2-(10H-phenothiazin-10-yl)ethan-1-amine

• 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: 2-(10H-phenothiazin-10-yl)ethan-1-amine
• 英文别名: 2-Phenothiazin-10-ylethanamine
• 化学式: C₁₄H₁₄N₂S
• mdl: MFCD11128056
• 分子量: 242.345
• InChiKey: GEQNUMNORCDKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-(10H-phenothiazin-10-yl)ethan-1-amine 在 甲醇 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.92h， 以38%的产率得到N-methyl-2-phenothiazin-10-yl-ethanamine
  参考文献：
  名称：

  A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

  摘要：

  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.

  DOI：

  10.1021/acschemneuro.8b00242
• 作为产物：
  描述：

  N-[2-(10H-phenothiazin-10-yl)ethyl]-2,2,2-trifluoroacetamide 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以98%的产率得到2-(10H-phenothiazin-10-yl)ethan-1-amine
  参考文献：
  名称：

  吩噻嗪-他林异二聚体：在阿尔茨海默氏病中采用多靶点定向方法

  摘要：

  自2002年以来，没有针对阿尔茨海默氏病的临床候选药物上市。因此，迫切需要一种有效的治疗方法。我们遵循所谓的“多靶标定向配体”方法，设计了36种新型他克林-吩噻嗪异二聚体，并对其体外抗胆碱酯酶特性进行了评估。对这类衍生物的构效关系的评估突出了化合物1dC作为有效的选择性乙酰胆碱酯酶抑制剂，IC 50 = 8 nM，1aA作为有效的丁酰胆碱酯酶抑制剂，IC 50 = 15 nM。选定的杂种，即1aC，1bC，1cC，1dC和2dC表现出对τ （306-336）肽聚集的显着抑制活性，抑制百分比范围为50.5至62.1％。同样，1dC和2dC具有抑制自诱导的Aβ1–42聚集的显着能力。尽管如此，体外研究显示对HepG2细胞和小脑颗粒神经元具有细胞毒性。当以14 mg / kg（ip）对小鼠施用1dC时，未观察到病理生理异常。如体外和体内模型所示，1dC还能够渗透到CNS中。最大大脑浓度接近IC乙

  DOI：

  10.1021/acschemneuro.1c00184

文献信息

• Aza-and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors
  申请人：——

  公开号：US20040034221A1

  公开（公告）日：2004-02-19

  Aza- and polyaza-naphthalenyl carboxamide derivatives including certain quinoline carboxamide and naphthyridine carboxamide derivatives are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  本文描述了包括某些喹啉羧酰胺和萘啶羧酰胺衍生物在内的Aza-和polyaza-萘啶基羧酰胺衍生物，作为HIV整合酶的抑制剂和HIV复制的抑制剂。这些化合物作为化合物或药物可接受的盐，或作为制药组合物中的成分，可用于预防或治疗HIV感染和治疗艾滋病，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。本文还描述了预防、治疗或延迟艾滋病发作的方法以及预防或治疗HIV感染的方法。
• TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS
  申请人：Ohlmeyer Michael

  公开号：US20140213578A1

  公开（公告）日：2014-07-31

  Tricyclic chemical modulators of FOXO transcription factor proteins are disclosed. The compounds are useful to treat cancer, age-onset proteotoxicity, stress-induced depression, inflammation, and acne. The compounds are of the following phenothiazine, dibenzoazepine and annulene and similar genera:

  本文披露了三环化学调节剂对FOXO转录因子蛋白的调节作用。这些化合物可用于治疗癌症、年龄相关蛋白质毒性、压力引起的抑郁症、炎症和痤疮。这些化合物属于以下苯硫噻嗪、二苯并氮杂环和环戊烯类似物系列：
• Synthesis, kinetics and cellular studies of new phenothiazine analogs as potent human-TLK inhibitors
  作者：Delna Johnson、Javeena Hussain、Siddhant Bhoir、Vaishali Chandrasekaran、Parul Sahrawat、Tanya Hans、Md Imtiaz Khalil、Arrigo De Benedetti、Vijay Thiruvenkatam、Sivapriya Kirubakaran

  DOI：10.1039/d2ob02191a

  日期：——

  shown phenothiazines to be potent TLK1B inhibitors. Herein, we report the design and synthesis of a class of phenothiazine molecules and their biological inhibitory effect on hTLK1B/KD through in vitro kinase assays, cellular assays, and in silico studies. We identified a few inhibitors with better inhibition and physio-chemical properties than the reported TLK1B inhibitors using a recombinant human

  蛋白激酶表达模式的改变通常与人类癌症的发生和发展有关。人类样样激酶 (TLK)，包括 TLK1/1B 和 TLK2，是在细胞信号通路中发现的进化激酶，参与 DNA 修复、复制和染色体完整性。几份报告已经证明 TLK1B通过与不同合作伙伴的相互作用在癌症的发展和进展中发挥着众多作用，这种直接关联使它们成为癌症治疗的可行分子靶点。先前的研究表明吩噻嗪是有效的 TLK1B 抑制剂。在此，我们通过体外报道一类吩噻嗪分子的设计合成及其对hTLK1B/KD的生物学抑制作用激酶测定、细胞测定和计算机研究。我们发现了一些抑制剂，其抑制作用和理化特性优于报道的使用重组人杂乱样激酶 1B 激酶结构域 (hTLK1B-KD) 的 TLK1B 抑制剂。非常有趣的是，发现 LNCap 细胞的抑制活性处于亚纳摩尔水平。我们尝试研究新设计的吩噻嗪类似物，以及以高产率产生稳定的催化活性 hTLK1B-KD，代表了朝着未来
• Dispersant additive and lubricating oil composition containing same
  申请人：TEXACO DEVELOPMENT CORPORATION

  公开号：EP0515152A1

  公开（公告）日：1992-11-25

  An additive composition comprising a graft and amine-derivatized copolymer prepared from ethylene and at least one C₃ to C₁₀ alpha-monoolefin and, optionally, a polyene selected from non-conjugated dienes and trienes, the copolymer having a number average molecular weight ranging from 5,500 to 50,000 and having grafted thereon at least 1.8 molecules of a carboxylic acid acylating function per molecule of the copolymer the grafted copolymer being reacted with an amine substituted phenothiazine to form the grafted and amine-derivatized copolymer.

  一种添加剂组合物，包含由乙烯和至少一种 C₃至 C₁₀α-单烯烃以及（可选）一种选自非共轭二烯和三烯的聚烯制备而成的接枝和胺衍生共聚物，该共聚物的平均分子量为 5,500 至 50,000 之间，并且每个共聚物分子至少接枝了 1.8分子的羧酸酰化官能团，接枝的共聚物与胺取代的吩噻嗪反应，形成接枝的胺衍生共聚物。
• Compositions containing derivatives of succinic acylating agent or hydroxyaromatic compounds and methods of using the same
  申请人：THE LUBRIZOL CORPORATION

  公开号：EP0561601A2

  公开（公告）日：1993-09-22

  This invention relates to a composition comprising: a mixture of a brine and a liquid oil, and (A) an emulsifying amount of (i) at least one reaction product of a hydrocarbyl-substituted succinic acylating agent, and at least one of (a) ammonia, (b) an alcohol, (c) an amine, (d) or mixtures thereof, or at least one salt of the reaction product; or (ii) at least one reaction product of a hydroxyaromatic compound, an aldehyde, and an amine. The compositions of the present invention have beneficial emulsification properties. These compositions are useful in drilling, workingover and completing well-bore holes. The well-drilling compositions of the present invention have beneficial viscosity, pumping and suspension properties.

  本发明涉及一种组合物，包括：盐水和液态油的混合物，以及(A)以下物质的乳化量：(i) 至少一种烃基取代的琥珀酰化剂与(a)氨、(b)醇、(c)胺、(d)或其混合物中至少一种的反应产物，或反应产物的至少一种盐；或(ii)至少一种羟基芳香族化合物、醛和胺的反应产物。本发明的组合物具有良好的乳化性能。这些组合物可用于钻井、修井和完成井孔作业。本发明的钻井组合物具有良好的粘度、泵送和悬浮特性。