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ethyl (1S,4r)-4-(((2S,5S)-5-(morpholinomethyl)pyrrolidin-2-yl)methoxy)cyclohexane-1-carboxylate | 877758-78-6

中文名称
——
中文别名
——
英文名称
ethyl (1S,4r)-4-(((2S,5S)-5-(morpholinomethyl)pyrrolidin-2-yl)methoxy)cyclohexane-1-carboxylate
英文别名
——
ethyl (1S,4r)-4-(((2S,5S)-5-(morpholinomethyl)pyrrolidin-2-yl)methoxy)cyclohexane-1-carboxylate化学式
CAS
877758-78-6
化学式
C19H34N2O4
mdl
——
分子量
354.49
InChiKey
CTRCODBURMSBNW-XSLAGTTESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.58
  • 重原子数:
    25.0
  • 可旋转键数:
    7.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.95
  • 拓扑面积:
    60.03
  • 氢给体数:
    1.0
  • 氢受体数:
    6.0

反应信息

  • 作为反应物:
    参考文献:
    名称:
    A novel, potent, and orally active VLA-4 antagonist with good aqueous solubility: trans-4-[1-[[2-(5-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetyl]-(5S)-[methoxy(methyl)amino]methyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid
    摘要:
    We have carried out the optimization of substituents at the C-3 or the C-5 position on the pyrrolidine ring of VLA-4 antagonist 3 with 2-(phenylamino)-7-fluorobenzoxazolyl moiety for the purpose of improving in vivo efficacy while maintaining good aqueous solubility. As a result, we successfully increased in vitro activity in the presence of 3% human serum albumin and achieved an exquisite lipophilic and hydrophilic balance of compounds suitable for oral administrative regimen. The modification resulted in the identification of zwitterionic compound 7n with (5S)-[methoxy(methyl) amino] methylpyrrolidine, which significantly alleviated bronchial hyper-responsiveness to acetylcholine chloride at 12.5 mg/kg, p.o. in a murine asthma model and showed favorable aqueous solubility (JP1, 89 mu g/mL; JP2, 462 mu g/mL). Furthermore, this compound showed good oral bioavailability (F = 54%) in monkeys. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2012.11.003
  • 作为产物:
    参考文献:
    名称:
    A novel, potent, and orally active VLA-4 antagonist with good aqueous solubility: trans-4-[1-[[2-(5-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetyl]-(5S)-[methoxy(methyl)amino]methyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid
    摘要:
    We have carried out the optimization of substituents at the C-3 or the C-5 position on the pyrrolidine ring of VLA-4 antagonist 3 with 2-(phenylamino)-7-fluorobenzoxazolyl moiety for the purpose of improving in vivo efficacy while maintaining good aqueous solubility. As a result, we successfully increased in vitro activity in the presence of 3% human serum albumin and achieved an exquisite lipophilic and hydrophilic balance of compounds suitable for oral administrative regimen. The modification resulted in the identification of zwitterionic compound 7n with (5S)-[methoxy(methyl) amino] methylpyrrolidine, which significantly alleviated bronchial hyper-responsiveness to acetylcholine chloride at 12.5 mg/kg, p.o. in a murine asthma model and showed favorable aqueous solubility (JP1, 89 mu g/mL; JP2, 462 mu g/mL). Furthermore, this compound showed good oral bioavailability (F = 54%) in monkeys. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2012.11.003
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