methyl (13R,15S,17S)-15-(1H-indol-3-ylmethyl)-11-oxa-16-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8-pentaene-15-carboxylate | 1360455-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl (13R,15S,17S)-15-(1H-indol-3-ylmethyl)-11-oxa-16-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8-pentaene-15-carboxylate
• CAS: 1360455-81-7
• 化学式: C₂₆H₂₄N₂O₃
• 分子量: 412.488
• InChiKey: SJGYRYCYVMOBGX-ZNCVFPSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (13R,15S,17S)-15-(1H-indol-3-ylmethyl)-11-oxa-16-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8-pentaene-15-carboxylate 、 间硝基苯甲醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.1h， 以90%的产率得到methyl (1S,3R,14S,16R)-3-(3-nitrophenyl)-18-oxa-2,5-diazaheptacyclo[14.12.0.02,14.04,12.06,11.019,28.022,27]octacosa-4(12),6,8,10,19(28),20,22,24,26-nonaene-14-carboxylate
  参考文献：
  名称：

  An efficient synthesis of highly functionalized novel chromeno[4,3-b]pyrroles and indolizino[6,7-b]indoles as potent antimicrobial and antioxidant agents

  摘要：

  A facile and efficient synthesis of novel chromeno[4,3-b]pyrroles has been accomplished by intramolecular 1,3-dipolar cycloaddition which on subsequent Pictet-Spengler cyclisation in presence of p-toluenesulfonic acid yielded indolizino[6,7-b]indoles. The synthesized chromenopyrroles and indolizinoindoles were evaluated for their antimicrobial and antioxidant activities. Compounds 7b, 7e, 7a and 7d exhibited respectively, good antibacterial and antifungal activities against tested pathogens when compared to reference control. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.061
• 作为产物：
  描述：

  2-羟基-1-萘甲醛 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 12.15h， 生成 methyl (13R,15S,17S)-15-(1H-indol-3-ylmethyl)-11-oxa-16-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8-pentaene-15-carboxylate
  参考文献：
  名称：

  An efficient synthesis of highly functionalized novel chromeno[4,3-b]pyrroles and indolizino[6,7-b]indoles as potent antimicrobial and antioxidant agents

  摘要：

  A facile and efficient synthesis of novel chromeno[4,3-b]pyrroles has been accomplished by intramolecular 1,3-dipolar cycloaddition which on subsequent Pictet-Spengler cyclisation in presence of p-toluenesulfonic acid yielded indolizino[6,7-b]indoles. The synthesized chromenopyrroles and indolizinoindoles were evaluated for their antimicrobial and antioxidant activities. Compounds 7b, 7e, 7a and 7d exhibited respectively, good antibacterial and antifungal activities against tested pathogens when compared to reference control. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.061

文献信息

• An efficient synthesis of highly functionalized novel chromeno[4,3-b]pyrroles and indolizino[6,7-b]indoles as potent antimicrobial and antioxidant agents
  作者：Natarajan Arumugam、Raghavachary Raghunathan、Abdulrahman I. Almansour、Usama Karama

  DOI：10.1016/j.bmcl.2011.12.061

  日期：2012.2

  A facile and efficient synthesis of novel chromeno[4,3-b]pyrroles has been accomplished by intramolecular 1,3-dipolar cycloaddition which on subsequent Pictet-Spengler cyclisation in presence of p-toluenesulfonic acid yielded indolizino[6,7-b]indoles. The synthesized chromenopyrroles and indolizinoindoles were evaluated for their antimicrobial and antioxidant activities. Compounds 7b, 7e, 7a and 7d exhibited respectively, good antibacterial and antifungal activities against tested pathogens when compared to reference control. (C) 2011 Elsevier Ltd. All rights reserved.