(1R,3R)-2-(2-Chloro-acetyl)-1-(3-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

• 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)-2-(2-Chloro-acetyl)-1-(3-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,3R)-2-(2-chloroacetyl)-1-(3-methoxyphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• 化学式: C₂₂H₂₁ClN₂O₄
• 分子量: 412.873
• InChiKey: BDQGQFBZUCUNJC-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-苄基-3-氨基吡咯烷 、 (1R,3R)-2-(2-Chloro-acetyl)-1-(3-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 以 乙醇 为溶剂， 生成 (6R,12aR)-2-((R)-1-Benzyl-pyrrolidin-3-yl)-6-(3-methoxy-phenyl)-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  Design, synthesis and biological activity of β-carboline-based type-5 phosphodiesterase inhibitors

  摘要：

  The SAR of a series of beta-carboline derived type 5 phosphodiesterase inhibitors has been explored and we have discovered compounds with excellent levels of PDE5 potency and selectivity over PDE6. However, the series exhibits low levels of selectivity over PDE11, a phosphodiesterase with unknown function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00159-8
• 作为产物：
  描述：

  D-色氨酸甲酯盐酸盐 在 三乙胺 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 生成 (1R,3R)-2-(2-Chloro-acetyl)-1-(3-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and biological activity of β-carboline-based type-5 phosphodiesterase inhibitors

  摘要：

  The SAR of a series of beta-carboline derived type 5 phosphodiesterase inhibitors has been explored and we have discovered compounds with excellent levels of PDE5 potency and selectivity over PDE6. However, the series exhibits low levels of selectivity over PDE11, a phosphodiesterase with unknown function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00159-8

文献信息

• Design, synthesis and biological activity of β-carboline-based type-5 phosphodiesterase inhibitors
  作者：Graham N. Maw、Charlotte M.N. Allerton、Eugene Gbekor、William A. Million

  DOI：10.1016/s0960-894x(03)00159-8

  日期：2003.4

  The SAR of a series of beta-carboline derived type 5 phosphodiesterase inhibitors has been explored and we have discovered compounds with excellent levels of PDE5 potency and selectivity over PDE6. However, the series exhibits low levels of selectivity over PDE11, a phosphodiesterase with unknown function. (C) 2003 Elsevier Science Ltd. All rights reserved.