(6R,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one methyl ester | 1004984-22-8

• 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: (6R,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one methyl ester
• 英文别名: methyl (6S,8aR)-6-[[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]amino]-6-(2-methylpropyl)-5-oxo-2,3,7,8-tetrahydro-1H-indolizine-8a-carboxylate
• CAS: 1004984-22-8
• 化学式: C₂₄H₃₉N₃O₆
• 分子量: 465.59
• InChiKey: XHLWDPNOHFLQOD-YRUKQIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6R,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one methyl ester 在 六甲基磷酰三胺 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (6S,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one
  参考文献：
  名称：

  Allosteric Modulation of the Dopamine Receptor by Conformationally Constrained Type VI β-Turn Peptidomimetics of Pro-Leu-Gly-NH₂

  摘要：

  A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI beta-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of a-allylproline. Bicyclic peptidomimetic 7 and spirobicylic peptidomimetic 8 enhanced the binding of [H-3]N-propylnorapomorphine to dopamine receptors indicating that a type VI beta-turn is a possible bioactive conformation of the homochiral Pro-Leu-Pro-NH2 and Pro-Pro-Pro-NH2 analogues of Pro-Leu-Gly-NH2 at the dopamine receptor allosteric regulatory site.

  DOI：

  10.1021/jm070895r
• 作为产物：
  描述：

  (6R,8aR)-6-amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one methyl ester trifluoroacetate 、 BOC-L-脯氨酸 在 N-甲基吗啉 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到(6R,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one methyl ester
  参考文献：
  名称：

  Allosteric Modulation of the Dopamine Receptor by Conformationally Constrained Type VI β-Turn Peptidomimetics of Pro-Leu-Gly-NH₂

  摘要：

  A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI beta-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of a-allylproline. Bicyclic peptidomimetic 7 and spirobicylic peptidomimetic 8 enhanced the binding of [H-3]N-propylnorapomorphine to dopamine receptors indicating that a type VI beta-turn is a possible bioactive conformation of the homochiral Pro-Leu-Pro-NH2 and Pro-Pro-Pro-NH2 analogues of Pro-Leu-Gly-NH2 at the dopamine receptor allosteric regulatory site.

  DOI：

  10.1021/jm070895r