5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indole-3-carbaldehyde | 1488426-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indole-3-carbaldehyde
• CAS: 1488426-99-8
• 化学式: C₂₁H₁₉FN₄OS
• 分子量: 394.472
• InChiKey: ISSHMRNBUWVPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.71
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indole-3-carbaldehyde 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 N-{{5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}-3,4,5-trimethoxybenzenamine
  参考文献：
  名称：

  Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition

  摘要：

  In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3-yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.018
• 作为产物：
  描述：

  5-氟-1-甲基-1H-吲哚-2-羧酸乙酯 在 potassium carbonate 、 一水合肼 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.76h， 生成 5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Identification and characterization of novel indole based small molecules as anticancer agents through SIRT1 inhibition

  摘要：

  In our pursuit to develop new potential anticancer leads, we designed a combination of structural units of indole and substituted triazole; and a library of 1-{1-methyl-2-[4-phenyl-5-(propan-2-ylsulfanyl)-4H-1,2,4-triazol-3-yl]-1H-indol-3-yl}methanamine derivatives was synthesized and characterized. Cytotoxic evaluations of these molecules over a panel of three human cancer cell lines were carried out. Few molecules exhibited potent growth inhibitory action against the treated cancer cell lines at lower micro molar concentration. An in vitro assay investigation of these active compounds using recombinant human SIRT1 enzyme showed that one of the compounds (IT-14) inhibited the deacetylation activity of the enzyme. The in vivo study of IT-14 exemplified its promising action by reducing the prostate weight to the body weight ratio in prostate hyperplasia animal models. A remarkable decrease in the disruption of histoarchitecture of the prostate tissues isolated from IT-14 treated animal compared to that of the positive control was observed. The molecular interactions with SIRT1 enzyme were also supported by molecular docking simulations. Hence this compound can act as a lead molecule to treat prostatic hyperplasia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.018