5,5'-diiodo-3,3'-(4-hydroxy-3-methoxyphenylmethanediyl)bisindole | 1442639-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,5'-diiodo-3,3'-(4-hydroxy-3-methoxyphenylmethanediyl)bisindole
• 英文别名: 4-[bis(5-iodo-1H-indol-3-yl)methyl]-2-methoxyphenol
• CAS: 1442639-62-4
• 化学式: C₂₄H₁₈I₂N₂O₂
• 分子量: 620.228
• InChiKey: KSRZJUMOYIDWIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-碘吲哚 、 香草醛 在 Fe-pillared interlayered clay B 作用下， 以 水 为溶剂， 反应 6.0h， 以72%的产率得到5,5'-diiodo-3,3'-(4-hydroxy-3-methoxyphenylmethanediyl)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

文献信息

• Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents
  作者：Sandip B. Bharate、Jaideep B. Bharate、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ramesh Mudududdla、Rammohan R. Yadav、Baljinder Singh、P.R. Sharma、Sudip Maity、Baldev Singh、Ikhlas A. Khan、Ram A. Vishwakarma

  DOI：10.1016/j.ejmech.2013.02.024

  日期：2013.5

  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.