(1S,3S)-2,3,4,9-tetrahydro-1-(3,4,5-trimethoxyphenyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S)-2,3,4,9-tetrahydro-1-(3,4,5-trimethoxyphenyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid
• 英文别名: (1S,3S)-1-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid；cis-1-(3,4,5-trimethoxy)phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid；(1S,3S)-1-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: SAADZRJBOQGELC-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3S)-2,3,4,9-tetrahydro-1-(3,4,5-trimethoxyphenyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid 、 甲醇 在 氯化亚砜 作用下， 生成 cis-1-(3,4,5-trimethoxy)phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester hydrochloride
  参考文献：
  名称：

  Methyl 1-imidazolecarbodithioate as a thiocarbonyl transfer reagent: a facile one-pot, three-component synthesis of novel 2-substituted-5-aryl-1-oxo-3-thioxo-1,2,3,5,11,11a-hexahydro-6H-imidazo-[1,5-b]-β-carbolines

  摘要：

  An efficient one-pot, three-component synthesis of novel 2-substituted-5-aryl-1-oxo-3-thioxo-1,2,3,5,11,11a-hexahydro-6H-imidazo-[1,5-b]-beta-carbolines employing 1-aryl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylates, primary amines (or amino acid esters) and methyl 1-imidazolecarbodithioate as the thiocarbonyl transfer reagent is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.008
• 作为产物：
  描述：

  methyl (1S,3S)-1-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 Amberlyst A₂₆ hydroxide resin 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以86%的产率得到(1S,3S)-2,3,4,9-tetrahydro-1-(3,4,5-trimethoxyphenyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid
  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

• Discovery of novel phosphatidylcholine-specific phospholipase C drug-like inhibitors as potential anticancer agents
  作者：Chatchakorn Eurtivong、Lisa I. Pilkington、Michelle van Rensburg、Reuben M. White、Harpreet Kaur Brar、Shaun Rees、Emily K. Paulin、Chris Sun Xu、Nabangshu Sharma、Ivanhoe K.H. Leung、Euphemia Leung、David Barker、Jóhannes Reynisson

  DOI：10.1016/j.ejmech.2019.111919

  日期：2020.2

  Phosphatidylcholine-specific phospholipase C (PC-PLC) is a promising target for new anticancer treatment. Herein, we report our work in the discovery of novel drug-like PC-PLC inhibitors. Virtual screening led to the identification of promising hits from four different structural series that contain the molecular scaffold of benzenesulphonamides (10), pyrido[3,4-b]indoles (22), morpholinobenzoic acid (84) and benzamidobenzoic acid (80). 164 structural analogues were tested to investigate the chemical space around the hit series and to generate preliminary structurally activity relationships (SAR). Two of the pyrido[3,4-b]indoles (22_10 and 22_15) had comparable or better potency as D609, an established but non-drug-like PC-PLC inhibitor. Furthermore, three morpholinobenzoic acids (84, 84_4 and 84_5) had superior potency than D609. Therefore, this study paves the way towards the development of drug-like PL-PLC inhibitors as potential anticancer agents. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Methyl 1-imidazolecarbodithioate as a thiocarbonyl transfer reagent: a facile one-pot, three-component synthesis of novel 2-substituted-5-aryl-1-oxo-3-thioxo-1,2,3,5,11,11a-hexahydro-6H-imidazo-[1,5-b]-β-carbolines
  作者：Balendu Singh、G.S.M. Sundaram、Nimesh C. Misra、Hiriyakkanavar Ila

  DOI：10.1016/j.tetlet.2008.11.008

  日期：2009.1

  An efficient one-pot, three-component synthesis of novel 2-substituted-5-aryl-1-oxo-3-thioxo-1,2,3,5,11,11a-hexahydro-6H-imidazo-[1,5-b]-beta-carbolines employing 1-aryl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylates, primary amines (or amino acid esters) and methyl 1-imidazolecarbodithioate as the thiocarbonyl transfer reagent is reported. (C) 2008 Elsevier Ltd. All rights reserved.
• 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).