5-dodecaoxytryptamine hydrochloride | 1432472-54-2

• 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-dodecaoxytryptamine hydrochloride
• 英文别名: 2-(5-dodecoxy-1H-indol-3-yl)ethanamine;hydrochloride
• CAS: 1432472-54-2
• 化学式: C₂₂H₃₆N₂O*ClH
• 分子量: 381.002
• InChiKey: CYKWVKNGCVRLTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  5-羟色胺肌氨酸酐硫酸盐一水合物 在 盐酸 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 50.0h， 生成 5-dodecaoxytryptamine hydrochloride
  参考文献：
  名称：

  5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2016.10.004

文献信息

• Serotonin Analogues as Inhibitors of Breast Cancer Cell Growth
  作者：Jiney Jose、Clint D. J. Tavares、Nancy D. Ebelt、Alessia Lodi、Ramakrishna Edupuganti、Xuemei Xie、Ashwini K. Devkota、Tamer S. Kaoud、Carla L. Van Den Berg、Eric V. Anslyn、Stefano Tiziani、Chandra Bartholomeusz、Kevin N. Dalby

  DOI：10.1021/acsmedchemlett.7b00282

  日期：2017.10.12

  cancer cell lines. Thus, we synthesized a series of novel alkyloxytryptamine analogues, several of which decreased the viability of various human cancer cell lines. Proteomic and metabolomic analyses showed that compounds 6 and 10 induced apoptosis and interfered with signaling pathways that regulate protein translation and survival, such as the Akt/mTOR pathway, in triple-negative breast cancer cells

  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。