[(1R,4S)-2-azabicyclo[2.2.1]heptan-4-yl]methanamine | 1220533-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [(1R,4S)-2-azabicyclo[2.2.1]heptan-4-yl]methanamine
• CAS: 1220533-67-4
• 化学式: C₇H₁₄N₂
• 分子量: 126.202
• InChiKey: RGMINRVOFHIEGB-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2,8-二(三氟甲基)-4-喹啉基]环氧乙烷 、 [(1R,4S)-2-azabicyclo[2.2.1]heptan-4-yl]methanamine 以 乙醇 为溶剂， 130.0 ℃ 、1.21 MPa 条件下， 以78%的产率得到2-((1S,4R)-2-azabicyclo[2.2.1]heptan-4-ylmethylamino)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)ethanol
  参考文献：
  名称：

  Structure–activity relationships amongst 4-position quinoline methanol antimalarials that inhibit the growth of drug sensitive and resistant strains of Plasmodium falciparum

  摘要：

  Utilizing mefloquine as a scaffold, a next generation quinoline methanol (NGQM) library was constructed to identify early lead compounds that possess biological properties consistent with the target product pro. le for malaria chemoprophylaxis while reducing permeability across the blood-brain barrier. The library of 200 analogs resulted in compounds that inhibit the growth of drug sensitive and resistant strains of Plasmodium falciparum. Herein we report selected chemotypes and the emerging structure activity relationship for this library of quinoline methanols. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.01.001

文献信息

• Structure–Activity Relationships of 4-Position Diamine Quinoline Methanols as Intermittent Preventative Treatment (IPT) against <i>Plasmodium falciparum</i>
  作者：Erin Milner、Sean Gardner、Jay Moon、Kristina Grauer、Jennifer Auschwitz、Ian Bathurst、Diana Caridha、Lucia Gerena、Montip Gettayacamin、Jacob Johnson、Michael Kozar、Patricia Lee、Susan Leed、Qigui Li、William McCalmont、Victor Melendez、Norma Roncal、Richard Sciotti、Bryan Smith、Jason Sousa、Anchalee Tungtaeng、Peter Wipf、Geoffrey Dow

  DOI：10.1021/jm200647u

  日期：2011.9.22

  A library of diamine quinoline methanols were designed based on the mefloquine scaffold. The systematic variation of the 4-position amino alcohol side chain led to analogues that maintained potency while reducing accumulation in the central nervous system (CNS). Although the mechanism of action remains elusive, these data indicate that the 4-position side chain is critical for activity and that potency (as measured by IC(90)) does not correlate with accumulation in the CNS. A new lead compound, (S)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)-2-(2-(cyclopropylamino)ethylamino)ethanol (WR621308), was identified with single dose efficacy and substantially lower permeability across MDCK cell monolayers than mefloquine. This compound could be appropriate for intermittent preventative treatment (IPTx) indications or other malaria treatments currently approved for mefloquine.