(1r,4r)-N-benzyl-4-ethylcyclohexan-1-amine | 178363-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1r,4r)-N-benzyl-4-ethylcyclohexan-1-amine
• CAS: 178363-94-5
• 化学式: C₁₅H₂₃N
• 分子量: 217.354
• InChiKey: TVQPCPYQNUXTID-CTYIDZIISA-N

物化性质

• 沸点：
  316.4±11.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1r,4r)-N-benzyl-4-ethylcyclohexan-1-amine 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 trans-4-Ethyl-cyclohexylamin
  参考文献：
  名称：

  Discovery and Optimization of a Compound Series Active against Trypanosoma cruzi, the Causative Agent of Chagas Disease

  摘要：

  Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. It is endemic in South and Central America and recently has been found in other parts of the world, due to migration of chronically infected patients. The current treatment for Chagas disease is not satisfactory, and there is a need for new treatments. In this work, we describe the optimization of a hit compound resulting from the phenotypic screen of a library of compounds against T. cruzi. The compound series was optimized to the level where it had satisfactory pharmacokinetics to allow an efficacy study in a mouse model of Chagas disease. We were able to demonstrate efficacy in this model, although further work is required to improve the potency and selectivity of this series.

  DOI：

  10.1021/acs.jmedchem.9b01852
• 作为产物：
  描述：

  4-乙基环己酮 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (1r,4r)-N-benzyl-4-ethylcyclohexan-1-amine
  参考文献：
  名称：

  Discovery and Optimization of a Compound Series Active against Trypanosoma cruzi, the Causative Agent of Chagas Disease

  摘要：

  Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. It is endemic in South and Central America and recently has been found in other parts of the world, due to migration of chronically infected patients. The current treatment for Chagas disease is not satisfactory, and there is a need for new treatments. In this work, we describe the optimization of a hit compound resulting from the phenotypic screen of a library of compounds against T. cruzi. The compound series was optimized to the level where it had satisfactory pharmacokinetics to allow an efficacy study in a mouse model of Chagas disease. We were able to demonstrate efficacy in this model, although further work is required to improve the potency and selectivity of this series.

  DOI：

  10.1021/acs.jmedchem.9b01852

文献信息

• [EN] TREATMENT OF CHAGAS DISEASE<br/>[FR] TRAITEMENT DE LA MALADIE DE CHAGAS
  申请人：UNIV DUNDEE

  公开号：WO2015189595A1

  公开（公告）日：2015-12-17

  The invention provides compounds of the formula: wherein L1 and L2 are independently selected from O and S; R1 is C3-C6straight or branched alkyl, C3-C7cycloalkyl, C5-C7cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R2 is H, methyl or ethyl; R5 is NRxCORy, NRxRy, CH2COCH3, CH2C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C1-C4alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).

  该发明提供了以下式的化合物：其中L1和L2分别选自O和S；R1为C3-C6直链或支链烷基，C3-C7环烷基，C5-C7环烯基，脱氢胆固醇，苯基或饱和杂环烷基，其中任一可选择地被取代；R2为H，甲基或乙基；R5为NRxCORy，NRxRy，CH2COCH3，CH2C≡N，或者是可选择地被取代的5-或6-成员杂芳基团；X、Y和Z分别为N或CH；Rx分别为H或C1-C4烷基；Ry分别为H，CrC4烷基，苯基或苄基，其中任一可选择地被取代；n为0-3；盐、水合物和N-氧化物，其中可选择的取代基在权利要求中进一步定义。这些化合物在预防或治疗锥虫病等锥虫病方面具有用途。
• A rapid and practical entry into cis-1,4-aminocyclohexanols
  作者：Fabrice Gallou、Bo Han、Jiang Lu、Manuela Seeger-Weibel、Anne-Florence Stoessel、Simon Allmendinger

  DOI：10.1016/j.tetlet.2010.01.029

  日期：2010.3

  A selective and practical approach for the formation of cis-1,4-aminocyclohexanol was developed. The key transformation involves a one-pot imine formation/ Lewis acid-directed imine reduction and results in a highly selective attack of the reducing agent. This simple and practical method is easily amenable to large-scale synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• TREATMENT OF CHAGAS DISEASE
  申请人：UNIVERSITY OF DUNDEE

  公开号：US20170114029A1

  公开（公告）日：2017-04-27

  The invention provides compounds of the formula: wherein L 1 and L 2 are independently selected from O and S; R 1 is C 3 -C 6 straight or branched alkyl, C 3 -C 7 cycloalkyl, C 5 -C 7 cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R 2 is H, methyl or ethyl; R 5 is NRxCORy, NRxRy, CH 2 COCH 3 , CH 2 C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C 1 -C 4 alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).