3-(3-(4-(tert-butyldiphenylsiloxy)butoxy)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydropyridine | 1018845-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-(4-(tert-butyldiphenylsiloxy)butoxy)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydropyridine
• CAS: 1018845-94-7
• 化学式: C₂₈H₃₇N₃O₂SSi
• 分子量: 507.772
• InChiKey: HYRSMSGBJZMUQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.48
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(3-(4-(tert-butyldiphenylsiloxy)butoxy)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydropyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以46%的产率得到4-(4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazol-3-yloxy)butan-1-ol
  参考文献：
  名称：

  Synthesis and evaluation of xanomeline analogs—Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor

  摘要：

  A series of xanomeline analogs were synthesized and evaluated for binding at the M, muscarinic acetylcholine receptor (M-1 receptor). Specifically, compounds that substitute the O-hexyl chain of xanomeline with polar, ionizable, or conformationally restricted moieties were assessed for their ability to bind to the M, receptor in a wash-resistant manner (persistent binding). From our screen, several novel ligands that persistently bind to the M, receptor with greater affinity than xanomeline were discovered. Results indicate that persistent binding may arise not only from hydrophobic interactions but also from ionic interactions with a secondary M, receptor binding site. Herein, a qualitative model that accounts for both binding scenarios is proposed and applied to understand the structural basis to wash-resistant binding and long-acting effects of xanomeline-based compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.058
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-(3-(4-(tert-butyldiphenylsiloxy)butoxy)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Synthesis and evaluation of xanomeline analogs—Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor

  摘要：

  A series of xanomeline analogs were synthesized and evaluated for binding at the M, muscarinic acetylcholine receptor (M-1 receptor). Specifically, compounds that substitute the O-hexyl chain of xanomeline with polar, ionizable, or conformationally restricted moieties were assessed for their ability to bind to the M, receptor in a wash-resistant manner (persistent binding). From our screen, several novel ligands that persistently bind to the M, receptor with greater affinity than xanomeline were discovered. Results indicate that persistent binding may arise not only from hydrophobic interactions but also from ionic interactions with a secondary M, receptor binding site. Herein, a qualitative model that accounts for both binding scenarios is proposed and applied to understand the structural basis to wash-resistant binding and long-acting effects of xanomeline-based compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.058