tert-butyl N-(3-aminobutyl)-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]carbamate | 1258833-86-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl N-(3-aminobutyl)-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]carbamate
• CAS: 1258833-86-1
• 化学式: C₁₇H₃₈N₂O₃Si
• 分子量: 346.586
• InChiKey: ARZMGTXAIFZCAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(3-aminobutyl)-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]carbamate 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl (3-((4-bromoisoquinoline)-5-sulfonamido)butyl)(2-hydroxyethyl)carbamate
  参考文献：
  名称：

  IOP-lowering effect of isoquinoline-5-sulfonamide compounds in ocular normotensive monkeys

  摘要：

  Rho-associated coiled coil-formed protein kinase (ROCK) inhibitors are under development as a new class of antiglaucoma agents. Based on the potent ROCK inhibitor H-1152, previously developed by us, we explored the possibility of related compounds as antiglaucoma agents and synthesized seven types of H-1152-inspired isoquinoline-5-sulfonamide compounds (H-0103-H-0107, H-1001, H-1005). Although all of these compounds potently inhibited ROCK (IC50 = 18-48 nM), only H-0104 and H-0106 exerted strong intraocular pressure (IOP)-lowering effects into the eyes of monkeys. These results suggested the possibility that there is no direct relationship between ROCK inhibition and IOP-lowering effects, indicating that the initial screening of compounds based on ROCK inhibitory activity may be an unsuitable strategy for developing antiglaucoma agents with potent IOP-lowering effects. (C) 2014 Elsevier Ltd. All rights rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.085
• 作为产物：
  描述：

  tert-butyl (3-(((benzyloxy)carbonyl)amino)butyl)(2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到tert-butyl N-(3-aminobutyl)-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]carbamate
  参考文献：
  名称：

  IOP-lowering effect of isoquinoline-5-sulfonamide compounds in ocular normotensive monkeys

  摘要：

  Rho-associated coiled coil-formed protein kinase (ROCK) inhibitors are under development as a new class of antiglaucoma agents. Based on the potent ROCK inhibitor H-1152, previously developed by us, we explored the possibility of related compounds as antiglaucoma agents and synthesized seven types of H-1152-inspired isoquinoline-5-sulfonamide compounds (H-0103-H-0107, H-1001, H-1005). Although all of these compounds potently inhibited ROCK (IC50 = 18-48 nM), only H-0104 and H-0106 exerted strong intraocular pressure (IOP)-lowering effects into the eyes of monkeys. These results suggested the possibility that there is no direct relationship between ROCK inhibition and IOP-lowering effects, indicating that the initial screening of compounds based on ROCK inhibitory activity may be an unsuitable strategy for developing antiglaucoma agents with potent IOP-lowering effects. (C) 2014 Elsevier Ltd. All rights rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.085

文献信息

• IOP-lowering effect of isoquinoline-5-sulfonamide compounds in ocular normotensive monkeys
  作者：Kengo Sumi、Yoshihiro Inoue、Masahiro Nishio、Yasuhito Naito、Takamitsu Hosoya、Masaaki Suzuki、Hiroyoshi Hidaka

  DOI：10.1016/j.bmcl.2013.12.085

  日期：2014.2

  Rho-associated coiled coil-formed protein kinase (ROCK) inhibitors are under development as a new class of antiglaucoma agents. Based on the potent ROCK inhibitor H-1152, previously developed by us, we explored the possibility of related compounds as antiglaucoma agents and synthesized seven types of H-1152-inspired isoquinoline-5-sulfonamide compounds (H-0103-H-0107, H-1001, H-1005). Although all of these compounds potently inhibited ROCK (IC50 = 18-48 nM), only H-0104 and H-0106 exerted strong intraocular pressure (IOP)-lowering effects into the eyes of monkeys. These results suggested the possibility that there is no direct relationship between ROCK inhibition and IOP-lowering effects, indicating that the initial screening of compounds based on ROCK inhibitory activity may be an unsuitable strategy for developing antiglaucoma agents with potent IOP-lowering effects. (C) 2014 Elsevier Ltd. All rights rights reserved.