2-(2-cyclopropyl-2-oxoethyl)isoquinolin-2-ium bromide | 1224575-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-cyclopropyl-2-oxoethyl)isoquinolin-2-ium bromide
• 英文别名: 1-Cyclopropyl-2-isoquinolin-2-ium-2-ylethanone;bromide
• CAS: 1224575-18-1
• 化学式: Br*C₁₄H₁₄NO
• 分子量: 292.175
• InChiKey: LKBIUVMXXHSLET-UHFFFAOYSA-M

物化性质

• 熔点：
  187-188 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-cyclopropyl-2-oxoethyl)isoquinolin-2-ium bromide 、 马来酸二甲酯 在 tetrakispyridinecobalt(II) di(chromate) 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以76%的产率得到dimethyl 3-cyclopropylcarbonylpyrrolo[1,2-b]isoquinoline-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line

  摘要：

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.02.056
• 作为产物：
  描述：

  异喹啉 、 2-溴-1-环丙基乙酮 以 乙酸乙酯 为溶剂， 反应 48.5h， 以99%的产率得到2-(2-cyclopropyl-2-oxoethyl)isoquinolin-2-ium bromide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line

  摘要：

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.02.056

文献信息

• A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and <i>N</i>-ylides: access to pyrrolo[2,1-<i>a</i>]quinolines, pyrrolo[2,1-<i>a</i>]phthalazines and indolizines
  作者：Jing Zheng、Xiaojie He、Hong Xu、Hua Liu、Weiran Yang

  DOI：10.1039/d0ob01739f

  日期：——

  A sequential [3 + 2] annulation of prop-2-ynylsulfonium salt and N-ylides was developed, leading to the formation of a series of pyrrolo[2,1-a]quinolines, pyrrolo[2,1-a]phthalazines and indolizines. The protocol featured the simultaneous one-pot formation of three new C–C bonds in moderate yields under mild conditions. In this reaction, the prop-2-ynylsulfonium salts acted as the C2 synthons and sulfide

  开发了丙-2-炔基锍盐和N-叶立德的顺序[3 + 2]环化，导致形成一系列吡咯并[2,1 - a ]喹啉、吡咯并[2,1 - a ]酞嗪和中氮茚。该协议的特点是在温和条件下以中等收益率同时一锅形成三个新的 C-C 键。在该反应中，prop-2-ynyl 锍盐充当 C2 合成子，硫化物充当离去基团。所得产物可作为合成多种化合物的有用前体。
• Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line
  作者：Yong-Miao Shen、Peng-Cheng Lv、Wu Chen、Peng-Gang Liu、Ming-Zhu Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.02.056

  日期：2010.7

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.