3-[[[(2S)-2-[[(3S,4S)-4-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]hexanoyl]amino]methyl]benzoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 3-[[[(2S)-2-[[(3S,4S)-4-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]hexanoyl]amino]methyl]benzoic acid
• 化学式: C₃₅H₅₇N₅O₈S
• 分子量: 707.932
• InChiKey: YZBDIFXFTYWUEW-XMMDVVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  49
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  228
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酸酐 、 Fmoc-L-蛋氨酸 、 芴甲氧羰酰基正亮氨酸 、 (3S,4S)-4-[(芴甲氧羰基)氨基]-3-羟基-6-甲基庚酸 、 3-(Fmoc-氨甲基)苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3-[[[(2S)-2-[[(3S,4S)-4-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxy-6-methylheptanoyl]amino]hexanoyl]amino]methyl]benzoic acid
  参考文献：
  名称：

  Design and synthesis of statine-Containing BACE inhibitors

  摘要：

  Utilizing structure-based techniques and solid-phase synthesis, statine-based tetrapeptide BACE inhibitors were designed and synthesized using a heptapeptide BACE transition-state mimetic, 1, as the starting point. Structure-activity relationship studies at the P-3, P-2, and P-2' positions as well as the N-terminal capping group on scaffold 5 led to the discovery of potent inhibitors 27, 32, and 34 (IC50 < 100 nM). In addition, computational analysis and the X-ray structure of BACE-inhibitor 38 are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.037

文献信息

• Design and synthesis of statine-Containing BACE inhibitors
  作者：Jingdan Hu、Cynthia L Cwi、David L Smiley、David Timm、Jon A Erickson、James E McGee、Hsiu-Chiung Yang、David Mendel、Patrick C May、Mike Shapiro、James R McCarthy

  DOI：10.1016/j.bmcl.2003.09.037

  日期：2003.12

  Utilizing structure-based techniques and solid-phase synthesis, statine-based tetrapeptide BACE inhibitors were designed and synthesized using a heptapeptide BACE transition-state mimetic, 1, as the starting point. Structure-activity relationship studies at the P-3, P-2, and P-2' positions as well as the N-terminal capping group on scaffold 5 led to the discovery of potent inhibitors 27, 32, and 34 (IC50 < 100 nM). In addition, computational analysis and the X-ray structure of BACE-inhibitor 38 are discussed. (C) 2003 Elsevier Ltd. All rights reserved.