5,5'-diiodo-3,3'-(naphth-1-yl-methanediyl)bisindole | 1442639-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,5'-diiodo-3,3'-(naphth-1-yl-methanediyl)bisindole
• 英文别名: 5-iodo-3-[(5-iodo-1H-indol-3-yl)-naphthalen-1-ylmethyl]-1H-indole
• CAS: 1442639-67-9
• 化学式: C₂₇H₁₈I₂N₂
• 分子量: 624.262
• InChiKey: MBNXPXDVQKWADG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-碘吲哚 、 1-萘甲醛 在 Fe-pillared interlayered clay B 作用下， 以 水 为溶剂， 反应 8.0h， 以62%的产率得到5,5'-diiodo-3,3'-(naphth-1-yl-methanediyl)bisindole
  参考文献：
  名称：

  Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents

  摘要：

  An efficient protocol for synthesis of 3,3'-diindolylmethanes using recyclable Fe-pillared interlayered clay (Fe-PILC) catalyst under aqueous medium has been developed. All synthesized 3,3'-diindolylmethanes showed promising antileishmanial activity against Leishmania donovani promastigotes as well as axenic amastigotes. Structure-activity relationship analysis revealed that nitroaryl substituted diindolylmethanes showed potent antileishmanial activity. The 4-nitrophenyl linked 3,3'-diindolylmethane 8g was found to be the most potent antileishmanial analog showing IC50 values of 7.88 and 8.37 mu M against both L donovani promastigotes and amastigotes, respectively. Further, a pharmacophore based QSAR model was established to understand the crucial molecular features of 3,3'-diindolylmethanes essential for potent antileishmanial activity. These compounds also exhibited promising antifungal activity against Cryptococcus neoformans, wherein fluorophenyl substituted 3,3'-diindolylmethanes were found to be most potent antifungal agents. Developed synthetic protocol will be useful for economical and eco-friendly synthesis of potent antileishmanial and antifungal 3,3'-diindolylmethane class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.024