2β-[(4-chlorophenyl)phenylmethoxymethyl]-3β-(4-fluorophenyl)tropane

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 2β-[(4-chlorophenyl)phenylmethoxymethyl]-3β-(4-fluorophenyl)tropane
• 英文别名: (1R,2S,3S,5S)-2-[[(4-chlorophenyl)-phenylmethoxy]methyl]-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane
• 化学式: C₂₈H₂₉ClFNO
• 分子量: 449.996
• InChiKey: BHFWPQHMNYAIIM-BSCDCSNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基(1R,2S,3S,5S)-3-(4-氟苯基)-8-甲基-8-氮杂双环[3.2.1]辛烷-2-甲酸酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2β-[(4-chlorophenyl)phenylmethoxymethyl]-3β-(4-fluorophenyl)tropane
  参考文献：
  名称：

  Synthesis and Monoamine Transporter Binding of 2-(Diarylmethoxymethyl)-3β-aryltropane Derivatives

  摘要：

  3beta-Aryltropane analogues wherein the 2-position was substituted with various diarylmethoxy-alkyl groups were synthesized and evaluated for binding at the dopamine transporter (DAT), serotonin transporter (SERT), norepinephrine transporter (NET), and muscarinic (M-1) receptors. The 2beta-analogues 9a-i generally demonstrated high to moderate binding affinities (K-i = 34112 nM) at the DAT with good selectivity over SERT, NET, and M-1 receptors. Alternatively, the 2alpha-isomers 10a-i were 10-fold less potent at the DAT with poor selectivity over SERT. These SAR studies provide further evidence for the varied binding requirements of structurally diverse tropane-based ligands and support future studies to elucidate DAT binding requirements in relation to cocaine-like behavioral endpoints.

  DOI：

  10.1021/jm030430a

文献信息

• Synthesis and Monoamine Transporter Binding of 2-(Diarylmethoxymethyl)-3β-aryltropane Derivatives
  作者：Lifen Xu、Santosh S. Kulkarni、Sari Izenwasser、Jonathan L. Katz、Theresa Kopajtic、Stacey A. Lomenzo、Amy Hauck Newman、Mark L. Trudell

  DOI：10.1021/jm030430a

  日期：2004.3.1

  3beta-Aryltropane analogues wherein the 2-position was substituted with various diarylmethoxy-alkyl groups were synthesized and evaluated for binding at the dopamine transporter (DAT), serotonin transporter (SERT), norepinephrine transporter (NET), and muscarinic (M-1) receptors. The 2beta-analogues 9a-i generally demonstrated high to moderate binding affinities (K-i = 34112 nM) at the DAT with good selectivity over SERT, NET, and M-1 receptors. Alternatively, the 2alpha-isomers 10a-i were 10-fold less potent at the DAT with poor selectivity over SERT. These SAR studies provide further evidence for the varied binding requirements of structurally diverse tropane-based ligands and support future studies to elucidate DAT binding requirements in relation to cocaine-like behavioral endpoints.