(S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid tert-butyl ester | 334620-24-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid tert-butyl ester
• CAS: 334620-24-5
• 化学式: C₃₀H₃₈N₆O₅S
• 分子量: 594.735
• InChiKey: ABJVQEVFMIJPHL-OZXSUGGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  142.62
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/αIIbβ3 dual activity and improved water solubility

  摘要：

  In order to optimize our novel integrin alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonists, spatial screening at the N-terminus was performed. The alpha(v)beta(3) antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against alpha(IIb)beta(3) was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against alpha(v)beta(3), and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the alpha(v)beta(3) receptor were performed to confirm the SAR findings. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.055
• 作为产物：
  描述：

  (3S)-氮杂环庚-3-胺 在 硫酸 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (S)-2-Benzenesulfonylamino-3-{4-[(S)-3-(pyrimidin-2-ylamino)-azepan-1-yl]-benzoylamino}-propionic acid tert-butyl ester
  参考文献：
  名称：

  Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/αIIbβ3 dual activity and improved water solubility

  摘要：

  In order to optimize our novel integrin alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonists, spatial screening at the N-terminus was performed. The alpha(v)beta(3) antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against alpha(IIb)beta(3) was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against alpha(v)beta(3), and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the alpha(v)beta(3) receptor were performed to confirm the SAR findings. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.055