2-(5-bromo-1H-indol-3-yl)-6-methylquinoline-3-carbonitrile | 1366500-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(5-bromo-1H-indol-3-yl)-6-methylquinoline-3-carbonitrile
• CAS: 1366500-77-7
• 化学式: C₁₉H₁₂BrN₃
• 分子量: 362.228
• InChiKey: IMBCNGGIESKENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-6-甲基喹啉-3-甲腈 、 5-溴吲哚 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以80%的产率得到2-(5-bromo-1H-indol-3-yl)-6-methylquinoline-3-carbonitrile
  参考文献：
  名称：

  C–C bond formation at C-2 of a quinoline ring: Synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors

  摘要：

  A number of 2-(1H-indol-3-yl) quinoline-3-carbonitrile derivatives were synthesized via AlCl3-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC50 similar to 0.89 mu M) is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.027

文献信息

• C–C bond formation at C-2 of a quinoline ring: Synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors
  作者：K. Shiva Kumar、S. Kiran Kumar、B. Yogi Sreenivas、Dhilli Rao Gorja、Ravikumar Kapavarapu、D. Rambabu、G. Rama Krishna、C. Malla Reddy、M.V. Basaveswara Rao、Kishore V.L. Parsa、Manojit Pal

  DOI：10.1016/j.bmc.2012.02.027

  日期：2012.4

  A number of 2-(1H-indol-3-yl) quinoline-3-carbonitrile derivatives were synthesized via AlCl3-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC50 similar to 0.89 mu M) is presented. (C) 2012 Elsevier Ltd. All rights reserved.