5-氨基甲基二苯并环庚烷 | 7351-49-7

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 中文名称: 5-氨基甲基二苯并环庚烷
• 中文别名: 5-氨基二苯并戊二烷
• 英文名称: (10,11-dihydro-5H-dibenzocycloheptene-5-yl)methylamine
• 英文别名: (10,11-dihydro-5H-dibenzocyclohepten-5-yl)methylamine；10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-methylamine；5-Aminomethyl-10,11-dihydro-5H-dibenzocyclohepten；10,11-Dihydro-5H-dibenzocyclohepten-5-methylamin；10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-methylamin；5-Aminomethyl-dibenzosuberane；2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylmethanamine
• CAS: 7351-49-7
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: YJCNPACNIAQKNY-UHFFFAOYSA-N

物化性质

• 沸点：
  127 °C(Press: 0.15 Torr)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090

制备方法与用途

用途

5-氨基二苯并戊二烷是烷烃类衍生物，可用于有机合成中间体。

反应信息

• 作为反应物：
  描述：

  5-氨基甲基二苯并环庚烷 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 19.5h， 以20%的产率得到N-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylmethyl)-2-(([((4-[(trifluoromethyl)oxy]phenyl)oxy)acetyl]amino)methyl)-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  [EN] ANAPLASTIC LYMPHOMA KINASE MODULATORS AND METHODS OF USE
  [FR] MODULATEURS DE KINASES DE LYMPHOMES ANAPLASIQUES (ALK) ET METHODES D'UTILISATION

  摘要：

  本发明涉及公式I的化合物，其中L、X、Y、Z、R1、R2、R3和R4在此被定义。本发明还提供了使用这些化合物抑制激酶，更具体地抑制ALK激酶的方法。本发明提供了用于调节蛋白激酶酶活性以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学入侵）的化合物。本发明的化合物抑制、调节和/或调节与上述细胞活动相关的激酶受体信号转导途径，本发明包括含有这些化合物的组合物和使用它们治疗激酶依赖性疾病和状况的方法；（公式I）。

  公开号：

  WO2005097765A1
• 作为产物：
  描述：

  二苯并环庚烯酮基氯 在 氨 、 氢气 、 镍 作用下， 以 乙醇 、 乙腈 为溶剂， 60.0~80.0 ℃ 、6.08 MPa 条件下， 反应 6.5h， 生成 5-氨基甲基二苯并环庚烷
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017

文献信息

• Benzocycloheptaisoquinoline derivatives
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US03985751A1

  公开（公告）日：1976-10-12

  Octahydrobenzo[6,7]- (or [5,6]-) cyclohepta-[1,2,3-de]pyride- (or pyrrolo-) [2,1-a]isoquinolines, and decahydrobenzo[6,7]- (or [5,6]-) cyclohepta[1,2,3-de]-azepino[2,1-a]isoquinolines and derivatives thereof, optionally substituted on the pyrrolidine, piperidine or azepine ring. The compounds are useful CNS depressants, anticonvulsant and antiinflammatory agents, and methods for their preparation and use are also disclosed.

  本发明涉及八氢苯并[6,7]-(或[5,6]-)环庚- [1,2,3- de]吡啶- (或吡咯-)[2,1-a]异喹啉和十氢苯并[6,7]- (或[5,6]-)环庚[1,2,3-de]-氮杂[2,1-a]异喹啉及其衍生物，可选地在吡咯啉、哌啶或氮杂环上取代。所述化合物是有用的中枢神经系统抑制剂、抗惊厥和抗炎药物，并且还公开了其制备和使用的方法。
• N6-(Arylalkyl)adenosines. Identification of N6-(9-fluorenylmethyl)adenosine as a highly potent agonist for the adenosine A2 receptor
  作者：B. K. Trivedi、J. A. Bristol、R. F. Bruns、S. J. Haleen、R. P. Steffen

  DOI：10.1021/jm00396a044

  日期：1988.1

  Several N6-(arylalkyl)adenosines related to N6-benzyladenosine were synthesized, and their A1 and A2 adenosine receptor binding affinities were determined. The annulated derivative N6-(1-naphthylmethyl)adenosine resulted in a very potent A2 agonist (A1 Ki = 24 nM, A2 Ki = 9.1 nM), whereas N6-(9-anthracenylmethyl)adenosine was virtually inactive (A1 Ki = 9,000 nM, A2 Ki = 29,000 nM). Interestingly,

  合成了几种与N6-苄基腺苷有关的N6-（芳烷基）腺苷，并确定了它们的A1和A2腺苷受体结合亲和力。环状衍生物N6-（1-萘甲基）腺苷产生非常有效的A2激动剂（A1 Ki = 24 nM，A2 Ki = 9.1 nM），而N6-（9-蒽基甲基）腺苷实际上是无活性的（A1 Ki = 9,000 nM ，A 2 Ki = 29,000 nM）。有趣的是，结构相似的N6-（9-芴基甲基）腺苷是迄今为止报道的最有效的A2激动剂，A2结合的Ki为4.9 nM，A1结合的Ki为5.1 nM。N6-9-芴基腺苷和N6- [2-（9-芴基）乙基]腺苷的同系物对任一腺苷受体显示很少或没有活性。这些试剂对离体大鼠心脏的心率和冠状动脉血流的影响分别与其A1和A2结合亲和力平行。
• 3-Mono-and 3,5-Disubstituted Piperidine Derivatives as Renin Inhibitors
  申请人：Baeschlin Daniel Kaspar

  公开号：US20080194629A1

  公开（公告）日：2008-08-14

  The invention relates to 3,5-piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-piperidine compound, and/or a method of treatment comprising administering a 3,5-piperidine compound, a method for the manufacture of a 3,5-piperidine compound, and novel intermediates and partial steps for their synthesis. Especially, the 3,5-piperidine compounds have the formula I, wherein the symbols have the meanings described in the specification.

  本发明涉及3,5-哌啶化合物，这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病(=紊乱)；该类化合物用于制备用于治疗依赖肾素活性疾病的制药配方；该类化合物用于治疗依赖肾素活性的疾病；包括3,5-哌啶化合物的制药配方和/或包括给予3,5-哌啶化合物的治疗方法，一种制备3,5-哌啶化合物的方法，以及其合成的新中间体和部分步骤。特别地，3,5-哌啶化合物具有式I，其中符号具有规范中描述的含义。
• ANAPLASTIC LYMPHOMA KINASE MODULATORS AND METHODS OF USE
  申请人：Leahy James William

  公开号：US20090186905A1

  公开（公告）日：2009-07-23

  The present invention relates to compounds of the Formula I, wherein L, X, Y, Z, R 1 , R 2 , R 3 and R 4 are defined herein. The invention also provides methods of using the compounds for inhibition of kinases, more specifically ALK kinases. The invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinase receptor signal transduction pathways related to the changes in cellular activities as mentioned above, and the invention includes compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions; (Formula I).

  本发明涉及式I的化合物，其中L、X、Y、Z、R1、R2、R3和R4如本文所定义。本发明还提供使用这些化合物来抑制激酶，更具体地是ALK激酶的方法。本发明提供了用于调节蛋白激酶酶活性以调节细胞活动，如增殖、分化、程序性细胞死亡、迁移和化学入侵的化合物。本发明的化合物抑制、调节和/或调节与上述细胞活动变化相关的激酶受体信号转导通路，本发明包括含有这些化合物的组合物以及使用它们治疗激酶依赖性疾病和病状的方法；（式I）。
• Medium-Chain Lipid Conjugation Facilitates Cell-Permeability and Bioactivity
  作者：Johannes Morstein、Alice Capecchi、Konstantin Hinnah、ByungUk Park、Jerome Petit-Jacques、Reid C. Van Lehn、Jean-Louis Reymond、Dirk Trauner

  DOI：10.1021/jacs.2c07833

  日期：2022.10.12

  the long-chain lipids (LCLs) found in membranes and lipidated proteins. To study the usefulness of such modifications in probe design, we systematically explored the effect of lipid conjugation on five different small molecule chemotypes and find that permeability, cellular retention, subcellular localization, and bioactivity can be significantly modulated depending on the type of lipid tail used. We

  大多数生物活性分子作用于膜蛋白或细胞内靶标，因此需要进入或穿过生物膜。天然产物通常表现出脂质修饰，以促进关键的分子-膜相互作用，并且在许多情况下，在去除脂质基团后，它们的生物活性显着降低。然而，尽管小分子的脂质缀合在自然界中很重要，但在化学生物学和药物化学中并不常用，并且这种缀合的效果尚未得到系统研究。为了了解天然产物中脂质的组成，我们对“天然产物脂质组”进行了化学信息学表征。根据该分析，脂化天然产物主要含有饱和中链脂质（MCL），其明显短于膜和脂化蛋白质中发现的长链脂质（LCL）。为了研究此类修饰在探针设计中的有用性，我们系统地探讨了脂质缀合对五种不同小分子化学型的影响，并发现渗透性、细胞保留、亚细胞定位和生物活性可以根据所用脂质尾的类型进行显着调节。我们证明 MCL 缀合可以使分子具有细胞渗透性并调节其生物活性。在所有探索的化学型中，与 LCL 缀合物相比，MCL 缀合物始终表现出优异的吸收或生物活性，并且与短链脂质