2-[1'-[(2-Methylpropan-2-yl)oxycarbonyl]-3-oxospiro[1,5-dihydro-2-benzazepine-4,2'-pyrrolidine]-2-yl]acetic acid | 1007358-19-1

• 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: 2-[1'-[(2-Methylpropan-2-yl)oxycarbonyl]-3-oxospiro[1,5-dihydro-2-benzazepine-4,2'-pyrrolidine]-2-yl]acetic acid
• CAS: 1007358-19-1
• 化学式: C₂₀H₂₆N₂O₅
• 分子量: 374.437
• InChiKey: QFRKTIRUKIKPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1'-[(2-Methylpropan-2-yl)oxycarbonyl]-3-oxospiro[1,5-dihydro-2-benzazepine-4,2'-pyrrolidine]-2-yl]acetic acid 、 丁氧羰基-O-2,6-二氯苄基-L-酪氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 、
  参考文献：
  名称：

  Endomorphin-2 with a β-Turn Backbone Constraint Retains the Potent μ-Opioid Receptor Agonist Properties

  摘要：

  The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 (1 and 2) and Tyr-(R/S)-Aba-Gly-Phe-NH2 (3 and 4). The (R)-spiro analog 1 was found to be a potent and selective mu-opioid agonist/partial agonist (K-i mu = 29.3 nM, IC50 = 50 nM, K-e = 0.57). NMR experiments and molecular modeling indicated that its backbone adopts mainly a U-turn in aqueous solution.

  DOI：

  10.1021/jm7010222
• 作为产物：
  描述：

  2-(3-Oxospiro[1,5-dihydro-2-benzazepine-4,2'-pyrrolidine]-2-yl)acetic acid 、 二碳酸二叔丁酯 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 生成 2-[1'-[(2-Methylpropan-2-yl)oxycarbonyl]-3-oxospiro[1,5-dihydro-2-benzazepine-4,2'-pyrrolidine]-2-yl]acetic acid
  参考文献：
  名称：

  Endomorphin-2 with a β-Turn Backbone Constraint Retains the Potent μ-Opioid Receptor Agonist Properties

  摘要：

  The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 (1 and 2) and Tyr-(R/S)-Aba-Gly-Phe-NH2 (3 and 4). The (R)-spiro analog 1 was found to be a potent and selective mu-opioid agonist/partial agonist (K-i mu = 29.3 nM, IC50 = 50 nM, K-e = 0.57). NMR experiments and molecular modeling indicated that its backbone adopts mainly a U-turn in aqueous solution.

  DOI：

  10.1021/jm7010222

文献信息

• Endomorphin-2 with a β-Turn Backbone Constraint Retains the Potent μ-Opioid Receptor Agonist Properties
  作者：Csaba Tömböly、Steven Ballet、Debby Feytens、Katalin E. Kövér、Attila Borics、Sándor Lovas、Mahmoud Al-Khrasani、Zsuzsanna Fürst、Géza Tóth、Sándor Benyhe、Dirk Tourwé

  DOI：10.1021/jm7010222

  日期：2008.1.1

  The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 (1 and 2) and Tyr-(R/S)-Aba-Gly-Phe-NH2 (3 and 4). The (R)-spiro analog 1 was found to be a potent and selective mu-opioid agonist/partial agonist (K-i mu = 29.3 nM, IC50 = 50 nM, K-e = 0.57). NMR experiments and molecular modeling indicated that its backbone adopts mainly a U-turn in aqueous solution.