(E)-3-(4-(3-morpholinopropoxy)benzylidene)-2,3-dihydro-7-ethoxychromen-4-one hydrochloride

• 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: (E)-3-(4-(3-morpholinopropoxy)benzylidene)-2,3-dihydro-7-ethoxychromen-4-one hydrochloride
• 英文别名: (3E)-7-ethoxy-3-[[4-(3-morpholin-4-ylpropoxy)phenyl]methylidene]chromen-4-one;hydrochloride
• 化学式: C₂₅H₂₉NO₅*ClH
• 分子量: 459.97
• InChiKey: BQLDQKGIERTOTP-QTNJPTFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(3-氯丙氧基)苯甲醛 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.08h， 生成 (E)-3-(4-(3-morpholinopropoxy)benzylidene)-2,3-dihydro-7-ethoxychromen-4-one hydrochloride
  参考文献：
  名称：

  Design, synthesis and anticholinesterase activity of novel benzylidenechroman-4-ones bearing cyclic amine side chain

  摘要：

  A series of 3-(4-(aminoalkoxy)benzylidene)-chroman-4-ones 7a-r were designed and synthesized as analogs of homoisoflavonoids which are well known natural products with diverse pharmacological properties related to Alzheimer's disease. The in vitro anti-cholinesterase activity of designed compounds 7a-r against AChE and BuChE, revealed that compounds bearing piperidinylethoxy residue showed potent activity against AChE at sub-micromolar level (IC50 values = 0.122-0.207 mu M), more potent than reference drug tacrine. The structure-activity relationships study of piperidinylethoxy series demonstrated that the selectivity and physicochemical properties of compounds could be optimized by selection of a proper substituent on the C-7 position of chroman ring, while the high potency of the molecule against AChE was reserved. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.055

文献信息

• Design, synthesis and anticholinesterase activity of novel benzylidenechroman-4-ones bearing cyclic amine side chain
  作者：Yaghoub Pourshojaei、Ali Gouranourimi、Shohre Hekmat、Ali Asadipour、Samira Rahmani-Nezhad、Alireza Moradi、Hamid Nadri、Farshad Homayouni Moghadam、Saeed Emami、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2015.04.055

  日期：2015.6

  A series of 3-(4-(aminoalkoxy)benzylidene)-chroman-4-ones 7a-r were designed and synthesized as analogs of homoisoflavonoids which are well known natural products with diverse pharmacological properties related to Alzheimer's disease. The in vitro anti-cholinesterase activity of designed compounds 7a-r against AChE and BuChE, revealed that compounds bearing piperidinylethoxy residue showed potent activity against AChE at sub-micromolar level (IC50 values = 0.122-0.207 mu M), more potent than reference drug tacrine. The structure-activity relationships study of piperidinylethoxy series demonstrated that the selectivity and physicochemical properties of compounds could be optimized by selection of a proper substituent on the C-7 position of chroman ring, while the high potency of the molecule against AChE was reserved. (C) 2015 Elsevier Masson SAS. All rights reserved.