(2R)-2-[4-(苄氧基)苄基]-4-叔丁氧基-4-氧代丁酸 | 377088-75-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (2R)-2-[4-(苄氧基)苄基]-4-叔丁氧基-4-氧代丁酸
• 英文名称: (2R)-2-[4-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid
• 英文别名: (2R)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-[(4-phenylmethoxyphenyl)methyl]butanoic acid
• CAS: 377088-75-0
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: XEVSMSHYBWUANZ-GOSISDBHSA-N

物化性质

• 沸点：
  529.7±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-[4-(苄氧基)苄基]-4-叔丁氧基-4-氧代丁酸 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  Nonpeptidic SH2 inhibitors of the tyrosine kinase ZAP-70

  摘要：

  The synthesis of a series of 1,2,4-oxadiazole analogs is discussed along with their ZAP-70 SH2 inhibitory activity. The tyrosine moiety in the original series has been replaced with nonpeptidic functional groups without a substantial loss of binding affinity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00524-7
• 作为产物：
  描述：

  3-[4-(苄氧基)苯基]丙酸 在 lithium hydroxide 、 正丁基锂 、 双氧水 、 三甲基乙酰氯 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 (2R)-2-[4-(苄氧基)苄基]-4-叔丁氧基-4-氧代丁酸
  参考文献：
  名称：

  Discovery of Macrocyclic Hydroxamic Acids Containing Biphenylmethyl Derivatives at P1‘, a Series of Selective TNF-α Converting Enzyme Inhibitors with Potent Cellular Activity in the Inhibition of TNF-α Release

  摘要：

  SAR exploration at P1' using an anti-succinate-based macrocyclic hydroxamic acid as a template led to the identification of several bulky biphenylmethyl P1' derivatives which confer potent porcine TACE and anti-TNF-alpha cellular activities with high selectivity versus most of the MMPs screened. Our studies demonstrate for the first time that TACE has a larger S1' pocket in comparison to MMPs and that potent and selective TACE inhibitors can be achieved by incorporation of sterically bulky P1' residues.

  DOI：

  10.1021/jm0155502

文献信息

• Discovery of Macrocyclic Hydroxamic Acids Containing Biphenylmethyl Derivatives at P1‘, a Series of Selective TNF-α Converting Enzyme Inhibitors with Potent Cellular Activity in the Inhibition of TNF-α Release
  作者：Chu-Biao Xue、Xiaohua He、Ronald L. Corbett、John Roderick、Zelda R. Wasserman、Rui-Qin Liu、Bruce D. Jaffee、Maryanne B. Covington、Mingxin Qian、James M. Trzaskos、Robert C. Newton、Ronald L. Magolda、Ruth R. Wexler、Carl P. Decicco

  DOI：10.1021/jm0155502

  日期：2001.10.1

  SAR exploration at P1' using an anti-succinate-based macrocyclic hydroxamic acid as a template led to the identification of several bulky biphenylmethyl P1' derivatives which confer potent porcine TACE and anti-TNF-alpha cellular activities with high selectivity versus most of the MMPs screened. Our studies demonstrate for the first time that TACE has a larger S1' pocket in comparison to MMPs and that potent and selective TACE inhibitors can be achieved by incorporation of sterically bulky P1' residues.
• Nonpeptidic SH2 inhibitors of the tyrosine kinase ZAP-70
  作者：Chi B. Vu、Evelyn G. Corpuz、Selvaluxmi G. Pradeepan、Shelia Violette、Catherine Bartlett、Tomi K. Sawyer

  DOI：10.1016/s0960-894x(99)00524-7

  日期：1999.10

  The synthesis of a series of 1,2,4-oxadiazole analogs is discussed along with their ZAP-70 SH2 inhibitory activity. The tyrosine moiety in the original series has been replaced with nonpeptidic functional groups without a substantial loss of binding affinity. (C) 1999 Elsevier Science Ltd. All rights reserved.