11a-N-tosyl-5-carbapterocarpen | 1311301-31-1

• 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: 11a-N-tosyl-5-carbapterocarpen
• 英文别名: 11-tosyl-6,11-dihydro-5H-benzo[a]carbazole；11-(4-Methylphenyl)sulfonyl-5,6-dihydrobenzo[a]carbazole；11-(4-methylphenyl)sulfonyl-5,6-dihydrobenzo[a]carbazole
• CAS: 1311301-31-1
• 化学式: C₂₃H₁₉NO₂S
• 分子量: 373.475
• InChiKey: AUYZOYAUNISQNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-tetralone tosylhydrazone 在 三氟化硼乙醚 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 11a-N-tosyl-5-carbapterocarpen
  参考文献：
  名称：

  苯并菲歇尔-吲哚反应

  摘要：

  据报道，费休-吲哚合成的新方法是使用反应性中间体苯炔。的添加Ñ甲苯磺酰腙到arynes，通过2-（三甲基硅烷基）三氟甲磺酸苯基前体，导致有效的氟化物激活产生Ñ -arylation。然后将路易斯酸加到相同的反应罐中，然后通过Fischer环化得到N-甲苯磺酰基吲哚产物。

  DOI：

  10.1021/ol201413r

文献信息

• 11a-N-tosyl-5-carbapterocarpans: Synthesis, antineoplastic evaluation and in silico prediction of ADMETox properties
  作者：Joseane A. Mendes、Eduardo J. Salustiano、Carulini de S. Pires、Thaís Oliveira、Julio C.F. Barcellos、Jhonny M.C. Cifuentes、Paulo R.R. Costa、Magdalena N. Rennó、Camilla D. Buarque

  DOI：10.1016/j.bioorg.2018.07.004

  日期：2018.10

  11a-N-tosyl-5-carbapterocarpans (5a-c and 6a-c), 9-N-tosyl-4,4a,9,9a-tetrahydro-3H-carbazole (7), 11a-N-tosyl-5-carbapterocarpen (8) analogues of LQB-223 (4a), were synthesized through palladium catalyzed azaarylation of substituted dihydronaphtalenes (14a-c) and cyclohexadiene (15), respectively, with N-tosyl-oiodoaniline (11). In order to understand the role of the N-tosyl moiety for the pharmacological activity, the azacarbapterocarpen (9) was also synthesized by Fischer indol reaction. The structural requirements at the A and D-rings for the antineoplastic activity toward human leukemias and breast cancer cells were evaluated as well. Substitutions on the A-ring of 4a and analogues alter the effect on different breast cancer subtypes. On the other hand, A-ring is not essential for antileukemic activity since compound 7, which does not contain the A-ring, showed efficacy with high selectivity indices for drug-resistant leukemias. On the other hand, substitutions on the D-ring of 4a for fluorine or iodine did not improve the antileukemic activity. In silico studies concerning Lipinski's rule of five, ADMET properties and drug scores of those compounds were performed, indicating good physicochemical properties for all compounds, in special for compound 7.
• The Benzyne Fischer-Indole Reaction
  作者：Donald McAusland、Sangwon Seo、Didier G. Pintori、Jonathan Finlayson、Michael F. Greaney

  DOI：10.1021/ol201413r

  日期：2011.7.15

  A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.

  据报道，费休-吲哚合成的新方法是使用反应性中间体苯炔。的添加Ñ甲苯磺酰腙到arynes，通过2-（三甲基硅烷基）三氟甲磺酸苯基前体，导致有效的氟化物激活产生Ñ -arylation。然后将路易斯酸加到相同的反应罐中，然后通过Fischer环化得到N-甲苯磺酰基吲哚产物。