BOC-D-Trp-ONP | 92608-63-4

• 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-D-Trp-ONP
• 英文别名: N-tBoc-D-tryptophan 4-nitrophenyl ester；(4-nitrophenyl) (2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 92608-63-4
• 化学式: C₂₂H₂₃N₃O₆
• 分子量: 425.441
• InChiKey: LQGKMKBNHAFRBV-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-D-Trp-ONP 在 N-乙基吗啉 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 BOC-D-Trp-Lys(MSC)-Thr-Phe-ONP
  参考文献：
  名称：

  Diaz; Cazaubon; Demarne, European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 219 - 227

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯酚 、 BOC-D-色氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以85%的产率得到BOC-D-Trp-ONP
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040

文献信息

• Phenethyl ester derivative analogs of the C-terminal tetrapeptide of gastrin as potent gastrin antagonists
  作者：Jean Martinez、Marc Rodriguez、Jean Pierre Bali、Jeanine Laur

  DOI：10.1021/jm00161a012

  日期：1986.11

  A series of phenethyl ester derivative analogues of the C-terminal tetrapeptide of gastrin, in which the phenylalanyl residue has been replaced by a phenethyl group and the peptide bond between aspartic acid and phenylalanine by an ester bond, were synthesized. None of these derivatives were able to stimulate gastric acid secretion in the anesthetized rat, whereas they inhibited gastrin-induced acid secretion with ED50 values between 0.02 and 1.5 mg/kg. Among these derivatives, Boc-beta Ala-Trp-Leu-Asp phenethyl ester (9) and Boc-beta Ala-Trp-Leu-Asp p-fluorophenethyl ester (16) were very potent in inhibiting gastrin-induced acid secretion. From these studies, the significant role of the C-terminal dipeptide of gastrin was pointed out. More particularly, the functional role of the phenylalanine through the C-terminal carboxamide and its binding role through its aromatic ring were demonstrated.