4-[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoic acid | 1025461-48-6

• 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: 4-[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoic acid
• CAS: 1025461-48-6
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: RTFSTQPHJANHKJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoic acid 、 (2-氨基-4-(噻吩-2-基)苯基)氨基甲酸叔丁酯 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Phenylglycine and phenylalanine derivatives as potent and selective HDAC1 inhibitors (SHI-1)

  摘要：

  An HTS screening campaign identified a series of low molecular weight phenols that showed excellent selectivity (> 100-fold) for HDAC1/HDAC2 over other Class I and Class II HDACs. Evolution and optimization of this HTS hit series provided HDAC1-selective (SHI-1) compounds with excellent anti-proliferative activity and improved physical properties. Dose-dependent efficacy in a mouse HCT116 xenograft model was demonstrated with a phenylglycine SHI-1 analog. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.012
• 作为产物：
  描述：

  (S)-4-(3-amino-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)phenyl triflate 、 一氧化碳 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到4-[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoic acid
  参考文献：
  名称：

  Suppression of racemization in the carbonylation of amino acid-derived aryl triflates

  摘要：

  The carbonylation of enantiopure phenylglycine-derived aryl triflates was achieved to afford 4-carboxyphenylglycine analogs with high enantiomeric excesses (88 to >99% ee). Amide analogs of phenylglycine were well-tolerated in the hydroxy- and methoxycarbonylation processes, providing efficient access to benzoic acid and ester building blocks. The % ee of the product was dependent on the relative steric bulk of both the amino acid substrate and the requisite amine base, with (Pr2NEt)-Pr-i proving optimal in minimizing product racemization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.145

文献信息

• Suppression of racemization in the carbonylation of amino acid-derived aryl triflates
  作者：Jonathan B. Grimm、Kevin J. Wilson、David J. Witter

  DOI：10.1016/j.tetlet.2007.04.145

  日期：2007.6

  The carbonylation of enantiopure phenylglycine-derived aryl triflates was achieved to afford 4-carboxyphenylglycine analogs with high enantiomeric excesses (88 to >99% ee). Amide analogs of phenylglycine were well-tolerated in the hydroxy- and methoxycarbonylation processes, providing efficient access to benzoic acid and ester building blocks. The % ee of the product was dependent on the relative steric bulk of both the amino acid substrate and the requisite amine base, with (Pr2NEt)-Pr-i proving optimal in minimizing product racemization. (c) 2007 Elsevier Ltd. All rights reserved.
• Phenylglycine and phenylalanine derivatives as potent and selective HDAC1 inhibitors (SHI-1)
  作者：Kevin J. Wilson、David J. Witter、Jonathan B. Grimm、Phieng Siliphaivanh、Karin M. Otte、Astrid M. Kral、Judith C. Fleming、Andreas Harsch、Julie E. Hamill、Jonathan C. Cruz、Melissa Chenard、Alexander A. Szewczak、Richard E. Middleton、Bethany L. Hughes、William K. Dahlberg、J. Paul Secrist、Thomas A. Miller

  DOI：10.1016/j.bmcl.2008.02.012

  日期：2008.3

  An HTS screening campaign identified a series of low molecular weight phenols that showed excellent selectivity (> 100-fold) for HDAC1/HDAC2 over other Class I and Class II HDACs. Evolution and optimization of this HTS hit series provided HDAC1-selective (SHI-1) compounds with excellent anti-proliferative activity and improved physical properties. Dose-dependent efficacy in a mouse HCT116 xenograft model was demonstrated with a phenylglycine SHI-1 analog. (C) 2008 Elsevier Ltd. All rights reserved.