2-amino-2-(3,5-dihydroxyphenyl)acetonitrile | 1208237-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-2-(3,5-dihydroxyphenyl)acetonitrile
• 英文别名: 2-Amino-2-(3,5-dihydroxyphenyl)acetonitrile
• CAS: 1208237-23-3
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: QLWODTOAMZCKQA-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±30.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-2-(3,5-dihydroxyphenyl)acetonitrile 在 α-aminonitrilase NIT191 from Burkholderia xenovorans 作用下， 以 aq. phosphate buffer 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC–MS

  摘要：

  DOI：

  10.1016/j.molcatb.2014.05.019
• 作为产物：
  描述：

  三甲基氰硅烷 、 3,5-二羟基苯甲醛 在 氨 作用下， 以 甲醇 为溶剂， 反应 5.17h， 以42%的产率得到2-amino-2-(3,5-dihydroxyphenyl)acetonitrile
  参考文献：
  名称：

  Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure–activity relationship studies

  摘要：

  We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K-i values below 20 nM. Among them, compound 32d (K-i = 11 nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.061

文献信息

• Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure–activity relationship studies
  作者：Haofan Wang、Youngjoo Byun、Cyril Barinka、Mrudula Pullambhatla、Hyo-eun C. Bhang、James J. Fox、Jacek Lubkowski、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1016/j.bmcl.2009.10.061

  日期：2010.1

  We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K-i values below 20 nM. Among them, compound 32d (K-i = 11 nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. (C) 2009 Elsevier Ltd. All rights reserved.
• Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC–MS
  作者：Franck Bordier、Mark Stam、Ekaterina Darii、Sabine Tricot、Aurélie Fossey、Johanna Rohault、Adrien Debard、Aline Mariage、Virginie Pellouin、Jean-Louis Petit、Alain Perret、David Vallenet、Marcel Salanoubat、Jean Weissenbach、Carine Vergne-Vaxelaire、Véronique de Berardinis、Anne Zaparucha

  DOI：10.1016/j.molcatb.2014.05.019

  日期：2014.9