2-chloro-1-(7-methoxy-1H-indol-3-yl)ethanone | 1018637-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-chloro-1-(7-methoxy-1H-indol-3-yl)ethanone
• 英文别名: Ethanone,2-chloro-1-(7-methoxy-1h-indol-3-yl)-
• CAS: 1018637-79-0
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: HCMJVACHFJQJFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-苄基哌啶 、 2-chloro-1-(7-methoxy-1H-indol-3-yl)ethanone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以53%的产率得到2-(4-benzylpiperidin-1-yl)-1-(7-methoxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Characterization of 3-Substituted-1H-indoles as Ligands of GluN2B-Containing N-Methyl-d-aspartate Receptors

  摘要：

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.

  DOI：

  10.1021/jm2008002
• 作为产物：
  描述：

  7-甲氧基吲哚 、 2-氯-N,N-二甲基乙酰胺 在 三氯氧磷 作用下， 反应 2.5h， 以45%的产率得到2-chloro-1-(7-methoxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Characterization of 3-Substituted-1H-indoles as Ligands of GluN2B-Containing N-Methyl-d-aspartate Receptors

  摘要：

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.

  DOI：

  10.1021/jm2008002

文献信息

• Design, Synthesis and Evaluation of New Indolylpyrimidylpiperazines for Gastrointestinal Cancer Therapy
  作者：Aaron Tan、Maria V. Babak、Gopalakrishnan Venkatesan、Clarissa Lim、Karl-Norbert Klotz、Deron Raymond Herr、Siew Lee Cheong、Stephanie Federico、Giampiero Spalluto、Wei-Yi Ong、Yu Zong Chen、Jason Siau Ee Loo、Giorgia Pastorin

  DOI：10.3390/molecules24203661

  日期：——

  scaffold by switching the position of the carbonyl group, resulting in the formation of both ketone and tertiary amine groups in the new scaffold. Results showed that such modification diminished the A2A activity and instead conferred hA3AR agonistic activity. Among the new mIPP derivatives (3–6), compound 4 showed potential as a hA3AR partial agonist, with an Emax of 30% and EC50 of 2.89 ± 0.55 μM. In

  人类 A3 腺苷受体 hA3AR 与胃肠道癌症有关，其细胞表达增加，因此表明其作为新型抗癌化合物的分子靶点的潜力。我们之前的工作中进行的观察表明，吲哚基嘧啶基哌嗪 (IPP) 中酰胺的羰基对于其人 A2A 腺苷受体 (hA2AAR) 亚型相对于其他 AR 亚型的结合选择性具有重要意义。考虑到这一观察结果，我们通过改变羰基的位置，将吲哚基嘧啶基哌嗪（IPP）支架1（一种非选择性腺苷受体配体）结构修饰为修饰的IPP（mIPP）支架，从而形成新支架中的酮和叔胺基团。结果表明，这种修饰降低了 A2A 活性，反而赋予了 hA3AR 激动活性。在新的 mIPP 衍生物 (3-6) 中，化合物 4 显示出作为 hA3AR 部分激动剂的潜力，其 Emax 为 30%，EC50 为 2.89 ± 0.55 μM。在细胞毒性测定中，与正常细胞相比，化合物4对结直肠癌细胞和肝癌细胞也表现出更高的细胞毒性。总体而
• Synthesis and Biological Characterization of 3-Substituted-1<i>H</i>-indoles as Ligands of GluN2B-Containing <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptors
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Maria Rosa Buemi、Emilio Russo、Giovambattista De Sarro、Lara Costa、Lucia Ciranna、Orazio Prezzavento、Emanuela Arena、Simone Ronsisvalle、Giuseppe Bruno、Alba Chimirri

  DOI：10.1021/jm2008002

  日期：2011.12.22

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.