Boc-Asp(NHBzl)-OBzl | 150210-89-2

• 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: Boc-Asp(NHBzl)-OBzl
• CAS: 150210-89-2
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: WWCIOYGHJPYUNT-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Asp(NHBzl)-OBzl 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-Amino-1-benzyl-pyrrolidine-2,5-dione; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Efficient synthesis of N-benzyl-3-aminopyrrolidine-2,5-dione and N-benzyl-3-aminopyrrolidin-2-one

  摘要：

  Reaction of N-tert-butyloxycarbonylasparagine (Boc-Asn) with 2 equiv of benzyl bromide in presence of cesium carbonate led to N-benzyl-3-Boc-amino-pyrrolidin-2,5-dione 1a (N-benzyl-3-Boc-aminosuccinimide). Borane dimethylsulfide reduced 3-Boc-aminopyrrolidine-2,5-dione 1a into 3-Boc-aminopyrrolidin-2-one 2a. The same procedure could also be used to prepare derivatives 1 and 2 substituted on the aromatic ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.052
• 作为产物：
  描述：

  Boc-L-天冬氨酸 1-苄酯 、 苄胺 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以70%的产率得到Boc-Asp(NHBzl)-OBzl
  参考文献：
  名称：

  Influence of Lipophilicity on the Biological Activity of Cyclic Pseudopeptide NK-2 Receptor Antagonists

  摘要：

  A series of cyclic pseudopeptides of the formula cyclo(Leu Psi[CH2NH]Xaa-Gln-Trp-Phe-beta Ala), where Xaa represents the residue of an alpha-amino acid, has been synthesized in order to establish the role of the Xaa side chain for tachykinin NK-2 receptor antagonist activity. Syntheses have been carried out in solid phase with either Fmoc or Boc strategy. The antagonist potency on NK-2 receptors in the hamster isolated trachea (HT) and the rabbit isolated pulmonary artery (RPA) bioassays increases with Xaa Lipophilicity; cyclo(Leu Psi[CH2NH]Cha-Gln-Trp-Phe-beta Ala) and cyclo(Leu Psi[CH2NH]Asp(NHBzl)-Gln-Trp-beta Ala) resulted in being the two most active antagonists (pA(2) = 9.06 and 9.26 on HT, respectively). A significant linear correlation was found between pA(2) values determined in HT and RPA bioassays and capacity factors measured in reversed phase HPLC. The comparison between the biological activities of cyclic hexapeptides containing or not containing the aminomethylene moiety proved the crucial role of the pseudopeptide bond for determining high antagonist potency at the NK-2 receptor.

  DOI：

  10.1021/jm00047a020