5-butyloxytryptamine hydrochloride | 65-41-8

• 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: 5-butyloxytryptamine hydrochloride
• 英文别名: 2-(5-butoxy-1H-indol-3-yl)ethanamine;hydrochloride
• CAS: 65-41-8
• 化学式: C₁₄H₂₀N₂O*ClH
• 分子量: 268.787
• InChiKey: ZNWFPUMCNUVNSO-UHFFFAOYSA-N

物化性质

• 熔点：
  249-252 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (2-(5-butoxy-1H-indol-3-yl)ethyl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 5-butyloxytryptamine hydrochloride
  参考文献：
  名称：

  5-羟色胺类似物作为乳腺癌细胞生长的抑制剂。

  摘要：

  5-羟色胺（5-羟色胺，5-HT）是乳腺上皮稳态的关键局部调节剂，可通过多种受体发挥作用。据报道，5-羟色胺信号转导的失调通过增强细胞增殖并增强对凋亡的抵抗力而有助于乳腺癌的病理生理。初步分析表明，强效的5-HT1B / 1D血清素受体激动剂5-壬基氧基色胺（5-NT）（一种曲普坦样分子）可诱导乳腺癌细胞系中的细胞死亡。因此，我们合成了一系列新颖的烷氧基色胺类似物，其中一些降低了各种人类癌细胞系的生存能力。蛋白质组学和代谢组学分析表明化合物6和10 在三阴性乳腺癌细胞中诱导凋亡，并干扰调节蛋白质翻译和存活的信号传导途径，例如Akt / mTOR途径。

  DOI：

  10.1021/acsmedchemlett.7b00282

文献信息

• [EN] NOVEL COMPOSITIONS AND METHODS FOR TREATING CANCER<br/>[FR] NOUVELLES COMPOSITIONS ET PROCÉDÉS POUR TRAITER LE CANCER
  申请人：UNIV TEXAS

  公开号：WO2013063492A1

  公开（公告）日：2013-05-02

  Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.

  本文提供了用于治疗疾病的方法和组合物，包括治疗过度增殖性疾病、偏头痛和抑郁症等。
• 5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics
  作者：Katherine C. Faulkner、Katherine A. Hurley、Douglas B. Weibel

  DOI：10.1016/j.bmcl.2016.10.004

  日期：2016.11

  Antibiotic adjuvant therapy represents an exciting opportunity to enhance the activity of clinical antibiotics by co-dosing with a secondary small molecule. Successful adjuvants decrease the concentration of antibiotics used to defeat bacteria, increase activity (in some cases introducing activity against organisms that are drug resistant), and reduce the frequency at which drug-resistant bacteria emerge. We report that 5-alkyloxytryptamines are a new class of broad-spectrum antibacterial agents with exciting activity as antibiotic adjuvants. We synthesized 5-alkyloxytryptamine analogs and found that an alkyl chain length of 6-12 carbons and a primary ammonium group are necessary for the antibacterial activity of the compounds, and an alkyl chain length of 6-10 carbons increased the membrane permeability of Gram-positive and Gram-negative bacteria. Although several of the most potent analogs also have activity against the membranes of human embryonic kidney cells, we demonstrate that below the minimum inhibitory concentration (MIC) where mammalian cell toxicity is low these compounds may be successfully used as adjuvants for chloramphenicol, tetracycline, ciprofloxacin, and rifampicin against clinical strains of Salmonella typhimurium, Acinetobacter baumannii and Staphylococcus aureus, reducing MIC values by as much as several logs. (C) 2016 Elsevier Ltd. All rights reserved.