Boc-LeuΨCha-OBzl | 160908-85-0

• 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-LeuΨCha-OBzl
• 英文别名: benzyl (2S)-3-cyclohexyl-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]amino]propanoate
• CAS: 160908-85-0
• 化学式: C₂₇H₄₄N₂O₄
• 分子量: 460.657
• InChiKey: JONSJEZUTRLKCS-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-LeuΨCha-OBzl 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 Boc-LeuΨCha-OH
  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
• 作为产物：
  描述：

  叔丁氧羰酰基Β环己基丙氨酸二环己胺盐 在 4-二甲氨基吡啶 、 potassium hydrogensulfate 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 Boc-LeuΨCha-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

文献信息

• Influence of Lipophilicity on the Biological Activity of Cyclic Pseudopeptide NK-2 Receptor Antagonists
  作者：Laura Quartara、Gaetano Fabbri、Renzo Ricci、Riccardo Patacchini、Vittorio Pestellini、Carlo Alberto Maggi、Vincenzo Pavone、Antonio Giachetti、Federico Arcamone

  DOI：10.1021/jm00047a020

  日期：1994.10

  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.