3-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-4-(4-pyrrol-1-ylbutoxy)-1,2,5-thiadiazole | 1018845-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-4-(4-pyrrol-1-ylbutoxy)-1,2,5-thiadiazole
• CAS: 1018845-50-5
• 化学式: C₁₆H₂₂N₄OS
• 分子量: 318.443
• InChiKey: XVMMXCXQMIWYSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吡咯 、 3-(3-(4-chlorobutoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-1,2,5,6-tetrahydropyridine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以19%的产率得到3-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-4-(4-pyrrol-1-ylbutoxy)-1,2,5-thiadiazole
  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

文献信息

• Synthesis and evaluation of xanomeline analogs—Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor
  作者：Brian E. Kane、Marianne K.O. Grant、Esam E. El-Fakahany、David M. Ferguson

  DOI：10.1016/j.bmc.2007.10.058

  日期：2008.2.1

  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.