(2S)-2-[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumyl-3-(4-hydroxyphenyl)-N-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenyl]propanimidate | 728916-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumyl-3-(4-hydroxyphenyl)-N-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenyl]propanimidate
• CAS: 728916-17-4
• 化学式: C₂₈H₂₉N₃O₉
• 分子量: 551.553
• InChiKey: VVCGOKCJYZRQDL-DEOSSOPVSA-N

物化性质

• 熔点：
  175-179 °C
• 沸点：
  804.6±65.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-2-[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumyl-3-(4-hydroxyphenyl)-N-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenyl]propanimidate 在 四氯化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Towards enzyme activated antiprostatic agents

  摘要：

  A prodrug conjugate designed to undergo activation by enzymatic prostate specific antigen has been synthesized, The prodrug system undergoes activation with PSA or alpha-chymotrypsin, and shows selective cytotoxicity in a PSA secreting cell line. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00386-3
• 作为产物：
  描述：

  对氨基苯甲醇 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (2S)-2-[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]azaniumyl-3-(4-hydroxyphenyl)-N-[4-[(4-nitrophenoxy)carbonyloxymethyl]phenyl]propanimidate
  参考文献：
  名称：

  Image contrast agents activated by prostate specific antigen (PSA)

  摘要：

  A family of image contrast agent conjugates designed to undergo enzymatic activation has been synthesized. The agents underwent activation both with enzymatically active prostate specific antigen and alpha-chymotrypsin, releasing free fluorophore via cleavage of a three-component system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.041

文献信息

• A Strategy for the Selective Imaging of Glycans Using Caged Metabolic Precursors
  作者：Pamela V. Chang、Danielle H. Dube、Ellen M. Sletten、Carolyn R. Bertozzi

  DOI：10.1021/ja101080y

  日期：2010.7.21

  Glycans can be imaged by metabolic labeling with azidosugars followed by chemical reaction with imaging probes; however, tissue-specific labeling is difficult to achieve. Here we describe a strategy for the use of a caged metabolic precursor that is activated for cellular metabolism by enzymatic cleavage. An N-azidoacetylmannosamine derivative caged with a peptide substrate for the prostate-specific antigen (PSA) protease was converted to cell-surface azido sialic acids in a PSA-dependent manner. The approach has applications in tissue-selective imaging of glycans for clinical and basic research purposes.
• An image contrast agent selectively activated by prostate specific antigen
  作者：Graham B. Jones、Curtis F. Crasto、Jude E. Mathews、Longfei Xie、Miguel O. Mitchell、Ahmed El-Shafey、Anthony V. D’Amico、Glenn J. Bubley

  DOI：10.1016/j.bmc.2005.08.015

  日期：2006.1

  A family of image contrast agent conjugates designed to undergo enzymatic activation has been synthesized. The agents underwent activation both with enzymatically active prostate specific antigen (PSA) and a-chymotrypsin, releasing free fluorophore via cleavage of a three-component system. A hexapeptide derivative showed exclusive activation by PSA and constitutes a method for tracking PSA activity in vitro. (c) 2005 Elsevier Ltd. All rights reserved.