(5aS,7S,8S,10aS,12S)-7-(3-Allyl-phenyl)-8-methyl-12-(3,4,5-trimethoxy-phenyl)-5,5a,8,9,10,10a,12,13-octahydro-7H-6a,11a,13-triaza-indeno[1,2-b]anthracene-6,11-dione

• 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: (5aS,7S,8S,10aS,12S)-7-(3-Allyl-phenyl)-8-methyl-12-(3,4,5-trimethoxy-phenyl)-5,5a,8,9,10,10a,12,13-octahydro-7H-6a,11a,13-triaza-indeno[1,2-b]anthracene-6,11-dione
• 英文别名: (1S,12S,15S,18S,19S)-18-methyl-19-(3-prop-2-enylphenyl)-12-(3,4,5-trimethoxyphenyl)-10,13,20-triazapentacyclo[11.8.0.03,11.04,9.015,20]henicosa-3(11),4,6,8-tetraene-14,21-dione
• 化学式: C₃₇H₃₉N₃O₅
• 分子量: 605.734
• InChiKey: IWQQSNCBYMQNDD-AUQWBMIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,5S,6S)-6-(3-allylphenyl)-5-methylpiperidine-2-carboxylic acid 、 (1S,3S)-2,3,4,9-tetrahydro-1-(3,4,5-trimethoxyphenyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid 在 2,3,5-三甲基吡啶 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以25%的产率得到(5aS,7S,8S,10aS,12S)-7-(3-Allyl-phenyl)-8-methyl-12-(3,4,5-trimethoxy-phenyl)-5,5a,8,9,10,10a,12,13-octahydro-7H-6a,11a,13-triaza-indeno[1,2-b]anthracene-6,11-dione
  参考文献：
  名称：

  Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets

  摘要：

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).

  DOI：

  10.1021/jo061758p

文献信息

• Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets
  作者：Sivaraman Dandapani、Ping Lan、Aaron B. Beeler、Scott Beischel、Athier Abbas、Bryan L. Roth、John A. Porco,、James S. Panek

  DOI：10.1021/jo061758p

  日期：2006.11.1

  A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).