(R)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propionamide | 861445-46-7

• 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: (R)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propionamide
• CAS: 861445-46-7
• 化学式: C₂₀H₁₉N₃O₅
• 分子量: 381.388
• InChiKey: XPKNBTLQXOIFCL-WBMJQRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  118.8
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propionamide 在 N-甲基吗啉 、 一水合肼 、 氯甲酸异丁酯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [(S)-2-{(S)-2-[(R)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-ethoxycarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Structure–activity relationships of novel endomorphin-2 analogues with N–O turns induced by α-aminoxy acids

  摘要：

  Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2, EM-2) is a putative endogenous mu-opioid receptor ligand. To study the structure-activity relationship against its receptor, we introduced N-O turns into EM-2 and got the analogues with potent affinities for p-opioid receptor. Our results indicated that N-O turn structures at the PrO2-aminoxy-Phe(3) position of EM-2 analogues played important roles for their affinities. These novel analogues with N-O turns provided a new approach to develop potent analgesics related to EM-2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.050
• 作为产物：
  描述：

  (2R)-A-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)氧基]-丙酸-1,1-二甲基乙酸乙酯 在 N-甲基吗啉 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 反应 2.0h， 生成 (R)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propionamide
  参考文献：
  名称：

  Structure–activity relationships of novel endomorphin-2 analogues with N–O turns induced by α-aminoxy acids

  摘要：

  Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2, EM-2) is a putative endogenous mu-opioid receptor ligand. To study the structure-activity relationship against its receptor, we introduced N-O turns into EM-2 and got the analogues with potent affinities for p-opioid receptor. Our results indicated that N-O turn structures at the PrO2-aminoxy-Phe(3) position of EM-2 analogues played important roles for their affinities. These novel analogues with N-O turns provided a new approach to develop potent analgesics related to EM-2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.050