1-(6-Boc-aminocaproyl)piperidine-3-carboxaldehyde | 173051-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(6-Boc-aminocaproyl)piperidine-3-carboxaldehyde
• 英文别名: tert-butyl N-[6-(3-formylpiperidin-1-yl)-6-oxohexyl]carbamate
• CAS: 173051-69-9
• 化学式: C₁₇H₃₀N₂O₄
• 分子量: 326.436
• InChiKey: IMWMLELLPAIFFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-Boc-aminocaproyl)piperidine-3-carboxaldehyde 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 44.5h， 生成 3-{[1-(6-Amino-hexanoyl)-piperidin-3-ylmethyl]-amino}-propionic acid
  参考文献：
  名称：

  Design and Evaluation of Nonpeptide Fibrinogen .gamma. Chain-Based GPIIB/IIIA Antagonists

  摘要：

  Two series of nonpeptide turn mimetics were designed by analysis of the solution NMR structure of the 385-411 sequence of the gamma-chain of fibrinogen. These compounds, based on the KQAGD (Lys-Gln-Ala-Gly-Asp, 406-410) sequence, were synthesized and studied in vitro. The most interesting compound from our study, RWJ 50042 (25), exhibits potent inhibition of fibrinogen binding to GPIIb/IIIa (IC50 = 0.009 mu M), as well as thrombin- or collagen-induced platelet aggregation (IC50 = 0.76, 0.14 mu M). Since the 400-411 sequence is required for gamma-chain bioactivity and is a unique recognition sequence among ligands for integrins, vis-a-vis other RGD (Arg-Gly-Asp)-presenting proteins, these turn mimetics may represent a new, selective approach to antagonism of the fibrinogen receptor.

  DOI：

  10.1021/jm00010a002
• 作为产物：
  描述：

  Boc 氨基已酸-Osu 在 N-甲基吗啉 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 二异丁基氢化铝 、 N,N'-羰基二咪唑 作用下， 反应 5.5h， 生成 1-(6-Boc-aminocaproyl)piperidine-3-carboxaldehyde
  参考文献：
  名称：

  Design and Evaluation of Nonpeptide Fibrinogen .gamma. Chain-Based GPIIB/IIIA Antagonists

  摘要：

  Two series of nonpeptide turn mimetics were designed by analysis of the solution NMR structure of the 385-411 sequence of the gamma-chain of fibrinogen. These compounds, based on the KQAGD (Lys-Gln-Ala-Gly-Asp, 406-410) sequence, were synthesized and studied in vitro. The most interesting compound from our study, RWJ 50042 (25), exhibits potent inhibition of fibrinogen binding to GPIIb/IIIa (IC50 = 0.009 mu M), as well as thrombin- or collagen-induced platelet aggregation (IC50 = 0.76, 0.14 mu M). Since the 400-411 sequence is required for gamma-chain bioactivity and is a unique recognition sequence among ligands for integrins, vis-a-vis other RGD (Arg-Gly-Asp)-presenting proteins, these turn mimetics may represent a new, selective approach to antagonism of the fibrinogen receptor.

  DOI：

  10.1021/jm00010a002

文献信息

• Design and Evaluation of Nonpeptide Fibrinogen .gamma. Chain-Based GPIIB/IIIA Antagonists
  作者：William J. Hoekstra、Mary Pat Beavers、Patricia Andrade-Gordon、Mary F. Evangelisto、Patricia M. Keane、Jeffery B. Press、Karen A. Tomko、Francis Fan、Marek Kloczewiak

  DOI：10.1021/jm00010a002

  日期：1995.5

  Two series of nonpeptide turn mimetics were designed by analysis of the solution NMR structure of the 385-411 sequence of the gamma-chain of fibrinogen. These compounds, based on the KQAGD (Lys-Gln-Ala-Gly-Asp, 406-410) sequence, were synthesized and studied in vitro. The most interesting compound from our study, RWJ 50042 (25), exhibits potent inhibition of fibrinogen binding to GPIIb/IIIa (IC50 = 0.009 mu M), as well as thrombin- or collagen-induced platelet aggregation (IC50 = 0.76, 0.14 mu M). Since the 400-411 sequence is required for gamma-chain bioactivity and is a unique recognition sequence among ligands for integrins, vis-a-vis other RGD (Arg-Gly-Asp)-presenting proteins, these turn mimetics may represent a new, selective approach to antagonism of the fibrinogen receptor.