N14-tosyl-7,8,13,13b-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5-one | 1316852-04-6

• 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: N14-tosyl-7,8,13,13b-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5-one
• 英文别名: 21-(4-Methylphenyl)sulfonyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one；21-(4-methylphenyl)sulfonyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
• CAS: 1316852-04-6
• 化学式: C₂₅H₂₁N₃O₃S
• 分子量: 443.526
• InChiKey: XOVNPUAOJFJCRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N14-tosyl-7,8,13,13b-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5-one 在 potassium tert-butylate 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以48%的产率得到吴茱萸次碱
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120
• 作为产物：
  描述：

  邻氨基苯甲酸 在 草酰氯 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.33h， 生成 N14-tosyl-7,8,13,13b-tetrahydroindolo-[2',3':3,4]pyrido[2,1-b]quinazolin-5-one
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120

文献信息

• Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues
  作者：Frédéric Pin、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tet.2011.05.120

  日期：2011.8

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.