross the blood-brain barrier (BBB) in a parallel artificial membrane permeation assay for the BBB (PAMPA-BBB). The results indicated that compound 8b is an excellent multifunctional promising compound for development of novel drugs for Alzheimer's disease (AD). (C) 2013 Elsevier Ltd. All rights reserved.
• 7-Hydroxy-(E)-3-phenylmethylene-chroman-4-one analogues as efflux pump inhibitors against Mycobacterium smegmatis mc2 155
  作者：Somendu K. Roy、Neela Kumari、Shiv Gupta、Sonika Pahwa、Hemraj Nandanwar、Sanjay M. Jachak

  DOI：10.1016/j.ejmech.2013.06.024

  日期：2013.8

  Efflux pump (EP) induces resistance in mycobacteria and hence could be explored as a new target for the discovery of anti-TB agents. In search for efflux pump inhibitors from natural products, bonducellin, a homoisoflavonoid was isolated from Caesalpinia digyna roots and evaluated for modulation and EP inhibitory activity. Bonducellin showed modulation in the MIC of EtBr by eight fold at a concentration

  外排泵（EP）在分枝杆菌中诱导耐药性，因此可以作为发现抗结核病药物的新靶标进行探索。为了从天然产物邦杜菌素中寻找外排泵抑制剂，从洋地黄（Caesalpinia digyna）根中分离了同异黄酮，并对其调制和EP抑制活性进行了评估。Bonducellin在62.5 mg / L的浓度下对EtBr的MIC表现出八倍的调节，并且还表现出显着的EP抑制活性。设计合成方案以通过在苯基亚甲基环上进行修饰来制备7-羟基-（E）-3-苯基亚甲基-苯并二氢吡喃-4-酮的类似物，并在累积和流出试验中评估合成的化合物。类似物1，7 - 11，13 - 15，17和19被认为是良好的调制器和由≥4倍在亚抑制浓度降低的EtBr的MIC。化合物8，13和17是最有效的抑制剂溴化乙锭流出在耻垢分枝杆菌MC 2 155。