3-(3,4,5-Trimethoxy-phenylethynyl)-phenol | 1042149-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3,4,5-Trimethoxy-phenylethynyl)-phenol
• 英文别名: 3-[2-(3,4,5-trimethoxyphenyl)ethynyl]phenol
• CAS: 1042149-62-1
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: YXSIUUNNFKWPGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-Trimethoxy-phenylethynyl)-phenol 在 potassium permanganate 、 sodium carbonate 、 magnesium sulfate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design and synthesis of cyclic acylguanidines as BACE1 inhibitors

  摘要：

  Based on the lead compound 1 reported in literature, a series of novel BACE1 inhibitors were designed and synthesized, among which compound 11 exhibited a 14-fold improvement in potency over the lead compound 1. This represents a good lead for the discovery of more promising BACE1 inhibitors for the potential treatment of AD. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.020
• 作为产物：
  描述：

  3-碘苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 生成 3-(3,4,5-Trimethoxy-phenylethynyl)-phenol
  参考文献：
  名称：

  Design and synthesis of cyclic acylguanidines as BACE1 inhibitors

  摘要：

  Based on the lead compound 1 reported in literature, a series of novel BACE1 inhibitors were designed and synthesized, among which compound 11 exhibited a 14-fold improvement in potency over the lead compound 1. This represents a good lead for the discovery of more promising BACE1 inhibitors for the potential treatment of AD. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.020

文献信息

• Synthesis and antitumor activity of benzils related to combretastatin A-4
  作者：Céline Mousset、Anne Giraud、Olivier Provot、Abdallah Hamze、Jérôme Bignon、Jian-Miao Liu、Sylviane Thoret、Joëlle Dubois、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.bmcl.2008.04.053

  日期：2008.6

  A series of benzil derivatives related to combretastatin A-4 (CA-4) have been synthesized by oxidation of diarylalkynes promoted by PdI2 in DMSO. Using this new protocol, 14 benzils were prepared in good to excellent yields and their biological activity has been delineated. Several benzils exhibited excellent antiproliferative activity: for example, 4j and 4k bearing the greatest resemblance to CA-4 and AVE-8062, respectively, were found to inhibit cell growth at the nanomolar level (20-50 nM) on four human tumor cell lines. Flow cytometric analysis indicates that these compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. A cell-based assay indicated that compounds 4j and 4k displayed a similar inhibition of tubulin assembly with an IC50 value similar to CA-4. These results clearly demonstrated that the Z-double bond of CA-4 can be replaced by a 1,2-diketone unit without significant loss of cytotoxicity and inhibition of tubulin assembly potency. (C) 2008 Elsevier Ltd. All rights reserved.