1-(3-indolylmethyl)indazole | 28926-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-indolylmethyl)indazole
• 英文别名: 1-((1H-indol-3-yl)methyl)-1H-indazole；1-indol-3-ylmethyl-1H-indazole；1-Indazolyl-(indol-3-yl)methan
• CAS: 28926-22-9
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: DNQUVTVJUQRPFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.61
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  吲唑 、 吲哚-3-甲醇 在 sodium 作用下， 以 水 、 甲苯 为溶剂， 反应 11.0h， 以13.8%的产率得到1-(3-indolylmethyl)indazole
  参考文献：
  名称：

  Synthesis and structural studies of indolylazaindoles and their potency as anticancer chemotherapeutics

  摘要：

  Novel indolylazaindoles were synthesized and characterized by elemental analysis and IR, H-1, C-13, NMR techniques. The single crystal X-ray diffraction data for two new compounds: 3-(3-indolylmethyl)-7-azaindole (2) and 1-(1-benzenesulfonyl-3-indolylmethyl)-7-azaindole (3) were included together with the intermolecular interactions analysis in the solid state. To establish the possible relationship between structure and activity, the set of indole derivatives was extended to include the previously synthesized bisindoles. The cytotoxic/cytostatic activities were evaluated against human leukemia (HL-60) and human prostate (DU145) cancer cells, whilst NHI3T3 fibroblasts were used as non-tumor control cells. Two lead structures 3-(3-Indolylmethyl)-7-azaindole (2) and di-5-iodoindol-3-yl disulfide (6) were discovered as promising compounds in search for new anticancer chemotherapeutics. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.06.083

文献信息

• Decarboxylative Coupling Reaction of 2‐(1 <i>H</i> ‐Indol‐3‐yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives
  作者：Thanigaimalai Pillaiyar、Muhammad Uzair、Saif Ullah、Gregor Schnakenburg、Christa E. Müller

  DOI：10.1002/adsc.201900688

  日期：2019.9.17

  indole alkaloids that exhibit anti‐inflammatory and anti‐cancer effects. Herein, we report on a new, mild and efficient copper(II)‐promoted decarboxylative coupling reaction of 2‐(1H‐indol‐3‐yl)acetic acid derivatives (1 a–h) with a variety of (substituted) indoles (2 a–t) yielding (un)symmetrically substituted DIMs (3 a–z, 3 aa–ai). Reaction of 2‐(1H‐indol‐3‐yl)acetic acid (1 a) with 7‐azaindole led to

  3,3'-二吲哚基甲烷（DIM）是一类重要的吲哚生物碱，具有抗炎和抗癌作用。在此，我们报道了一种新的，温和有效的，由铜（II）促进的2-（1 H-吲哚-3-基）乙酸衍生物（1  a – h）与多种（取代的）吲哚的脱羧偶联反应（2  a – t）产生（非）对称取代的DIM（3  a – z，3  aa – ai）。2-（1 H-吲哚-3-基）乙酸（1  a）与7-氮杂吲哚的反应生成3,3 '连接的DIM类似物5  d时，4，5和6氮杂吲哚与苯并咪唑在N 1氮原子上反应。1  a与1 H-吲唑反应生成1和2-取代的吲唑衍生物的混合物。这种新方法可以大规模合成具有生物活性的DIM。