tert-butyl N-[(2S)-1-[4-(hydroxymethyl)anilino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate | 875153-70-1

• 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: tert-butyl N-[(2S)-1-[4-(hydroxymethyl)anilino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 875153-70-1
• 化学式: C₂₁H₂₆N₂O₅
• 分子量: 386.448
• InChiKey: ATCLYNQAMUWFPU-SFHVURJKSA-N

物化性质

• 熔点：
  142-144 °C (decomp)
• 沸点：
  668.8±55.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[4-(hydroxymethyl)anilino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 [4-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]phenyl]methyl N,N-bis(2-hydroxyethyl)carbamate
  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 、 Boc-L-酪氨酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以65%的产率得到tert-butyl N-[(2S)-1-[4-(hydroxymethyl)anilino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
  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

文献信息

• Towards enzyme activated antiprostatic agents
  作者：Graham B Jones、Miguel O Mitchell、James S Weinberg、Anthony V D'Amico、Glenn J Bubley

  DOI：10.1016/s0960-894x(00)00386-3

  日期：2000.9

  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.
• Image contrast agents activated by prostate specific antigen (PSA)
  作者：Graham B. Jones、Longfei Xie、Ahmed El-Shafey、Curtis F. Crasto、Glenn J. Bubley、Anthony V. D’Amico

  DOI：10.1016/j.bmcl.2004.04.041

  日期：2004.6

  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.
• 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.