benzyl 3-[[1-[(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]piperidine-3-carbonyl]amino]propanoate | 173299-67-7

• 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: benzyl 3-[[1-[(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]piperidine-3-carbonyl]amino]propanoate
• CAS: 173299-67-7
• 化学式: C₂₉H₄₄N₄O₇
• 分子量: 560.691
• InChiKey: FPZKRXDNSRKIBA-CGAIIQECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3-[[1-[(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]piperidine-3-carbonyl]amino]propanoate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 3-{[1-((S)-2-Acetylamino-6-tert-butoxycarbonylamino-hexanoyl)-piperidine-3-carbonyl]-amino}-propionic acid; compound with acetic 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：

  β-丙氨酸苄酯对甲苯磺酸盐 、 Ac-L-Lys(Boc)-Nip-OH 在 N-甲基吗啉 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 benzyl 3-[[1-[(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]piperidine-3-carbonyl]amino]propanoate
  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