9-ethyl-γ-carboline-6-sulfonyl chloride | 1158629-04-9

• 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: 9-ethyl-γ-carboline-6-sulfonyl chloride
• CAS: 1158629-04-9
• 化学式: C₁₃H₁₁ClN₂O₂S
• 分子量: 294.762
• InChiKey: HWILEDUODQLPBV-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±38.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-甲基-1H-吲哚-5-胺 、 9-ethyl-γ-carboline-6-sulfonyl chloride 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 以48%的产率得到9-ethyl-N-(1-methyl-indol-5-yl)-γ-carboline-6-sulfonamide
  参考文献：
  名称：

  Design, synthesis, and quantitative structure–activity relationship of cytotoxic γ-carboline derivatives

  摘要：

  Three series of gamma-carboline derivatives were designed and synthesized. All the compounds were tested for their cytotoxic activities in vitro against five human tumor cell lines (A549, SGC, HCT116, MCF-7, K562) and one multi-drug resistant subline (K562R). Most compounds showed moderate to potent cytotoxic activities against the tested cell lines. Sulfonate 11f exhibited more potent cytotoxic activities against almost all of the tested cells in comparison with the positive control, taxol, with IC50 values ranging from 0.15 to 4.5 mu M. The structure-activity relationships were discussed and a statistically reliable QSAR model (r(2) = 0.936, q(2) = 0.581) was established by the CoMFA analysis performed using the cytotoxic data against K562 cell line as a template. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.037
• 作为产物：
  描述：

  在 五氯化磷 、 三氯氧磷 作用下， 反应 4.0h， 生成 9-ethyl-γ-carboline-6-sulfonyl chloride
  参考文献：
  名称：

  Design, synthesis, and quantitative structure–activity relationship of cytotoxic γ-carboline derivatives

  摘要：

  Three series of gamma-carboline derivatives were designed and synthesized. All the compounds were tested for their cytotoxic activities in vitro against five human tumor cell lines (A549, SGC, HCT116, MCF-7, K562) and one multi-drug resistant subline (K562R). Most compounds showed moderate to potent cytotoxic activities against the tested cell lines. Sulfonate 11f exhibited more potent cytotoxic activities against almost all of the tested cells in comparison with the positive control, taxol, with IC50 values ranging from 0.15 to 4.5 mu M. The structure-activity relationships were discussed and a statistically reliable QSAR model (r(2) = 0.936, q(2) = 0.581) was established by the CoMFA analysis performed using the cytotoxic data against K562 cell line as a template. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.037