3-(5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-yl)-1H-indole | 1284312-33-9

• 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: 3-(5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-yl)-1H-indole
• 英文别名: 3-[3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazol-5-yl]-1H-indole
• CAS: 1284312-33-9
• 化学式: C₁₉H₁₈N₄O₃
• 分子量: 350.377
• InChiKey: JGQLSLNDDQHREC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚 在 甲酸 、 盐酸羟胺 、 sodium formate 、 potassium carbonate 、 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 11.0h， 生成 3-(5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

  摘要：

  A diverse series of 22 indolyl-1,2,4-triazole congeners (6 and 7) have been synthesized from the reaction of indole-3-carbonitrile (4) or (5) with appropriate acid hydrazides in the presence of potassium carbonate. Synthesized compounds were evaluated for their cytotoxicity against six human cancer cell lines, and some of the compounds displayed promising activity. In particular, 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7i) and 3-(4'-piperidinyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7n) were the most promising and broadly active compounds against the tested cell lines. It was interesting to note that the trimethoxyphenyl analog 7i showed twofold selective cytotoxicity against PaCa2 cell line (IC50 0.8 mu m), whereas piperidinyl analog 7n was found to be selectively cytotoxic against MCF7 cell line (IC50 1.6 mu m). Notably, the 4-fluorophenyl derivative 7c exhibited selective cytotoxicity against PC3 cell line (IC50 4 mu m). The structure-activity relationship study revealed that substituents including 3,4,5-trimethoxyphenyl, 3,4-dimethoxyphenyl, 4-benzyloxy-3-methoxyphenyl, 4-piperidinyl, 4-fluorophenyl and N-methylindole are beneficial for the activity of indolyl-1,2,4-triazoles (6 and 7).

  DOI：

  10.1111/j.1747-0285.2010.01051.x

文献信息

• Design, synthesis, and bioactivity of nortopsentin analogues containing 1,2,4‐triazole moieties
  作者：Xinyu Zhao、Ancai Liao、Fan Zhang、Qi Zhao、Lijia Zhou、Jingjing Fan、Zheng Zhang、Ziwen Wang、Qingmin Wang

  DOI：10.1002/jhet.3817

  日期：2020.2

  activities and fungicidal activities. Compound 3g with higher antiviral activity than nortopsentin D and ribavirin emerged as new antiviral lead compound. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad‐spectrum fungicidal activities. Compounds 3a, 3d, and 3f displayed higher antifungal activities against Cercospora arachidicola Hori than commercial fungicides carbendazim

  植物病害严重且难以控制。迫切需要新型高效农药。设计，合成和评估了一系列降钙素原类似物的抗病毒活性和杀真菌活性。具有比降钙素原D和利巴韦林更高的抗病毒活性的化合物3g作为新的抗病毒先导化合物出现。进一步的杀真菌活性测试表明，降钙素原类似物具有广谱杀真菌活性。化合物3a，3d和3f对Cercospora arachidicola Hori表现出更高的抗真菌活性比商业杀菌剂多菌灵和百菌清大。当前的研究为降钙素原类似物在植物保护中的应用奠定了基础。