(2S)-2-[[(2S)-2-fluoro-3-methylbutanoyl]amino]propanoic acid | 669074-39-9

• 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: (2S)-2-[[(2S)-2-fluoro-3-methylbutanoyl]amino]propanoic acid
• CAS: 669074-39-9
• 化学式: C₈H₁₄FNO₃
• 分子量: 191.202
• InChiKey: FYLSLQSRMWAYTL-WDSKDSINSA-N

物化性质

• 沸点：
  371.2±27.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S)-2-fluoro-3-methylbutanoyl]amino]propanoic acid 、 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到(2R,4S,5S)-5-[[(2S)-2-[[(2S)-2-fluoro-3-methylbutanoyl]amino]propanoyl]amino]-4-hydroxy-2-methyl-N-[(2S)-3-methyl-1-oxo-1-(pyridin-4-ylmethylamino)butan-2-yl]-6-phenylhexanamide
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085
• 作为产物：
  描述：

  (S)-3-(3-甲基丁酰基)-4-苄基-2-恶唑烷酮 在 盐酸 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 双氧水 、 N-氟代双苯磺酰胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-[[(2S)-2-fluoro-3-methylbutanoyl]amino]propanoic acid
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085

文献信息

• P3 cap modified Phe*-Ala series BACE inhibitors
  作者：Shu-Hui Chen、Jason Lamar、Deqi Guo、Todd Kohn、Hsiu-Chiung Yang、James McGee、David Timm、Jon Erickson、Yvonne Yip、Patrick May、James McCarthy

  DOI：10.1016/j.bmcl.2003.09.085

  日期：2004.1

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.