S,S'-(1-(5-(4-phenylpiperazin-1-yl)pentyl)-1H-indol-3-yl)methylene diethanethioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: S,S'-(1-(5-(4-phenylpiperazin-1-yl)pentyl)-1H-indol-3-yl)methylene diethanethioate
• 英文别名: S-[acetylsulfanyl-[1-[5-(4-phenylpiperazin-1-yl)pentyl]indol-3-yl]methyl] ethanethioate
• 化学式: C₂₈H₃₅N₃O₂S₂
• 分子量: 509.737
• InChiKey: XWKCLMRUBUCXPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(5-bromopentyl)indole-3-carbaldehyde 在 tetra-N-butylammonium tribromide 、 N,N-二异丙基乙胺 作用下， 以 乙酸酐 为溶剂， 生成 S,S'-(1-(5-(4-phenylpiperazin-1-yl)pentyl)-1H-indol-3-yl)methylene diethanethioate
  参考文献：
  名称：

  gem -Dithioacetylated indole derivatives as novel antileishmanial agents

  摘要：

  In this communication we report a serendipitously discovered hybrid molecule 1, combining fragment of 3 (an in vivo active antileishmanial molecule) with H2S donor moiety (known for bimodal behavior of cytoprotection and apoptosis), as antileishmanial agent. Compound 1 suppresses 99.82% parasitemia of L donovani infected macrophages at 12.5 mu g/ml without even deforming them (CC50 > 100 mu g/ml). This compound appears cytotoxic for intracellular amastigotes while cytoprotective to host macrophages. The concept can be utilized to develop high therapeutic index NCE (New Chemical Entities) for other macrophage mediated diseases like tuberculosis and cancer. (c) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.018

文献信息

• gem -Dithioacetylated indole derivatives as novel antileishmanial agents
  作者：Sharad Porwal、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2017.09.018

  日期：2017.10

  In this communication we report a serendipitously discovered hybrid molecule 1, combining fragment of 3 (an in vivo active antileishmanial molecule) with H2S donor moiety (known for bimodal behavior of cytoprotection and apoptosis), as antileishmanial agent. Compound 1 suppresses 99.82% parasitemia of L donovani infected macrophages at 12.5 mu g/ml without even deforming them (CC50 > 100 mu g/ml). This compound appears cytotoxic for intracellular amastigotes while cytoprotective to host macrophages. The concept can be utilized to develop high therapeutic index NCE (New Chemical Entities) for other macrophage mediated diseases like tuberculosis and cancer. (c) 2017 Elsevier Ltd. All rights reserved.