(1R,3R)-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 171596-48-8

• 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: (1R,3R)-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,3R)-1-(2,3-dihydro-1-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 171596-48-8
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: CEKZLEXKVZHVSL-IEBWSBKVSA-N

物化性质

• 沸点：
  541.0±50.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (1R,3R)-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 (6R,12AR)-2,3,6,7,12,12a-Hexahydro-6-(2,3-Dihydrobenzo(b)Furan-5-yl)-2-Methyl-Pyrazino(2',1':6,1)Pyrido(3,4-b)Indole-1,4-Dione
  参考文献：
  名称：

  Synthesis and SAR of tetracyclic pyrroloquinolones as phosphodiesterase 5 inhibitors

  摘要：

  The synthesis of the fused tetracyclic pyrroloquinolones 9a-i in four steps is described. The PDE5 inhibitory activities of these compounds, their selectivities against PDE1, PDE2, PDE3, PDE4 and PDE6, the preclinical pharmacokinetic assessments and the in vivo efficacy in increasing intracavernosal pressure are presented and discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.044
• 作为产物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 、 D-色氨酸甲酯盐酸盐 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 60.0h， 以17%的产率得到(1R,3R)-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and SAR of tetracyclic pyrroloquinolones as phosphodiesterase 5 inhibitors

  摘要：

  The synthesis of the fused tetracyclic pyrroloquinolones 9a-i in four steps is described. The PDE5 inhibitory activities of these compounds, their selectivities against PDE1, PDE2, PDE3, PDE4 and PDE6, the preclinical pharmacokinetic assessments and the in vivo efficacy in increasing intracavernosal pressure are presented and discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.044

文献信息

• Conversion of tryptophan into ß-carboline derivatives
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2107059A1

  公开（公告）日：2009-10-07

  The invention belongs in the field of organic chemistry and relates to a new shortened Pictet-Spengler type reaction for preparing isomerically pure β-carboline compounds useful for the synthesis of tadalafil.

  这项发明属于有机化学领域，涉及一种用于制备同分异构纯度β-咔啉化合物的新型缩短的Pictet-Spengler型反应，该化合物对于制备他达拉非（tadalafil）非常有用。
• [EN] CONVERSION OF TRYPTOPHAN INTO ß-CARBOLINE DERIVATIVES<br/>[FR] CONVERSION DU TRYPTOPHANE EN DÉRIVÉS DE ?-CARBOLINE
  申请人：LEK PHARMACEUTICALS

  公开号：WO2009121791A1

  公开（公告）日：2009-10-08

  The invention belongs in the field of organic chemistry and relates to a new shortened Pictet- Spengler type reaction for preparing isomerically pure ß-carboline compounds useful for the synthesis of tadalafil.

  该发明属于有机化学领域，涉及一种新的缩短的Pictet-Spengler型反应，用于制备同分异构纯的ß-咔啉化合物，用于合成万艾可。
• Synthesis and SAR of tetracyclic pyrroloquinolones as phosphodiesterase 5 inhibitors
  作者：Weiqin Jiang、Vernon C Alford、Yuhong Qiu、Sheela Bhattacharjee、T.Matthew John、Donna Haynes-Johnson、Patricia J Kraft、Scott G Lundeen、Zhihua Sui

  DOI：10.1016/j.bmc.2003.12.044

  日期：2004.3

  The synthesis of the fused tetracyclic pyrroloquinolones 9a-i in four steps is described. The PDE5 inhibitory activities of these compounds, their selectivities against PDE1, PDE2, PDE3, PDE4 and PDE6, the preclinical pharmacokinetic assessments and the in vivo efficacy in increasing intracavernosal pressure are presented and discussed. (C) 2004 Elsevier Ltd. All rights reserved.