9-methoxy-5,6,8,9,10,11-hexahydro-7H-5,9:7,11-dimethano-benzo[9]annulen-7-amine | 1607472-83-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9-methoxy-5,6,8,9,10,11-hexahydro-7H-5,9:7,11-dimethano-benzo[9]annulen-7-amine
• 英文别名: 12-Methoxytetracyclo[8.3.1.18,12.02,7]pentadeca-2,4,6-trien-10-amine；12-methoxytetracyclo[8.3.1.18,12.02,7]pentadeca-2,4,6-trien-10-amine
• CAS: 1607472-83-2
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: GRLDJRHCHZRKCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  9-methoxy-5,6,8,9,10,11-hexahydro-7H-5,9:7,11-dimethano-benzo[9]annulen-7-amine 在 正丁基锂 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 0.83h， 生成 1-(benzo[d]thiazol-2-yl)-3-(9-methoxy-5,6,8,9,10,11-hexahydro-7H-5,9:7,11-dimethanobenzo[9]annulen-7-yl)urea
  参考文献：
  名称：

  POLYCYCLIC COMPOUNDS SOLUBLE EPOXIDE HYDROLASE INHIBITORS

  摘要：

  本发明涉及式(I)的可溶性环氧化物酶（sEH）抑制剂，以及其制备过程和治疗适应症。

  公开号：

  EP3584236A1
• 作为产物：
  描述：

  9-methoxy-6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5H-benzocyclononen-7-ol 在 硫酸 、 溶剂黄146 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 9-methoxy-5,6,8,9,10,11-hexahydro-7H-5,9:7,11-dimethano-benzo[9]annulen-7-amine
  参考文献：
  名称：

  Novel benzopolycyclic amines with NMDA receptor antagonist activity

  摘要：

  A new series of benzopolycyclic amines active as NMDA receptor antagonists were synthesized. Most of them exhibited increased activity compared with related analogues previously published. All the tested compounds were more potent than clinically approved amantadine and one of them displayed a lower IC50 value than memantine, an anti-Alzheimer's approved drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.025

文献信息

• Searching for novel applications of the benzohomoadamantane scaffold in medicinal chemistry: Synthesis of novel 11β-HSD1 inhibitors
  作者：Elena Valverde、Constantí Seira、Andrew McBride、Margaret Binnie、F. Javier Luque、Scott P. Webster、Axel Bidon-Chanal、Santiago Vázquez

  DOI：10.1016/j.bmc.2015.11.004

  日期：2015.12

  The structural and physicochemical properties of the adamantane nucleus account for its use as a chemical scaffold in multiple drugs. In the last years, we have developed new polycyclic scaffolds as surrogates of the adamantane group with encouraging results in multiple targets. As adamantane is a common structural feature in several 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) inhibitors, we have explored the ability of the 6,7,8,9,10,11-hexahydro-5H-5,9: 7,11-dimethanobenzo[9]annulen-7-yl scaffold to act as a surrogate of the adamantane nucleus in a novel series of 11 beta-HSD1 inhibitors. Of note, within this family of compounds one derivative is endowed with submicromolar 11 beta-HSD1 inhibitory activity. Molecular modeling studies support the binding of the compounds to the active site of the enzyme. However, a fine tuning of the hydrophobicity of the size-expanded nucleus may be beneficial for the inhibitory potency. (c) 2015 Elsevier Ltd. All rights reserved.
• POLYCYCLIC COMPOUNDS AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Universitat de Barcelona

  公开号：EP3810572A1

  公开（公告）日：2021-04-28
• [EN] POLYCYCLIC COMPOUNDS AS SOLUBLE EPOXIDE HYDROLASE INHIBITORS<br/>[FR] COMPOSÉS POLYCYCLIQUES EN TANT QU'INHIBITEURS D'ÉPOXYDE HYDROLASE SOLUBLE
  申请人：UNIV BARCELONA

  公开号：WO2019243414A1

  公开（公告）日：2019-12-26

  The present invention relates to soluble epoxide hydrolase (sEH) inhibitors of formula (I) to processes for their obtention and to their therapeutic indications.
• POLYCYCLIC COMPOUNDS SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Universitat de Barcelona

  公开号：EP3584236A1

  公开（公告）日：2019-12-25

  The present invention relates to soluble epoxide hydrolase (sEH) inhibitors of formula (I) to processes for their obtention and to their therapeutic indications.

  本发明涉及式(I)的可溶性环氧化物酶（sEH）抑制剂，以及其制备过程和治疗适应症。
• Novel benzopolycyclic amines with NMDA receptor antagonist activity
  作者：Elena Valverde、Francesc X. Sureda、Santiago Vázquez

  DOI：10.1016/j.bmc.2014.03.025

  日期：2014.5

  A new series of benzopolycyclic amines active as NMDA receptor antagonists were synthesized. Most of them exhibited increased activity compared with related analogues previously published. All the tested compounds were more potent than clinically approved amantadine and one of them displayed a lower IC50 value than memantine, an anti-Alzheimer's approved drug. (C) 2014 Elsevier Ltd. All rights reserved.