2-(2-methylamino-ethylaminoformyl)-1H-indole | 1249044-28-7

• 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: 2-(2-methylamino-ethylaminoformyl)-1H-indole
• 英文别名: 2-(2-methylamino-ethylcarbamoyl)-1H-indole；N-[2-(methylamino)ethyl]-1H-indole-2-carboxamide
• CAS: 1249044-28-7
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: LHZMJUMQSMTXSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-2-羧酸 、 N-甲基乙二胺 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-methylamino-ethylaminoformyl)-1H-indole
  参考文献：
  名称：

  Antimicrobial Evaluation, Molecular Docking and ADME Properties of Indole Amide Derivatives

  摘要：

  背景：除了病毒感染外，细菌感染也会导致严重和危及生命的并发症，而药物耐药性是对抗细菌感染的一个重要问题。因此，发现新型抗微生物药物对抗这些感染非常重要。 目标：文献中报道了几项含有吲哚类抗微生物药物的开发研究，提供了强有力的证据表明这些药物对多种微生物具有良好的抗微生物活性。基于这些发现，通过体外测试评估了先前合成的16种吲哚酰胺衍生物的抗微生物性质，针对14种不同的微生物进行了分子对接和计算机预测研究，以确定化合物的结构-活性关系。 方法：通过盘扩散和管稀释法确定化合物的抗微生物活性。使用Autodock vina4.2.6版本对化合物进行分子对接研究，以确定化合物的结构与微生物DNA酶互作之间的关系。还使用Mol inspiration和Swiss ADME预测在线软件程序来确定化合物的药物样性质。 结果：结果表明，一些化合物与参考药物相比表现出相当显著的抗菌和抗真菌活性。这些结果也得到了分子对接研究的支持，并且计算机模拟ADME显示，所有测试化合物都遵守Lipinski的五项规则，并且被CYP450酶代谢。 结论：可以得出结论，这些结果可以作为开发新型基于吲哚的抗微生物药物的参考。

  DOI：

  10.2174/1570180818666211006122758

文献信息

• Synthesis of new indole-2-carboxamide and 3-acetamide derivatives and evaluation their antioxidant properties
  作者：Süreyya Ölgen、Filiz Bakar、Semra Aydin、Doğu Nebioğlu、Serpil Nebioğlu

  DOI：10.3109/14756366.2011.631183

  日期：2013.2.1

  In recent years, antioxidant compounds play an important role as a health-protecting factor. Antioxidants protect cells against the damaging effects of reactive oxygen species (ROS). An imbalance between antioxidants and ROS results in oxidative stress, which leads to cellular damage and it is linked to many vital diseases. It was shown that heme oxygenase (HO) provides efficient cytoprotection against oxidative stress. In this study, a series of indole-2-carboxamide and 3-acetamide derivatives was tested for in vitro effects on HO activity and 2,2-diphenyl-1-picrylhydrazyl (DPPH) inhibition. Among the synthesized compounds, N-[3-(dimethylamino)propyl]-1H-indole-2-carboxamide 3 was found as the most activator of HO and N-(2-(dimethylamino)ethyl)-2-(1H-indol-3-yl)acetamide 8 was found the most potent inhibitor for DPPH at 10(-4) M concentration.
• Antimicrobial Evaluation, Molecular Docking and ADME Properties of Indole Amide Derivatives
  作者：Derya Doğanay、Sevval M. Özcan、Ahmet M. Şentürk、Süreyya Ölgen

  DOI：10.2174/1570180818666211006122758

  日期：2022.5

  Besides the viral infections, bacterial infections can cause serious and lifethreatening complications and drug resistance is an important problem to fight bacterial infections. Therefore, it is important to discover novel antimicrobial agents to fight such infections.

  Several indole containing antimicrobial drug development studies have been reported in literature that provided strong evidence for good antimicrobial activities against a variety of microorganisms. Taken into consideration from these findings, antimicrobial properties of previously synthesized 16 indole amide derivatives were evaluated by in vitro tests against 14 different microorganisms, and also molecular docking and in silico prediction studies were used to identify structure-activity relationship of compounds.

  Antimicrobial activity of compounds was determined by disc diffusion and tube dilution methods. Molecular docking of compounds was studied to determine the relationship between the structure of compounds with DNA gyrase interactions of microorganisms by using the version of Autodock vina 4.2.6. Mol inspiration and Swiss ADME prediction online software programs were also used to identify drug-like properties of compounds.

  The results showed that some compounds exhibited quite pronounced antibacterial and antifungal activities compared to reference drugs. These results were also supported by molecular docking studies and in silico ADME calculations presented that all tested compounds obey Lipinski’s Rule of Five and are metabolized by CYP450 enzymes.

  It can be concluded that these results can be taken as a reference in the development of new indole-based antimicrobial agents.

  背景：除了病毒感染外，细菌感染也会导致严重和危及生命的并发症，而药物耐药性是对抗细菌感染的一个重要问题。因此，发现新型抗微生物药物对抗这些感染非常重要。 目标：文献中报道了几项含有吲哚类抗微生物药物的开发研究，提供了强有力的证据表明这些药物对多种微生物具有良好的抗微生物活性。基于这些发现，通过体外测试评估了先前合成的16种吲哚酰胺衍生物的抗微生物性质，针对14种不同的微生物进行了分子对接和计算机预测研究，以确定化合物的结构-活性关系。 方法：通过盘扩散和管稀释法确定化合物的抗微生物活性。使用Autodock vina4.2.6版本对化合物进行分子对接研究，以确定化合物的结构与微生物DNA酶互作之间的关系。还使用Mol inspiration和Swiss ADME预测在线软件程序来确定化合物的药物样性质。 结果：结果表明，一些化合物与参考药物相比表现出相当显著的抗菌和抗真菌活性。这些结果也得到了分子对接研究的支持，并且计算机模拟ADME显示，所有测试化合物都遵守Lipinski的五项规则，并且被CYP450酶代谢。 结论：可以得出结论，这些结果可以作为开发新型基于吲哚的抗微生物药物的参考。