N,N-dimethyl-2-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)-ethan-1-amine | 440-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: N,N-dimethyl-2-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)-ethan-1-amine
• 英文别名: dimethyl-[2-(2-trifluoromethyl-phenothiazin-10-yl)-ethyl]-amine；Dimethyl-[2-(2-trifluormethyl-phenothiazin-10-yl)-aethyl]-amin；10-[2-(dimethylamino)ethyl]-2-(trifluoromethyl)-phenothiazine；N,N-Dimethyl-2-(trifluoromethyl)-10H-phenothiazine-10-(ethanamine)；N,N-dimethyl-2-[2-(trifluoromethyl)phenothiazin-10-yl]ethanamine
• CAS: 440-08-4
• 化学式: C₁₇H₁₇F₃N₂S
• 分子量: 338.397
• InChiKey: PEWCCNQOSORQRU-UHFFFAOYSA-N

物化性质

• 沸点：
  411.2±45.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  31.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间三氟甲基二苯胺 在 碘 、 sulfur 、 sodium amide 作用下， 生成 N,N-dimethyl-2-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)-ethan-1-amine
  参考文献：
  名称：

  Yale et al., Journal of the American Chemical Society, 1957, vol. 79, p. 4375,4377

  摘要：

  DOI：

文献信息

• SMALL MOLECULE COMPOUNDS FOR STEM CELL DIFFERENTIATION
  申请人：Mercola Mark

  公开号：US20100159596A1

  公开（公告）日：2010-06-24

  Methods and small molecule compounds for stem cell differentiation are provided. One example of a class of compounds that may be used is represented by the compound having the structure IA or IB in the form of free base or a pharmaceutically acceptable salt, hydrate, solvate or N-oxide thereof: R 1 is independently hydrogen or (C 1 -C 6 )alkyl; R 2 is independently hydrogen, (C 1 -C 6 )alkyl, aryl, or heteroaryl; R 2′ is independently hydrogen, (C 1 -C 6 )alkyl, CF 3 or C 2 F 5 ; R 3 is independently (C 1 -C 6 )alkyl, aryl, 2-tetrahydrofurylmethyl, an aliphatic tertiary amine, or 4-methoxybenzyl; or R 2 and R 3 may be joined together to form a 5 or 6 member ring lactone; R 4 is independently hydrogen, (C 1 -C 6 )alkyl, a 2- or 4-R 5 -substituted aromatic ring selected from a 4-R 5 -phenyl or a 2-R 5 -5-pyridyl, aryl, heteroaryl, aliphatic tertiary amine or halogen; and R 5 , R 5′ , R 6 , R 6′ , R 7 , R 7′ , are each independently hydrogen, (C 1 -C 6 )alkyl, aryl, optionally substituted phenyl, heteroaryl, a heterocyclic ring, an aliphatic tertiary amine, or halogen.

  提供干细胞分化的方法和小分子化合物。可以使用的一类化合物的一个示例由结构IA或IB表示，以自由碱基或其药学上可接受的盐，水合物，溶剂或N-氧化物的形式存在：R1独立地是氢或（C1-C6）烷基; R2独立地是氢，（C1-C6）烷基，芳基或杂环芳基; R2'独立地是氢，（C1-C6）烷基，CF3或C2F5; R3独立地是（C1-C6）烷基，芳基，2-四氢呋喃甲基，脂肪族三级胺或4-甲氧基苄基; 或者R2和R3可以结合形成5或6元环内酯; R4独立地是氢，（C1-C6）烷基，2-或4-R5-取代的芳环，选自4-R5-苯基或2-R5-5-吡啶基，芳基，杂环芳基，脂肪族三级胺或卤素; R5，R5'，R6，R6'，R7，R7'独立地是氢，（C1-C6）烷基，芳基，可选取代的苯基，杂环芳基，杂环环，脂肪族三级胺或卤素。
• A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential
  作者：Elisa Uliassi、Luis Emiliano Peña-Altamira、Aixa V. Morales、Francesca Massenzio、Sabrina Petralla、Michele Rossi、Marinella Roberti、Loreto Martinez Gonzalez、Ana Martinez、Barbara Monti、Maria Laura Bolognesi

  DOI：10.1021/acschemneuro.8b00242

  日期：2019.1.16

  Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.
• Notes - New Trifluoromethylphenothiazine Derivatives
  作者：Paul Craig、Edward Nodiff、John Lafferty、Glenn Ullyot

  DOI：10.1021/jo01357a618

  日期：1957.6
• US4833138A
  申请人：——

  公开号：US4833138A

  公开（公告）日：1989-05-23
• US9012217B2
  申请人：——

  公开号：US9012217B2

  公开（公告）日：2015-04-21