Boc-Asp(OcHex)-Val-OBzl | 152020-28-5

• 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(OcHex)-Val-OBzl
• 英文别名: Boc-Asp(OcHx)-Val-OBzl
• CAS: 152020-28-5
• 化学式: C₂₇H₄₀N₂O₇
• 分子量: 504.624
• InChiKey: CVVBTPNDZJBGBS-GMAHTHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-Asp(OcHex)-Val-OBzl 生成 Boc-Gly-Asp(OcHex)-Val-OBzl
  参考文献：
  名称：

  Dual-acting agents that possess free radical scavenging and antithrombotic activities: Design, synthesis, and evaluation of phenolic tetrahydro-β-carboline RGD peptide conjugates

  摘要：

  A new approach to construct a single dual-acting agent is described. Compounds 6a-c are potent free radical scavengers as demonstrated by the EC50 values in PC12 cell survival assay in term of NO, H2O2, and (OH)-O-. scavenging activity. The Ach-induced vaso-relaxation assay further confirms the potent NO scavenging activity of compounds 6a-c. In addition, 6a-c are efficacious in a rat arterial thrombosis, and are active in ADP- or PAF-induced in vitro platelet aggregation assay, suggesting that compounds 6a-c also possess anti-thrombotic activities. Since both free radical and thrombogenesis are important risk factors in myocardial ischemic/reperfusion injuries, these dual-acting agents having both free radical scavenging and antithrombolic activities may potentially be beneficial toward their treatment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.024
• 作为产物：
  描述：

  ((S)-1-benzylcarbamoyl-2-methyl-propyl)-carbamic acid tert-butyl ester 生成 Boc-Asp(OcHex)-Val-OBzl
  参考文献：
  名称：

  Dual-acting agents that possess free radical scavenging and antithrombotic activities: Design, synthesis, and evaluation of phenolic tetrahydro-β-carboline RGD peptide conjugates

  摘要：

  A new approach to construct a single dual-acting agent is described. Compounds 6a-c are potent free radical scavengers as demonstrated by the EC50 values in PC12 cell survival assay in term of NO, H2O2, and (OH)-O-. scavenging activity. The Ach-induced vaso-relaxation assay further confirms the potent NO scavenging activity of compounds 6a-c. In addition, 6a-c are efficacious in a rat arterial thrombosis, and are active in ADP- or PAF-induced in vitro platelet aggregation assay, suggesting that compounds 6a-c also possess anti-thrombotic activities. Since both free radical and thrombogenesis are important risk factors in myocardial ischemic/reperfusion injuries, these dual-acting agents having both free radical scavenging and antithrombolic activities may potentially be beneficial toward their treatment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.024

文献信息

• Amino Acids and Peptides. XXIX. Synthesis and Antimetastatic Effects of Peptides and Peptide-Poly(Ethylene Glycol) Hybrids Related to the Core Sequence of the Type III Connecting Segment Domain of Fibronectin.
  作者：Koichi KAWASAKI、Mitsuko MAEDA、Sachiye INOUE、Yuko YAMASHIRO、Yoshihisa KANEDA、Yu MU、Yasuo TSUTSUMI、Shinsaku NAKAGAWA、Tadanori MAYUMI

  DOI：10.1248/bpb.19.1574

  日期：——

  Peptides (H-Glu-Ile-Leu-Asp-Val-NH2, H-Glu-Ile-Leu-Asp-Val-Pro-Ser-Thr-NH2, H-Arg-Glu-Asp-Val-NH2) and their poly(ethylene glycol)(PEG) hybrids related to the core sequence of the type III connecting segment domain of fibronectin A chain were prepared by the solution method or the solid phase method. Their inhibitory effects on the adhesion and migration of B16-BL6 melanoma cells to fibronectin were assessed in vitro, and their therapeutic potency against tumor metastasis were also examined. Anti-adhesive and anti-migrative effects of the synthetic fibronectin-related peptids were superior to those of their PEG hybrids, so we found that the in vitro bioactivity of peptides decreased by PEGylation. In the in vivo assay, we found that the synthetic peptides containing Glu-Ile-Leu-Asp-Val and Arg-Glu-Asp-Val sequences exhibited an inhibitory effect on the experimental metastasis of B16-BL6 melanoma. Of the synthetic peptides, H-Glu-Ile-Leu-Asp-Val-NH2 exhibited the most potent inhibitory effect. Hybrid formation of Arg-Glu-Asp-Val with poly(ethylene glycol) resulted in potentiation of the inhibitory effect of the parent peptides. A mixture composed of PEG hybrids of Glu-Ile-Leu-Asp-Val, Arg-Glu-Asp-Val and Tyr-Ile-Gly-Ser-Arg dramatically inhibited tumor metastasis.

  通过溶液法或固相法合成了包含纤连蛋白A链III型连接片段结构域核心序列的相关肽（H-Glu-Ile-Leu-Asp-Val-NH2、H-Glu-Ile-Leu-Asp-Val-Pro-Ser-Thr-NH2和H-Arg-Glu-Asp-Val-NH2）及其聚乙二醇（PEG）杂化物。在体外评估了它们对B16-BL6黑色素瘤细胞黏附和迁移至纤连蛋白的抑制效果，并检验了它们对抗肿瘤转移的治疗效力。合成纤连蛋白相关肽的抗黏附和抗迁移效果优于其PEG杂化物，因此我们发现，经PEG化修饰后，肽在体外的生物活性降低。在体内实验中，我们发现含有Glu-Ile-Leu-Asp-Val和Arg-Glu-Asp-Val序列的合成肽对B16-BL6黑色素瘤的实验性转移具有抑制作用。在所有合成肽中，H-Glu-Ile-Leu-Asp-Val-NH2显示出最强的抑制效果。将Arg-Glu-Asp-Val与聚乙二醇杂化后，增强了其母体肽的抑制效果。由Glu-Ile-Leu-Asp-Val、Arg-Glu-Asp-Val和Tyr-Ile-Gly-Ser-Arg的PEG杂化物组成的混合物显著抑制了肿瘤转移。
• Zhao, Ming; Peng, Shiqi, Advanced Synthesis and Catalysis, 1999, vol. 341, # 7, p. 668 - 676
  作者：Zhao, Ming、Peng, Shiqi

  DOI：——

  日期：——