methyl (1S,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 1257308-61-4

• 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: methyl (1S,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1257308-61-4
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: JBCUNMDPNMFOHP-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 、 2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl (1S,3R)-2-[2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl]-1-(4-ethylphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of indolyl glyoxylamides as a new class of antileishmanial agents

  摘要：

  A series of indolylglyoxylamide derivatives have been synthesized and evaluated in vitro against amastigote form of Leishmania donovani. Compound 8c has been identified as the most active analog of the series with IC(50) value of 5.17 mu M and SI value of 31.48, and is several folds more potent than the standard drugs sodium stilbogluconate and pentamidine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.119
• 作为产物：
  描述：

  4-乙基苯甲醛 、 D-色氨酸甲酯 以 甲醇 为溶剂， 生成 methyl (1R,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 、 methyl (1S,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of indolyl glyoxylamides as a new class of antileishmanial agents

  摘要：

  A series of indolylglyoxylamide derivatives have been synthesized and evaluated in vitro against amastigote form of Leishmania donovani. Compound 8c has been identified as the most active analog of the series with IC(50) value of 5.17 mu M and SI value of 31.48, and is several folds more potent than the standard drugs sodium stilbogluconate and pentamidine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.119