4-[N-(t-butoxycarbonyl)-isoindoline-5-yl]amino-4-oxobutyric acid | 807627-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-[N-(t-butoxycarbonyl)-isoindoline-5-yl]amino-4-oxobutyric acid
• 英文别名: 4-(N-Boc-isoindolin-5-yl)amino-4-oxobutanoic acid；5-(3-Carboxy-propionylamino)-1,3-dihydro-isoindole-2-carboxylic acid, tert-butyl ester；4-[[2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-dihydroisoindol-5-yl]amino]-4-oxobutanoic acid
• CAS: 807627-82-3
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: LUZGYKFEAJVSKP-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C
• 沸点：
  563.5±50.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[N-(t-butoxycarbonyl)-isoindoline-5-yl]amino-4-oxobutyric acid 在 盐酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[4-(isoindolin-5-yl)amino-4-oxobutyryl]-D,L-β-(p-methoxyphenyl)-β-alanine hydrochloride
  参考文献：
  名称：

  4-(Isoindolin-5-yl)amino-4-oxobutyryl-β-alkoxyphenyl-β-alanines, new RGDF mimetics. Synthesis, affinity to fibrinogen receptors, antiaggregatory properties, and their correlation with the hydrophobicity

  摘要：

  A new series of RGDF mimetics, derivatives of 4-(isoindolin-5-yl)amino-4-oxobutanoic acid, was synthesized. The compounds obtained inhibit efficiently the thrombocytes aggregation in experiments in vitro; their biological targets are fibrinogen receptors. The antiaggregatory activity and the affinity correlate with the hydrophobicity of the compounds.

  DOI：

  10.1134/s1070428006080124
• 作为产物：
  描述：

  N-叔丁氧羰基-5-氨基异吲哚啉 在 palladium on activated charcoal 一水合肼 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 0.5h， 生成 4-[N-(t-butoxycarbonyl)-isoindoline-5-yl]amino-4-oxobutyric acid
  参考文献：
  名称：

  4-(Isoindolin-5-yl)amino-4-oxobutyryl-β-alkoxyphenyl-β-alanines, new RGDF mimetics. Synthesis, affinity to fibrinogen receptors, antiaggregatory properties, and their correlation with the hydrophobicity

  摘要：

  A new series of RGDF mimetics, derivatives of 4-(isoindolin-5-yl)amino-4-oxobutanoic acid, was synthesized. The compounds obtained inhibit efficiently the thrombocytes aggregation in experiments in vitro; their biological targets are fibrinogen receptors. The antiaggregatory activity and the affinity correlate with the hydrophobicity of the compounds.

  DOI：

  10.1134/s1070428006080124

文献信息

• Novel fibrinogen receptor antagonists. RGDF mimetics, derivatives of 4-(isoindoline-5-yl)amino-4-oxobutyric acid
  作者：Andrei A. Krysko、Boris M. Chugunov、Olga L. Malovichko、Sergei A. Andronati、Tatyana A. Kabanova、Tamara L. Karaseva、Anna V. Kiriyak

  DOI：10.1016/j.bmcl.2004.09.002

  日期：2004.11

  The novel RGDF mimetics 9a and 9b were synthesized with the use of 4-(isoindoline-5-yl)amino-4-oxo butyric acid as a surrogate of Arg-Gly motif. The synthesized compounds have demonstrated a high potency to inhibit platelet aggregation in vitro and to block FITC-Fg binding to alpha(IIb)beta(3) on washed human platelets. (C) 2004 Elsevier Ltd. All rights reserved.
• 4-(Isoindolin-5-yl)amino-4-oxobutyryl-β-alkoxyphenyl-β-alanines, new RGDF mimetics. Synthesis, affinity to fibrinogen receptors, antiaggregatory properties, and their correlation with the hydrophobicity
  作者：S. A. Andronati、A. A. Krys’ko、B. M. Chugunov、T. A. Kabanova、A. G. Artemenko

  DOI：10.1134/s1070428006080124

  日期：2006.8

  A new series of RGDF mimetics, derivatives of 4-(isoindolin-5-yl)amino-4-oxobutanoic acid, was synthesized. The compounds obtained inhibit efficiently the thrombocytes aggregation in experiments in vitro; their biological targets are fibrinogen receptors. The antiaggregatory activity and the affinity correlate with the hydrophobicity of the compounds.