tert-butyl 2-(1-ethyl-1H-imidazol-4-yl)ethylcarbamate | 1023299-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 2-(1-ethyl-1H-imidazol-4-yl)ethylcarbamate
• 英文别名: tert-butyl N-[2-(1-ethylimidazol-4-yl)ethyl]carbamate
• CAS: 1023299-75-3
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: WJXQFJUFGSCPOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(1-ethyl-1H-imidazol-4-yl)ethylcarbamate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 以44%的产率得到tert-butyl (2-(5-bromo-1-ethyl-1H-imidazol-4-yl)ethyl)carbamate
  参考文献：
  名称：

  2-(1H-Imidazol-4-yl)ethanamine and 2-(1H-pyrazol-1-yl)ethanamine side chain variants of the IGF-1R inhibitor BMS-536924

  摘要：

  A series of IGF-1R inhibitors is disclosed, wherein the (m-chlorophenyl) ethanol side chain of BMS-536924 (1) is replaced with a series of 2-(1H-imidazol-4-yl)ethanamine and 2-(1H-pyrazol-1-yl)ethanamine side chains. Some analogs show improved IGF-1R potency and oral exposure. Analogs from both series, 16a and 17f, show in vivo activity comparable to 1 in our constitutively activated IGF-1R Sal tumor model. This may be the due to the improved protein binding in human and mouse serum for imidazole 16a and the excellent oral exposure of pyrazole 17f. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.049
• 作为产物：
  描述：

  histamine dichloride 在 sodium hydride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 tert-butyl 2-(1-ethyl-1H-imidazol-4-yl)ethylcarbamate
  参考文献：
  名称：

  Facile Syntheses of Histamine- and Imidazole-4-propionic Acid–Derived Room-Temperature Ionic Liquids

  摘要：

  We report synthesis of histamine- and imidazole-4-propionic acid-based ionic liquids containing a variety of alkyl and aryl groups placed at the two different positions of the constituent imidazole ring in convenient steps in good yields.

  DOI：

  10.1080/00397911.2011.555053

文献信息

• Facile Syntheses of Histamine- and Imidazole-4-propionic Acid–Derived Room-Temperature Ionic Liquids
  作者：Ravi Kant Dubey、Neeraj Kumar、Rahul Jain

  DOI：10.1080/00397911.2011.555053

  日期：2012.8.1

  We report synthesis of histamine- and imidazole-4-propionic acid-based ionic liquids containing a variety of alkyl and aryl groups placed at the two different positions of the constituent imidazole ring in convenient steps in good yields.
• 2-(1H-Imidazol-4-yl)ethanamine and 2-(1H-pyrazol-1-yl)ethanamine side chain variants of the IGF-1R inhibitor BMS-536924
  作者：Mark G. Saulnier、David B. Frennesson、Mark D. Wittman、Kurt Zimmermann、Upender Velaparthi、David R. Langley、Charles Struzynski、Xiaopeng Sang、Joan Carboni、Aixin Li、Ann Greer、Zheng Yang、Praveen Balimane、Marco Gottardis、Ricardo Attar、Dolatrai Vyas

  DOI：10.1016/j.bmcl.2008.01.049

  日期：2008.3

  A series of IGF-1R inhibitors is disclosed, wherein the (m-chlorophenyl) ethanol side chain of BMS-536924 (1) is replaced with a series of 2-(1H-imidazol-4-yl)ethanamine and 2-(1H-pyrazol-1-yl)ethanamine side chains. Some analogs show improved IGF-1R potency and oral exposure. Analogs from both series, 16a and 17f, show in vivo activity comparable to 1 in our constitutively activated IGF-1R Sal tumor model. This may be the due to the improved protein binding in human and mouse serum for imidazole 16a and the excellent oral exposure of pyrazole 17f. (C) 2008 Elsevier Ltd. All rights reserved.