ethyl 5,6-dimethoxy-1-oxo-2-(prop-2-ynyl)-2,3-dihydro-1H-indene-2-carboxylate | 1465900-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl 5,6-dimethoxy-1-oxo-2-(prop-2-ynyl)-2,3-dihydro-1H-indene-2-carboxylate
• 英文别名: ethyl 5,6-dimethoxy-3-oxo-2-prop-2-ynyl-1H-indene-2-carboxylate
• CAS: 1465900-92-8
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: UFHJPXNWVZWNJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5,6-dimethoxy-1-oxo-2-(prop-2-ynyl)-2,3-dihydro-1H-indene-2-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以80%的产率得到5,6-dimethoxy-2-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Synthesis of indole based novel small molecules and their in vitro anti-proliferative effects on various cancer cell lines

  摘要：

  Indole based novel small molecules were designed as potential anticancer agents. Multi step synthesis of these compounds was carried out by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The single crystal X-ray diffraction study was used to confirm the molecular structure of a representative compound unambiguously. Many of these compounds were evaluated for their anti-proliferative properties in vitro against six cancer cell lines as well as noncancerous cells. All these compounds showed selective growth inhibition of cancer cells and several of them were found to be promising with IC50 values in the range of 0.1-1.2 mu M, comparable to the known anticancer drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.050
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 在 sodium hydride 、 potassium carbonate 作用下， 以 丙酮 、 mineral oil 为溶剂， 反应 2.5h， 生成 ethyl 5,6-dimethoxy-1-oxo-2-(prop-2-ynyl)-2,3-dihydro-1H-indene-2-carboxylate
  参考文献：
  名称：

  Pd/C-Mediated Arylation Followed by I₂-Catalyzed Hydration Strategy: Preparation of Functionalized Novel Indanone Derivatives

  摘要：

  A simple and inexpensive synthesis of novel 2-(3-oxo-3-arylpropyl)-2,3-dihydro-1H-inden-1-one derivatives has been achieved via Pd/C-mediated arylation followed by I-2-mediated regioselective hydration of 2-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-ones. A wide variety of 3-aryl substituted 2-propynyl indanone derivatives were conveniently prepared by using 10% Pd/C-PPh3-CuI as a catalyst system, some of which were used to prepare the corresponding ketones via alkyne hydration in the presence of catalytic I-2. In an in vitro study a representative compound showed inhibition of PDE4B (phosphodiesterase type 4B) and binding with this protein in silico

  DOI：

  10.1080/00397911.2013.860554

文献信息

• Pd/C-Mediated Arylation Followed by I₂-Catalyzed Hydration Strategy: Preparation of Functionalized Novel Indanone Derivatives
  作者：Balakrishna Dulla、Sunder Kumar Kolli、Upendar Reddy Chamakura、Giridhar Singh Deora、R. Ramesh Raju、Manojit Pal

  DOI：10.1080/00397911.2013.860554

  日期：2014.5.19

  A simple and inexpensive synthesis of novel 2-(3-oxo-3-arylpropyl)-2,3-dihydro-1H-inden-1-one derivatives has been achieved via Pd/C-mediated arylation followed by I-2-mediated regioselective hydration of 2-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-ones. A wide variety of 3-aryl substituted 2-propynyl indanone derivatives were conveniently prepared by using 10% Pd/C-PPh3-CuI as a catalyst system, some of which were used to prepare the corresponding ketones via alkyne hydration in the presence of catalytic I-2. In an in vitro study a representative compound showed inhibition of PDE4B (phosphodiesterase type 4B) and binding with this protein in silico
• Synthesis of indole based novel small molecules and their in vitro anti-proliferative effects on various cancer cell lines
  作者：Balakrishna Dulla、E. Sailaja、Upendar Reddy CH、Madhu Aeluri、Arunasree M. Kalle、S. Bhavani、D. Rambabu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.12.050

  日期：2014.1

  Indole based novel small molecules were designed as potential anticancer agents. Multi step synthesis of these compounds was carried out by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The single crystal X-ray diffraction study was used to confirm the molecular structure of a representative compound unambiguously. Many of these compounds were evaluated for their anti-proliferative properties in vitro against six cancer cell lines as well as noncancerous cells. All these compounds showed selective growth inhibition of cancer cells and several of them were found to be promising with IC50 values in the range of 0.1-1.2 mu M, comparable to the known anticancer drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.