(2S)-2-[((2R*,5S*,7S*,8aR*)-2-(3-guanidino-propyl)-7-hydroxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid | 1131844-06-8

• 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: (2S)-2-[((2R*,5S*,7S*,8aR*)-2-(3-guanidino-propyl)-7-hydroxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid
• 英文别名: (2S)-2-[[2-[3-(diaminomethylideneamino)propyl]-7-hydroxy-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizine-5-carbonyl]amino]pentanedioic acid
• CAS: 1131844-06-8
• 化学式: C₁₈H₂₉N₅O₇
• 分子量: 427.458
• InChiKey: QZHNPTFNTPMOAS-RFMXUXEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  209
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S)-2-[((2R*,5S*,7S*,8aR*)-2-(3-bis(tert-butyloxycarbonyl)guanidino-propyl)-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以100%的产率得到(2S)-2-[((2R*,5S*,7S*,8aR*)-2-(3-guanidino-propyl)-7-hydroxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid
  参考文献：
  名称：

  Synthesis and evaluation of substituted indolizidines as peptidomimetics of RGD tripeptide sequence

  摘要：

  The synthesis of seven peptidomimetics of RGD is presented. The indolizidine building block was obtained by condensation of allylglycine with dimethoxydihydrofuran followed by an intermolecular cyclization. The bicyclic ring was functionalised with a carboxylic acid and a guanidinium appendage. The seven peptidomimetics were evaluated by cell-adhesion assays. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.015

文献信息

• Synthesis and evaluation of substituted indolizidines as peptidomimetics of RGD tripeptide sequence
  作者：Delphine Halie、Joëlle Pérard-Viret、Sylvie Dufour、Jacques Royer

  DOI：10.1016/j.tet.2008.12.015

  日期：2009.2

  The synthesis of seven peptidomimetics of RGD is presented. The indolizidine building block was obtained by condensation of allylglycine with dimethoxydihydrofuran followed by an intermolecular cyclization. The bicyclic ring was functionalised with a carboxylic acid and a guanidinium appendage. The seven peptidomimetics were evaluated by cell-adhesion assays. (C) 2008 Elsevier Ltd. All rights reserved.