7-{(1R,2R)-2-[3-(4-Amino-3-iodo-phenyl)-propylamino]-cyclopentyl}-heptanoic acid | 107539-84-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-{(1R,2R)-2-[3-(4-Amino-3-iodo-phenyl)-propylamino]-cyclopentyl}-heptanoic acid
• CAS: 107539-84-4
• 化学式: C₂₁H₃₃IN₂O₂
• 分子量: 472.41
• InChiKey: MEBXFIFZPNLIFS-YLJYHZDGSA-N

物化性质

• 沸点：
  585.9±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.35
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-{(1R,2R)-2-[3-(4-Amino-3-iodo-phenyl)-propylamino]-cyclopentyl}-heptanoic acid 在 sodium azide 、 溶剂黄146 、 sodium nitrite 作用下， 生成 dl-16-(4'-azido-3'-iodophenyl)-17,18,19,20-tetranor-13-azaprostanoic acid
  参考文献：
  名称：

  Preparation and biological evaluation of a potential photoaffinity label for the prostaglandin H2/thromboxane A2 receptor

  摘要：

  Two aromatic azides (24 and 26) were prepared as potential photoaffinity probes for the PGH2/TXA2 receptor. The compounds are based on the well-characterized PGH2/TXA2 receptor antagonist 13-azaprostanoic acid, with the terminus of its lower side chain replaced with phenoxy (24) or benzyl (26) azide functionality. The two compounds were shown to irreversibly inhibit platelet function after photolysis and resuspension. However, of the two aromatic azides, only the benzyl derivative 26 appeared to be selective for the prostaglandin pathway. The latter compound was also prepared as the aromatic 125I (29) derivative, which may ultimately prove useful as a labeled probe for the identification and isolation of the putative TXA2/PGH2 receptor.

  DOI：

  10.1021/jm00388a029
• 作为产物：
  描述：

  3-(4-硝基苯基)-1-丙胺 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 sodium acetate buffer 、 4 A molecular sieve 、 氢气 、 chloroamine-T 、 sodium iodide 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、241.32 kPa 条件下， 反应 28.67h， 生成 7-{(1R,2R)-2-[3-(4-Amino-3-iodo-phenyl)-propylamino]-cyclopentyl}-heptanoic acid
  参考文献：
  名称：

  Preparation and biological evaluation of a potential photoaffinity label for the prostaglandin H2/thromboxane A2 receptor

  摘要：

  Two aromatic azides (24 and 26) were prepared as potential photoaffinity probes for the PGH2/TXA2 receptor. The compounds are based on the well-characterized PGH2/TXA2 receptor antagonist 13-azaprostanoic acid, with the terminus of its lower side chain replaced with phenoxy (24) or benzyl (26) azide functionality. The two compounds were shown to irreversibly inhibit platelet function after photolysis and resuspension. However, of the two aromatic azides, only the benzyl derivative 26 appeared to be selective for the prostaglandin pathway. The latter compound was also prepared as the aromatic 125I (29) derivative, which may ultimately prove useful as a labeled probe for the identification and isolation of the putative TXA2/PGH2 receptor.

  DOI：

  10.1021/jm00388a029