{(S)-1-[(2S,14S)-2-(4-Hydroxy-benzyl)-3,8,15-trioxo-1,4,9-triaza-cyclopentadec-14-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester | 1028285-37-1

• 英文名称: {(S)-1-[(2S,14S)-2-(4-Hydroxy-benzyl)-3,8,15-trioxo-1,4,9-triaza-cyclopentadec-14-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S,14S)-2-[(4-hydroxyphenyl)methyl]-3,8,15-trioxo-1,4,9-triazacyclopentadec-14-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 1028285-37-1
• 化学式: C₄₃H₄₇N₅O₇
• 分子量: 745.875
• InChiKey: MLNWYDSWONRVDZ-QXUSSCGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(2S,14S)-2-(4-Hydroxy-benzyl)-3,8,15-trioxo-1,4,9-triaza-cyclopentadec-14-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 H-Phe-c[-N^ε-Lys-Tyr-Abu-]
  参考文献：
  名称：

  Design and Synthesis of Motilin Antagonists Derived from the [1−4] Fragment of Porcine Motilin

  摘要：

  A series of cyclic peptides having the general structure H-Phe-c[-N-epsilon-Lys-X-NH-(CH2)(n)-CO-] were designed on the basis of structure-activity relationship studies of motilin. All were motilin antagonists. The cyclic peptides, in which X is a 3-tert-butyl-substituted tyrosine residue (H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-betaAla-] (3), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Gly-] (6), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Abu-] (7), and H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Ahx-] (8)) showed potent motilin receptor antagonistic activity in the rabbit smooth muscle (pA(2) > 7). The 3-tert-butyl Tyr was found to be the moiety responsible for enhanced binding to the motilin receptor, while the size of the ring had little importance.

  DOI：

  10.1021/jm010332u
• 作为产物：
  描述：

  4-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]butanoic acid 在 吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 {(S)-1-[(2S,14S)-2-(4-Hydroxy-benzyl)-3,8,15-trioxo-1,4,9-triaza-cyclopentadec-14-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Design and Synthesis of Motilin Antagonists Derived from the [1−4] Fragment of Porcine Motilin

  摘要：

  A series of cyclic peptides having the general structure H-Phe-c[-N-epsilon-Lys-X-NH-(CH2)(n)-CO-] were designed on the basis of structure-activity relationship studies of motilin. All were motilin antagonists. The cyclic peptides, in which X is a 3-tert-butyl-substituted tyrosine residue (H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-betaAla-] (3), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Gly-] (6), H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Abu-] (7), and H-Phe-c[-N-epsilon-Lys-Tyr(3-tBu)-Ahx-] (8)) showed potent motilin receptor antagonistic activity in the rabbit smooth muscle (pA(2) > 7). The 3-tert-butyl Tyr was found to be the moiety responsible for enhanced binding to the motilin receptor, while the size of the ring had little importance.

  DOI：

  10.1021/jm010332u