2-(1-butyl-1H-indol-3-yl)ethan-1-amine

• 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-(1-butyl-1H-indol-3-yl)ethan-1-amine
• 英文别名: 2-(1-Butylindol-3-yl)ethanamine
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: HBCYJTZZXZWTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,2-三氯-1-(4,5-二溴-1H-吡咯-2-基)-1-乙酮 、 2-(1-butyl-1H-indol-3-yl)ethan-1-amine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以38%的产率得到4,5-dibromo-N-(2-(1-butyl-1H-indol-3-yl)ethyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

  摘要：

  The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

  DOI：

  10.1016/j.bmc.2019.03.019
• 作为产物：
  描述：

  1-丁基吲哚 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2-(1-butyl-1H-indol-3-yl)ethan-1-amine
  参考文献：
  名称：

  Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

  摘要：

  The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

  DOI：

  10.1016/j.bmc.2019.03.019

文献信息

• Discovery of novel tryptamine derivatives as GluN2B subunit-containing NMDA receptor antagonists via pharmacophore-merging strategy with orally available therapeutic effect of cerebral ischemia
  作者：Jishun Quan、Huali Yang、Fengyun Qin、Yeli He、Jiao Liu、Ying Zhao、Chao Ma、Maosheng Cheng

  DOI：10.1016/j.ejmech.2023.115318

  日期：2023.3

  been designed and synthesized as novel GluN2B subunit-containing NMDA receptor (GluN2B-NMDAR) antagonists, which could simultaneously manifest the receptor-ligand interactions of representative GluN2B-NMDAR antagonists ifenprodil (1) and EVT-101 (3). In the present study, the neuroprotective potential of these compounds was explored through chemical synthesis and pharmacological characterization. Compound

  设计并合成了一系列色胺衍生物作为新型含 GluN2B 亚基的 NMDA 受体 (GluN2B-NMDAR) 拮抗剂，可同时表现出代表性 GluN2B-NMDAR 拮抗剂艾芬地尔 ( 1 ) 和 EVT-101 ( 3)的受体-配体相互作用). 在本研究中，通过化学合成和药理学表征探索了这些化合物的神经保护潜力。化合物Z25的神经保护活性明显优于阳性对照药物（保护百分比：55.8 ± 0.6%对41.0 ± 2.7%），被认为是人 GluN2B-NMDA 受体的有效拮抗剂。从体外判断药理学分析表明，Z25可下调 NMDA 诱导的细胞内 Ca 2+浓度升高，Z25还可上调 NMDA 诱导的细胞内 p-ERK 1/2 表达降低，这表明Z25是 GluN2B-NMDA 受体的拮抗剂。此外，化合物Z25的类药性质的体外初步评价显示出显着的血浆稳定性。基于C57 小鼠的体内药代动力学和药效学研究，化合物Z25表现出相对较短的半衰期和较低的