methyl (1R,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 1041201-54-0

• 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 (1R,3R)-1-(4-ethylphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1041201-54-0
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: JBCUNMDPNMFOHP-RTBURBONSA-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 (1R,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 (1R,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

文献信息

• Synthesis of 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1H-β-carbolines as a new class of antimalarial agents
  作者：Leena Gupta、Kumkum Srivastava、Shubhra Singh、S.K. Puri、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2008.04.030

  日期：2008.6

  A series of hybrid molecules 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1H-beta-carbolines have been synthesized and screened for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum. Compounds 26, 32, and 34 have shown MIC in the range of 0.05-0.11 microM and are in vitro several folds more active than chloroquine

  合成了一系列杂化分子2- [3-（7-氯喹啉-4-基氨基）-烷基] -1-（取代的苯基）-2,3,4,9-四氢-1H-β-咔啉并筛选了它们对恶性疟原虫氯喹敏感菌株的体外抗疟活性。化合物26、32和34的MIC在0.05-0.11 microM的范围内，并且在体外具有比氯喹高几倍的活性。