3-乙氧基-2-丙氧基苯甲醛 | 100256-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-乙氧基-2-丙氧基苯甲醛
• 英文名称: 3-ethoxy-2-propoxy-benzaldehyde
• 英文别名: 3-Aethoxy-2-propoxy-benzaldehyd；3-Ethoxy-2-propoxybenzaldehyde
• CAS: 100256-89-1
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD05263779
• 分子量: 208.257
• InChiKey: NGLILBQTESXZCG-UHFFFAOYSA-N

物化性质

• 沸点：
  149-150 °C(Press: 11 Torr)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  3-乙氧基-2-丙氧基苯甲醛 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 6.0h， 生成 methyl 5-ethoxy-4-propoxy-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives

  摘要：

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.

  DOI：

  10.1016/j.ejmech.2014.05.043

文献信息

• A rearrangement involving a solid-state melt reaction for the synthesis of multifunctional tetrasubstituted olefins
  作者：Manickam Bakthadoss、Selvakumar Raman、Mohammad Mushaf

  DOI：10.1039/c9ob00639g

  日期：——

  solvent-free intramolecular rearrangement sequence leading towards benzimidazole-tethered tetrasubstituted olefins through a solid-state melt reaction (SSMR) involving imine formation, cyclization, N-allylation and isomerization has been realized for the first time. Interestingly, only water is the byproduct in this novel quadruple domino reaction. Furthermore, the reaction is highly stereoselective, atom

  首次实现了通过亚胺形成，环化，N-烯丙基化和异构化的固态熔融反应（SSMR）导致无苯并咪唑系链的四取代烯烃的无催化剂和无溶剂的分子内重排序列。有趣的是，在这种新颖的四重多米诺反应中，只有水是副产物。此外，该反应本质上是高度立体选择性的，经济的且对环境无害的。
• Profft, Arzneimittel-Forschung/Drug Research, 1959, vol. 9, p. 157,161
  作者：Profft

  DOI：——

  日期：——
• Zur Kenntnis des o-Vanillins und des Novovanillins ( = 2-Oxy-3-äthoxybenzaldehyd) II. Darstellung von 2.3-Dialkoxyphenyl-β-äthylaminen
  作者：Elmar Profft

  DOI：10.1002/ardp.19592920204

  日期：——
• Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives
  作者：Xing-yue Ji、Si-tu Xue、Yue-chen Zhan、Jia-jia Shen、Lin-tao Wu、Jie Jin、Zhen Wang、Zhuo-rong Li

  DOI：10.1016/j.ejmech.2014.05.043

  日期：2014.8

  Based on the chemical structure of Pyrroloquinoline quinone (PQQ), a novel class of indole-2-carboxylate derivatives was designed, synthesized and assayed for antiproliferative activity in cancer cells in vitro. The biological results showed that some derivatives exhibited significant antiproliferative activity against HepG2, A549 and MCF7 cells. Notably, the novel compounds, methyl 6-amino-4-cyclohexylmethoxy-1H-indole-2-carboxylate (6e) and methyl 4-isopropoxy-6-methoxy-1H-indole-2-carboxylate (9l) exhibited more potent antiproliferative activity than the reference drugs PQQ and etoposide in vitro, with IC50 values ranging from 3.78 ± 0.58 to 24.08 ± 1.76 μM. Further biological assay showed that both compounds 6e and 9l increased ROS generation dose-dependently, and induced PARP cleavage in A549 cells. Consequently, 6e and 9l appeared as promising anticancer lead compounds for further optimization.