<<<1-(6-Boc-aminocaproyl)piperid-3-yl>methyl>amino>propionic acid benzyl ester | 173051-70-2

• 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: <<<1-(6-Boc-aminocaproyl)piperid-3-yl>methyl>amino>propionic acid benzyl ester
• 英文别名: Benzyl 3-[[1-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]piperidin-3-yl]methylamino]propanoate
• CAS: 173051-70-2
• 化学式: C₂₇H₄₃N₃O₅
• 分子量: 489.656
• InChiKey: BSCIRLLOGOYGPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <<<1-(6-Boc-aminocaproyl)piperid-3-yl>methyl>amino>propionic acid benzyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 3-{[1-(6-Amino-hexanoyl)-piperidin-3-ylmethyl]-amino}-propionic acid benzyl ester
  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 、 sodium cyanoborohydride 、 N,N'-羰基二咪唑 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 <<<1-(6-Boc-aminocaproyl)piperid-3-yl>methyl>amino>propionic acid benzyl ester
  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.