(R)-4-benzyl-3-pent-2-enoyl-oxazolidin-2-one | 1054529-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-benzyl-3-pent-2-enoyl-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-pent-2-enoyl-1,3-oxazolidin-2-one
• CAS: 1054529-60-0
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: PPMFEJKQNMXSEY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-pent-2-enoyl-oxazolidin-2-one 、 ISOBUTYLMAGNESIUM BROMIDE 在 copper(I) bromide dimethylsulfide complex 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 二甲基硫 为溶剂， 生成 C₁₉H₂₆BrNO₃
  参考文献：
  名称：

  (S)-N-(5-Chlorothiophene-2-sulfonyl)-β,β-diethylalaninol a Notch-1-sparing γ-secretase inhibitor

  摘要：

  Accumulation of beta-amyloid (A beta), produced by the proteolytic cleavage of amyloid precursor protein (APP) by beta- and gamma-secretase, is widely believed to be associated with Alzheimer's disease (AD). Research around the high-throughput screening hit (S)-4-chlorophenylsulfonyl isoleucinol led to the identification of the Notch-1-sparing (9.5-fold) gamma-secretase inhibitor (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol 7.b.2 (A beta (40/42) EC50 = 28 nM), which is efficacious in reduction of A beta production in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.116
• 作为产物：
  描述：

  2-戊烯酸 、 (R)-4-苄基-2-噁唑烷酮 在 三甲基乙酰氯 、 三乙胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-benzyl-3-pent-2-enoyl-oxazolidin-2-one
  参考文献：
  名称：

  (S)-N-(5-Chlorothiophene-2-sulfonyl)-β,β-diethylalaninol a Notch-1-sparing γ-secretase inhibitor

  摘要：

  Accumulation of beta-amyloid (A beta), produced by the proteolytic cleavage of amyloid precursor protein (APP) by beta- and gamma-secretase, is widely believed to be associated with Alzheimer's disease (AD). Research around the high-throughput screening hit (S)-4-chlorophenylsulfonyl isoleucinol led to the identification of the Notch-1-sparing (9.5-fold) gamma-secretase inhibitor (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol 7.b.2 (A beta (40/42) EC50 = 28 nM), which is efficacious in reduction of A beta production in vivo. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.116

文献信息

• Discovery of a novel series of Notch-sparing γ-secretase inhibitors
  作者：Anthony Kreft、Boyd Harrison、Suzan Aschmies、Kevin Atchison、David Casebier、Derek C. Cole、George Diamantidis、John Ellingboe、Diane Hauze、Yun Hu、Donna Huryn、Mei Jin、Dennis Kubrak、Peimin Lu、Joseph Lundquist、Charles Mann、Robert Martone、William Moore、Aram Oganesian、Alex Porte、Dave R. Riddell、June Sonnenberg-Reines、Joseph R. Stock、Shaiu-Ching Sun、Erik Wagner、Kevin Woller、Zheng Xu、Hua Zhou、J. Steven Jacobsen

  DOI：10.1016/j.bmcl.2008.05.064

  日期：2008.7

  Using a cell-based assay, we have identified a new series of Notch-sparing gamma-secretase inhibitors from HTS screening leads 2a and 2e. Lead optimization studies led to the discovery of analog 8e with improved gamma-secretase inhibitory potency and Notch-sparing selectivity. (C) 2008 Elsevier Ltd. All rights reserved.