1-(indol-3-yl)-2-aminopentane | 132568-70-8

• 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: 1-(indol-3-yl)-2-aminopentane
• 英文别名: 1-(1H-indol-3-yl)pentan-2-amine；α-Propyl-tryptamin；1-indol-3-ylmethyl-butylamine；3-(alpha-Isopropylaminoethyl) indole
• CAS: 132568-70-8
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: OXTXKBQUVJLMPO-UHFFFAOYSA-N

物化性质

• 沸点：
  368.5±17.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(indol-3-yl)-2-aminopentane 在 aluminium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.5h， 生成 1-(indol-3-yl)-2-propylaminopentane
  参考文献：
  名称：

  Structure–activity studies leading to (−)1-(Benzofuran-2-yl)-2-propylaminopentane, ((−)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of Catecholamines and Serotonin in the brain

  摘要：

  The catecholaminergic and serotoninergic neurons in the brain change their performance according to the physiological need via a catecholaminergic/serotoninergic activity enhancer (CAE/SAE) mechanism. Phenylethylamine (PEA), tyramine and tryptamine are the presently known endogenous CAE/SAE substances which enhance the impulse propagation mediated release of catecholamines and serotonin in the brain. A PEA derivative, (-)deprenyl (selegiline), known as a selective inhibitor of MAO-B, is for the time being the only CAE/SAE substance in clinical use. Aiming to develop a selective CAE/SAE substance much more potent than (-)deprenyl, a series of new 1-aryl-2-alkylaminoalkanes, structurally unrelated to PEA and the amphetamines, was designed and prepared. Among them, (-)1-(benzofuran-2-yl)-2-propylaminopentane ((-)BPAP) was selected as a promising candidate substance for further studies. (-)BPAP significantly enhanced in rats the impulse propagation mediated release of catecholamines and serotonin in the brain 30 min after acute injection of 0.36 nmol/kg sc. In the shuttle box, (-)BPAP was in rats about 130 times more potent than (-)deprenyl in antagonizing tetrabenazine induced inhibition of performance. (-)BPAP protected cultured hippocampal neurons from the neurotoxic effect of P-amyloid in 10(-14)-10(-15) concentration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00002-5
• 作为产物：
  描述：

  1-(indol-3-yl)-2-nitro-1-pentene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1-(indol-3-yl)-2-aminopentane
  参考文献：
  名称：

  [EN] BIS-HETEROARYL DERIVATIVES AS MODULATORS OF PROTEIN AGGREGATION
  [FR] DÉRIVÉS BIS-HÉTÉROARYLIQUES EN TANT QUE MODULATEURS DE L'AGRÉGATION DES PROTÉINES

  摘要：

  本发明涉及某些双杂环芳基化合物，含有它们的药物组合物，以及使用它们的方法，包括用于预防、逆转、减缓或抑制蛋白聚集的方法，以及治疗与蛋白聚集相关的疾病的方法，包括帕金森病、阿尔茨海默病、路易体病、帕金森病伴痴呆、额颞型痴呆、亨廷顿病、肌萎缩侧索硬化和多系统萎缩等神经退行性疾病，以及包括黑色素瘤在内的癌症。

  公开号：

  WO2017020010A1

文献信息

• Bis-heteroaryl derivatives as modulators of protein aggregation
  申请人：UCB Biopharma SRL

  公开号：US10975066B2

  公开（公告）日：2021-04-13

  The present invention relates to certain bis-heteroaryl compounds, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, Parkinson's disease with dementia, fronto-temporal dementia, Huntington's Disease, amyotrophic lateral sclerosis, and multiple system atrophy, and cancer including melanoma.

  本发明涉及某些双杂芳基化合物、含有它们的药物组合物以及使用它们的方法，包括预防、逆转、减缓或抑制蛋白质聚集的方法，以及治疗与蛋白质聚集有关的疾病的方法、包括神经退行性疾病，如帕金森病、阿尔茨海默病、路易体病、帕金森病伴痴呆症、前颞叶痴呆症、亨廷顿氏病、肌萎缩性脊髓侧索硬化症和多系统萎缩，以及癌症，包括黑色素瘤。
• BIOCATALYSTS AND METHODS FOR SYNTHESIZING DERIVATIVES OF TRYPTAMINE AND TRYPTAMINE ANALOGS
  申请人：Codexis, Inc.

  公开号：EP2828385B1

  公开（公告）日：2018-02-07
• BIS-HETEROARYL DERIVATIVES AS MODULATORS OF PROTEIN AGGREGATION
  申请人：UCB Biopharma SRL

  公开号：EP3328379B1

  公开（公告）日：2021-07-28