(6S,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one | 1004984-23-9

• 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: (6S,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one
• 英文别名: (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-carboxylic acid
• CAS: 1004984-23-9
• 化学式: C₂₃H₃₇N₃O₆
• 分子量: 451.563
• InChiKey: UYMUSNATBHLDTL-IRBZQWRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6S,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxyindolizidin-5-one 在 氨 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以430 mg的产率得到(6S,8aR,2'S)-6-N-(tert-butoxycarbonyl-2'-pyrrolidinylcarbonyl)amino-6-(2-methylpropyl)-8a-carboxamidoindolizidin-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,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

文献信息

• Allosteric Modulation of the Dopamine Receptor by Conformationally Constrained Type VI β-Turn Peptidomimetics of Pro-Leu-Gly-NH₂
  作者：Ashish P. Vartak、Kevin Skoblenick、Nancy Thomas、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm070895r

  日期：2007.12.27

  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.