(3-ethyl-2-oxaadamant-1-yl)amine | 1160355-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (3-ethyl-2-oxaadamant-1-yl)amine
• 英文别名: 3-Ethyl-2-oxatricyclo[3.3.1.13,7]decan-1-amine
• CAS: 1160355-54-3
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: VSGIKXOKQZBWQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-ethyl-2-oxaadamant-1-yl)amine 在 盐酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 以900 mg的产率得到(3-ethyl-2-oxaadamant-1-yl)amine hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

  摘要：

  The synthesis of several (2-oxaadamant-1-yl) amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.007
• 作为产物：
  描述：

  (3-ethyl-2-oxaadamant-1-yl)hydrazine hydrochloride 在 platinum(IV) oxide 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 (3-ethyl-2-oxaadamant-1-yl)amine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

  摘要：

  The synthesis of several (2-oxaadamant-1-yl) amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.007

文献信息

• [EN] ANALOGS OF ADAMANTYLUREAS AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS<br/>[FR] ANALOGUES D'ADAMANTYLURÉES UTILISÉS EN TANT QU'INHIBITEURS D'HYDROLASE ÉPOXYDE SOLUBLE
  申请人：UNIV BARCELONA

  公开号：WO2017017048A1

  公开（公告）日：2017-02-02

  N-(2-oxaadamantan-1-yl)ureas of formula I, where R3 is H, C1-C3 alkyl, cyclohexyl or phenyl; R is -[CH2]n -Y; n is 0-15; in -[CH2]n - 0-n/3 of the methylene groups are optionally replaced by non adjacent oxygen atoms; and Y is a 3- or 4-substituted phenyl, a 3- or 4-substituted cyclohexyl, a N-substituted piperidin-4-yl, a N-substituted piperidin-3-yl, a di- or tri-fluorosubstituted phenyl, 4-chloro-3-trifluoromethylphenyl, 3-chloro-4-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, or 3-fluoro-4-trifluoromethylphenyl; have epoxide hydrolase (sEH) inhibitory activities similar to those of their N-(adamantan-1-yl)urea analogs. Thus, compounds I are useful as API for the treatment of sEH mediated diseases. Besides, in general, compounds (I) have higher water solubilities and lower melting points, what make them more promising from the point of view of pharmacokinetics and formulation.

  式I的N-(2-氧杂孔莫烷-1-基)脲，其中R3为H、C1-C3烷基、环己基或苯基；R为-[CH2]n-Y；n为0-15；在-[CH2]n-中，0-n/3的亚甲基基团可选择性地被非相邻的氧原子取代；Y为3-或4-取代苯基、3-或4-取代环己基、N-取代哌啶-4-基、N-取代哌啶-3-基、二氟或三氟取代苯基、4-氯-3-三氟甲基苯基、3-氯-4-三氟甲基苯基、4-氟-3-三氟甲基苯基或3-氟-4-三氟甲基苯基；具有环氧化酶（sEH）抑制活性，类似于其N-(孔莫烷-1-基)脲类似物。因此，化合物I可用作治疗sEH介导疾病的API。此外，一般而言，化合物（I）具有较高的水溶性和较低的熔点，这使它们在药代动力学和配方方面更具有前景。
• ANALOGS OF ADAMANTYLUREAS AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Universitat de Barcelona

  公开号：EP3328854A1

  公开（公告）日：2018-06-06
• Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines
  作者：María D. Duque、Pelayo Camps、Lenuta Profire、Silvia Montaner、Santiago Vázquez、Francesc X. Sureda、Jordi Mallol、Marta López-Querol、Lieve Naesens、Erik De Clercq、S. Radhika Prathalingam、John M. Kelly

  DOI：10.1016/j.bmc.2009.02.007

  日期：2009.4

  The synthesis of several (2-oxaadamant-1-yl) amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. (C) 2009 Elsevier Ltd. All rights reserved.