5-chloro-7-[(S)-phenyl-(pyridin-2-ylamino)methyl]quinolin-8-ol | 1283651-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-7-[(S)-phenyl-(pyridin-2-ylamino)methyl]quinolin-8-ol
• CAS: 1283651-60-4
• 化学式: C₂₁H₁₆ClN₃O
• 分子量: 361.831
• InChiKey: LQXDDYGFBJHSFV-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-chloro-7-(phenyl(pyridin-2-ylamino)methyl)quinolin-8-ol 在 Chiralcel OD column 作用下， 生成 5-chloro-7-[(R)-phenyl-(pyridin-2-ylamino)methyl]quinolin-8-ol 、 5-chloro-7-[(S)-phenyl-(pyridin-2-ylamino)methyl]quinolin-8-ol
  参考文献：
  名称：

  Separation of Betti Reaction Product Enantiomers: Absolute Configuration and Inhibition of Botulinum Neurotoxin A

  摘要：

  The racemic product of the Betti reaction of 5-chloro-8-hydroxyquinoline, benzaldehyde, and 2-aminopyridine was separated by chiral HPLC to determine which enantiomer inhibited botulinurn neurotoxin serotype A. When the enantiomers unexpectedly proved to have comparable activity, the absolute structures of (+)-(R)-1 and ()-(S)-1 were determined by comparison of calculated and observed circular dichroism spectra. Molecular modeling studies were undertaken in an effort to understand the observed bioactivity and revealed different ensembles of binding modes, with roughly equal binding energies, for the two enantiomers.

  DOI：

  10.1021/ml200028z

文献信息

• Separation of Betti Reaction Product Enantiomers: Absolute Configuration and Inhibition of Botulinum Neurotoxin A
  作者：John H. Cardellina、Rebecca C. Vieira、Vanessa Eccard、Janet Skerry、Vicki Montgomery、Yvette Campbell、Virginia Roxas-Duncan、William Leister、Christopher A. LeClair、David J. Maloney、Daniele Padula、Gennaro Pescitelli、Ilja Khavrutskii、Xin Hu、Anders Wallqvist、Leonard A. Smith

  DOI：10.1021/ml200028z

  日期：2011.5.12

  The racemic product of the Betti reaction of 5-chloro-8-hydroxyquinoline, benzaldehyde, and 2-aminopyridine was separated by chiral HPLC to determine which enantiomer inhibited botulinurn neurotoxin serotype A. When the enantiomers unexpectedly proved to have comparable activity, the absolute structures of (+)-(R)-1 and ()-(S)-1 were determined by comparison of calculated and observed circular dichroism spectra. Molecular modeling studies were undertaken in an effort to understand the observed bioactivity and revealed different ensembles of binding modes, with roughly equal binding energies, for the two enantiomers.