6-phenylhexan-1-amine hydrochloride | 120375-57-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-phenylhexan-1-amine hydrochloride
• 英文别名: 6-Phenylhexylamine, hydrochloride；6-phenylhexan-1-amine;hydrochloride
• CAS: 120375-57-7
• 化学式: C₁₂H₁₉N*ClH
• 分子量: 213.75
• InChiKey: JYKYEUDNRJFMMW-UHFFFAOYSA-N

物化性质

• 熔点：
  112-116°C (dec.)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-phenylhexan-1-amine hydrochloride 、 zinc(II) chloride 以 乙醚 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  双（苯烷基铵）四氯金属盐的多态性

  摘要：

  通式为C 6 H 5 C n H 2 n NH 3）2 M Cl 4的化合物，其中n＝ 1至10；M = Cd，Cu，Zn和Co; 制备并通过差示扫描量热法表征。用n制备的所有化合物观察到> 1经历了固-固相变，并且固-固相变的高熵表明在高温相中存在相当多的无序。热力学结果的相似性将化合物分为两组：Cd和Cu衍生物以及Co和Zn衍生物。每组内以及各组之间的趋势可归因于苯基基团堆积对热力学行为的影响。

  DOI：

  10.1016/0022-4596(88)90308-8
• 作为产物：
  描述：

  2-(6-phenylhexyl)isoindoline-1,3-dione 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以380 mg的产率得到6-phenylhexan-1-amine hydrochloride
  参考文献：
  名称：

  Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure–Activity Relationship (SAR) Studies

  摘要：

  Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

  DOI：

  10.1021/acs.jmedchem.5b01188

文献信息

• Borrowing hydrogen methodology for the conversion of alcohols into N-protected primary amines and in situ deprotection
  作者：Gareth W. Lamb、Andrew J.A. Watson、Katherine E. Jolley、Aoife C. Maxwell、Jonathan M.J. Williams

  DOI：10.1016/j.tetlet.2009.02.129

  日期：2009.7

  Alcohols have been converted into a range of protected amines including sulfonamides and N-alkylbenzylamine derivatives. Representative examples of deprotection to afford primary amines are also provided.

  醇已被转化为一系列受保护的胺，包括磺酰胺和N-烷基苄基胺衍生物。还提供了脱保护以提供伯胺的代表性实例。
• [EN] BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS<br/>[FR] DÉRIVÉS DE BENZOXAZOLONE EN TANT QU'INHIBITEURS DE LA CÉRAMIDASE ACIDE, ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015173168A1

  公开（公告）日：2015-11-19

  The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

  本发明涉及苯并噁唑酮衍生物作为酸酶抑制剂，含有这些抑制剂的药物组合物以及用于抑制酸酶治疗临床相关的调节神经酰胺水平的疾病的方法。该发明还提供苯并噁唑酮衍生物作为药物在治疗癌症、炎症、疼痛、炎症性疼痛或肺部疾病中的用途。
• [EN] SUBSTITUTED BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS<br/>[FR] DÉRIVÉS DE BENZOXAZOLONE SUBSTITUÉS COMME INHIBITEURS DE LA CÉRAMIDASE ACIDE, ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015173169A1

  公开（公告）日：2015-11-19

  The present invention relates to substituted benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides substituted benzoxazolone derivatives for use in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

  本发明涉及取代苯并噁唑酮衍生物作为酸酰胺酶抑制剂，含有这些抑制剂的药物组合物以及用于治疗调节酰胺水平在临床上相关的疾病的方法。该发明还提供了用于治疗癌症、炎症、疼痛、炎症性疼痛或肺部疾病的取代苯并噁唑酮衍生物。
• Benzoxazolone derivatives as acid ceramidase inhibitors, and their use as medicaments
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：US10226452B2

  公开（公告）日：2019-03-12

  The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

  本发明涉及作为酸性神经酰胺酶抑制剂的苯并恶唑酮衍生物、含有这些抑制剂的药物组合物和抑制酸性神经酰胺酶的方法，用于治疗神经酰胺水平的调节与临床相关的疾病。本发明还提供了用作治疗癌症、炎症、疼痛、炎性疼痛或肺部疾病的药物的苯并恶唑酮衍生物。
• 10.1039/d4ob00534a
  作者：Karapanou, Maria Ioanna、Malliotaki, Dimitra、Stratakis, Manolis

  DOI：10.1039/d4ob00534a

  日期：——

  We present the first example of Au-catalyzed reduction of nitriles into primary amines. In contrast to monohydrosilanes which are completely unreactive, diethylsilane (a dihydrosilane) is capable of reducing aryl or alkyl nitriles into primary amines under catalysis by Au nanoparticles supported on TiO2, via a smooth double hydrosilylation pathway. The produced labile N-disilylamines are readily deprotected

  我们提出了金催化将腈还原成伯胺的第一个例子。与完全不反应的一氢硅烷相比，二乙基硅烷（一种二氢硅烷）能够在 TiO 2负载的 Au 纳米颗粒的催化下，通过平滑的双氢化硅烷化途径将芳基或烷基腈还原为伯胺。产生的不稳定的N-二甲硅烷基胺很容易被Et 2 O中的HCl脱保护，以非常好的至极好的产率形成相应胺的盐酸盐。该催化剂至少可在连续 5 次运行中回收和重复使用。