2,3-二氢-7-羟基-3-[(4-甲氧基苯基)甲基]-4H-1-苯并吡喃-4-酮 | 103680-87-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 中文名称: 2,3-二氢-7-羟基-3-[(4-甲氧基苯基)甲基]-4H-1-苯并吡喃-4-酮
• 英文名称: 3-(4-methoxy)-benzyl-7-hydroxy-4-chromanone
• 英文别名: 7-hydroxy-3-(4-methoxybenzyl)chroman-4-one；7-hydroxy-4'-methoxyhomoisoflavanone；dihydrobonducellin；7-hydroxy-3-[(4-methoxyphenyl)methyl]-2,3-dihydrochromen-4-one
• CAS: 103680-87-1
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: UCRZVWKJRYPHMU-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  495.0±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二氢-7-羟基-3-[(4-甲氧基苯基)甲基]-4H-1-苯并吡喃-4-酮 、 N-(6-bromohexyl)-1,2,3,4-tetrahydroacridin-9-amine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以66%的产率得到3-(4-methoxybenzyl)-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：

  (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium carbonate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 6.0h， 生成 2,3-二氢-7-羟基-3-[(4-甲氧基苯基)甲基]-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  A new synthesis of homoisoflavanones (3-benzyl-4-chromanones)

  摘要：

  DOI：

  10.1016/s0040-4020(01)91433-4

文献信息

• Jain, A. C.; Mehta, Anita, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1170 - 1171
  作者：Jain, A. C.、Mehta, Anita

  DOI：——

  日期：——
• 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.
• A new synthesis of homoisoflavanones (3-benzyl-4-chromanones)
  作者：Amolak C. Jain、(Mrs) Anita Mehta (Nèe Anita Sharma)

  DOI：10.1016/s0040-4020(01)91433-4

  日期：1985.1