Methyl 4-N,N-dimethylamino-α-azidocinnamate | 136818-57-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl 4-N,N-dimethylamino-α-azidocinnamate
• 英文别名: Methyl 2-azido-3-[4-(dimethylamino)phenyl]prop-2-enoate
• CAS: 136818-57-0
• 化学式: C₁₂H₁₄N₄O₂
• 分子量: 246.269
• InChiKey: FXMRPBYBMBWQNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-N,N-dimethylamino-α-azidocinnamate 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 2.0h， 生成 methyl 6-(dimethylamino)-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
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 对二甲氨基苯甲醛 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 Methyl 4-N,N-dimethylamino-α-azidocinnamate
  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

• Anti-aids piperazines
  申请人：The Upjohn Company

  公开号：US05489593A1

  公开（公告）日：1996-02-06

  The present invention includes diaromatic substituted heterocyclic compounds (III) ##STR1## which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).

  本发明包括二芳基取代的杂环化合物（III）##STR1##，其可用于治疗感染HIV病毒的个体。本发明还包括某些先前一般性披露的抗艾滋病哌嗪基化合物（V）以及一种使用吲哚类化合物（V）和抗艾滋病胺类（X）治疗HIV感染个体的方法。
• 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.