3-[3-(1,3-benzodioxol-5-yl)propyl]phenol | 1312836-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-[3-(1,3-benzodioxol-5-yl)propyl]phenol
• CAS: 1312836-14-8
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: RJJKWQFMUVTPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one 在 硫酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、413.69 kPa 条件下， 反应 4.0h， 以58%的产率得到3-[3-(1,3-benzodioxol-5-yl)propyl]phenol
  参考文献：
  名称：

  Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors

  摘要：

  Several analogs of gigantol (1) were synthesized to evaluate their effect on the complexes Ca(2+)-calmodulin (CaM) and Ca(2+)-CaM-CaM sensitive phosphodiesterase 1 (PDE1). The compounds belong to four structural groups including, 1,2-diphenylethanes (2-11), diphenylmethanes (13-15), 1,3-diphenylpropenones (16-18), and 1,3-diphenylpropanes (20-22). In vitro enzymatic studies showed that all compounds except 11 inhibited the complex Ca(2+)-CaM-PDE1 with IC(50) values ranging from 9 to 146 mu M. On the other hand, all analogs but 11,12 and 15 quenched the extrinsic fluorescence of the CaM biosensor hCaM-M124C-mBBr to different extent, then revealing different affinities to CaM; their affinity constants (K(m)) values were in the range of 3-80 mu M. Molecular modeling studies indicated that all these compounds bound to CaM at the same site that the classical inhibitors trifluoperazine (TFP) and chlorpromazine (CPZ). Some of these analogs could be worthy candidates for developing new anti-tumor, local anesthetics, antidepressants, antipsychotic, or smooth muscle relaxant drugs, with anti-CaM properties due to their good affinity to CaM and the straightforwardness of their synthesis. In addition they could be valuable tools for the study of Ca(2+)-CaM functions. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.057

文献信息

• Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors
  作者：Adelfo Reyes-Ramírez、Martha Leyte-Lugo、Mario Figueroa、Trinidad Serrano-Alba、Martín González-Andrade、Rachel Mata

  DOI：10.1016/j.ejmech.2011.03.057

  日期：2011.7

  Several analogs of gigantol (1) were synthesized to evaluate their effect on the complexes Ca(2+)-calmodulin (CaM) and Ca(2+)-CaM-CaM sensitive phosphodiesterase 1 (PDE1). The compounds belong to four structural groups including, 1,2-diphenylethanes (2-11), diphenylmethanes (13-15), 1,3-diphenylpropenones (16-18), and 1,3-diphenylpropanes (20-22). In vitro enzymatic studies showed that all compounds except 11 inhibited the complex Ca(2+)-CaM-PDE1 with IC(50) values ranging from 9 to 146 mu M. On the other hand, all analogs but 11,12 and 15 quenched the extrinsic fluorescence of the CaM biosensor hCaM-M124C-mBBr to different extent, then revealing different affinities to CaM; their affinity constants (K(m)) values were in the range of 3-80 mu M. Molecular modeling studies indicated that all these compounds bound to CaM at the same site that the classical inhibitors trifluoperazine (TFP) and chlorpromazine (CPZ). Some of these analogs could be worthy candidates for developing new anti-tumor, local anesthetics, antidepressants, antipsychotic, or smooth muscle relaxant drugs, with anti-CaM properties due to their good affinity to CaM and the straightforwardness of their synthesis. In addition they could be valuable tools for the study of Ca(2+)-CaM functions. (C) 2011 Elsevier Masson SAS. All rights reserved.