(3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-hydroxy-4H-1-benzopyran-4-one

• 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: (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-hydroxy-4H-1-benzopyran-4-one
• 英文别名: (E)-3-(4-(dimethylamino)benzylidene)-7-hydroxychroman-4-one
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: JEHAHVQWJZKUEI-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-hydroxy-4H-1-benzopyran-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88%的产率得到(E)-3-(4-(dimethylamino)benzylidene)-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 哌啶 、 sodium hydroxide 作用下， 反应 4.0h， 生成 (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-7-hydroxy-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

  摘要：

  合成了一系列 3-亚苄基-4-色满酮衍生物（3-20），并评估了其抗氧化和抑制α-葡萄糖苷酶活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 5、13 和 18 显示出了强效的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（5：EC50 13 µM；13：EC50 14 µM；18：EC50 13 µM）。化合物 12、14 和 18 显示出较高的α-葡萄糖苷酶抑制活性（12：IC50 15 µM；14：IC50 25 µM；18：IC50 28 µM）。化合物 18 同时显示了强效的 DPPH 自由基清除活性和 α-葡萄糖苷酶抑制活性。这些数据表明，3-亚苄基-4-色满酮衍生物（如化合物 18）可作为先导化合物，用于开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂。

  DOI：

  10.1248/cpb.c16-00327

文献信息

• Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
  作者：Vidavalur Siddaiah、Chunduri Venkata Rao、Somepalli Venkateswarlu、Alluri V. Krishnaraju、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2005.11.031

  日期：2006.4

  vitro for their inhibitory activities against 5-lipoxygenase (5-LOX) enzyme. The analog 7-hydroxy-3-[(N,N-dimethylaminophenyl)methylene]chroman-4-one was found to possess potent inhibitory activity and was comparable to that of the standard, nordihydroguiaretic acid. These results suggest that these homoisoflavonoids, with their potent antioxidant and 5-LOX inhibitory activities, may have useful applications

  在四个步骤中，从适当取代的苯酚到苯并吡喃-4-酮合成了一系列四种天然存在的异黄酮类化合物和八种类似物。根据NMR光谱数据将产物指定为E-异构体。通过光异构化将E-异构体转化为Z-异构体。E-和Z-异构体显示出明显的化学位移，质子NMR光谱中（E）和（Z）-均异类黄酮之间的差异为确定立体化学提供了一种有用的方法。通过超氧化物歧化酶（NBT）和DPPH自由基清除方法测定了异黄酮类化合物的抗氧化活性。类似物7-羟基-3-[（3,4，5-三羟基苯基）亚甲基] chroman-4-one在这两种方法中均表现出优异的活性，其次是沙酮A，并且其效力比市售抗氧化剂如BHA，BHT等高出数倍。对这些化合物的体外抑制活性进行了评估-脂氧合酶（5-LOX）酶。发现类似物7-羟基-3-[（N，N-二甲基氨基苯基）亚甲基]苯并吡喃-4-酮具有有效的抑制活性，并且与标准的去甲二氢癸二酸相当。这些结果表明，这些同型异黄
• 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.
• Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors
  作者：Koichi Takao、Marimo Yamashita、Aruki Yashiro、Yoshiaki Sugita

  DOI：10.1248/cpb.c16-00327

  日期：——

  A series of 3-benzylidene-4-chromanone derivatives (3–20) were synthesized and the structure–activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 µM; 13: EC50 14 µM; 18: EC50 13 µM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 µM; 14: IC50 25 µM; 18: IC50 28 µM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

  合成了一系列 3-亚苄基-4-色满酮衍生物（3-20），并评估了其抗氧化和抑制α-葡萄糖苷酶活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 5、13 和 18 显示出了强效的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（5：EC50 13 µM；13：EC50 14 µM；18：EC50 13 µM）。化合物 12、14 和 18 显示出较高的α-葡萄糖苷酶抑制活性（12：IC50 15 µM；14：IC50 25 µM；18：IC50 28 µM）。化合物 18 同时显示了强效的 DPPH 自由基清除活性和 α-葡萄糖苷酶抑制活性。这些数据表明，3-亚苄基-4-色满酮衍生物（如化合物 18）可作为先导化合物，用于开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂。