(S)-3-(1H-indol-3-yl)-N-[1-(pyridin-2-yl)cyclohexylmethyl]-2-[(4-nitrophenyl)-carbamoylamino]propanamide | 1422269-33-7

• 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)-3-(1H-indol-3-yl)-N-[1-(pyridin-2-yl)cyclohexylmethyl]-2-[(4-nitrophenyl)-carbamoylamino]propanamide
• 英文别名: ML-16
• CAS: 1422269-33-7
• 化学式: C₃₀H₃₂N₆O₄
• 分子量: 540.622
• InChiKey: JMYHTPZSIMJBRL-SANMLTNESA-N

物化性质

• 沸点：
  820.6±65.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  142.05
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  [1-(2-pyridinyl)cyclohexyl]methanamine 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (S)-3-(1H-indol-3-yl)-N-[1-(pyridin-2-yl)cyclohexylmethyl]-2-[(4-nitrophenyl)-carbamoylamino]propanamide
  参考文献：
  名称：

  Structure-activity relationship study towards non-peptidic positron emission tomography (PET) radiotracer for gastrin releasing peptide receptors: Development of [18F] (S)-3-(1H-indol-3-yl)-N-[1-[5-(2-fluoroethoxy)pyridin-2-yl]cyclohexylmethyl]-2-methyl-2-[3-(4-nitrophenyl)ureido]propionamide

  摘要：

  Gastrin-releasing peptide receptors (GRP-Rs, also known as bombesin 2 receptors) are overexpressed in a variety of human cancers, including prostate cancer, and therefore they represent a promising target for in vivo imaging of tumors using positron emission tomography (PET). Structural modifications of the nonpeptidic GRP-R antagonist PD-176252 ((S)-1a) led to the identification of the fluorinated analog (S)-3(1H-indol-3-yl)-N-[1-[5-(2-fluoroethoxy) pyridin-2-yl] cyclohexylmethyl]-2-methyl-2-[3-(4-nitrophenyl) ureido] propionamide ((S)-1m) that showed high affinity and antagonistic properties for GRP-R. This antagonist was stable in rat plasma and towards microsomal oxidative metabolism in vitro. (S)-1m was successfully radiolabeled with fluorine-18 through a conventional radiochemistry procedure. [F-18] (S)-1m showed high affinity and displaceable interaction for GRP-Rs in PC3 cells in vitro. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.10.031