3-(3-(4-(tert-butoxycarbonyl(methyl)amino)butoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-1,2,5,6-tetrahydropyridine | 1018845-27-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 3-(3-(4-(tert-butoxycarbonyl(methyl)amino)butoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-1,2,5,6-tetrahydropyridine
• CAS: 1018845-27-6
• 化学式: C₁₈H₃₀N₄O₃S
• 分子量: 382.527
• InChiKey: ZKEAWWCWXBTRQP-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  3-(3-(4-(tert-butoxycarbonyl(methyl)amino)butoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-1,2,5,6-tetrahydropyridine 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(3-(4-methylaminobutoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-1,2,5,6-tetrahydropyridine trifluoroacetic acid salt
  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 12.0h， 生成 3-(3-(4-(tert-butoxycarbonyl(methyl)amino)butoxy)-1,2,5-thiadiazol-4-yl)-1-methyl-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