[4-(3,5-difluorobenzoylamino)phenyl]carbamic acid tert-butyl ester | 1164350-52-0

• 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: [4-(3,5-difluorobenzoylamino)phenyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[4-[(3,5-difluorobenzoyl)amino]phenyl]carbamate
• CAS: 1164350-52-0
• 化学式: C₁₈H₁₈F₂N₂O₃
• 分子量: 348.349
• InChiKey: AIRLZYRGEKILEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-(3,5-difluorobenzoylamino)phenyl]carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-aminophenyl)-3,5-difluoro-benzamide
  参考文献：
  名称：

  SAR and evaluation of novel 5H-benzo[c][1,8]naphthyridin-6-one analogs as Aurora kinase inhibitors

  摘要：

  Several potent Aurora kinase inhibitors derived from 5H-benzo[c][1,8]naphthyridin-6-one scaffold were identified. A crystal structure of Aurora kinase A in complex with an initial hit revealed a binding mode of the inhibitor within the ATP binding site and provided insight for structure-guided compound optimization. Subsequent SAR campaign provided a potent and selective pan Aurora inhibitor, which demonstrated potent target modulation and antiproliferative effects in the pancreatic cell line, MIAPaCa-2. Furthermore, this compound inhibited phosphorylation of histone H3 (pHH3) in mouse bone morrow upon oral administration, which is consistent with inhibition of Aurora kinase B activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.008
• 作为产物：
  描述：

  特定基氨基甲酸脂酶 、 3,5-二氟苯甲酰氯 在 potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到[4-(3,5-difluorobenzoylamino)phenyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  一种使用酰氯合成酰胺的改进方法

  摘要：

  已经开发了一种简单，温和且高效的条件，用于从酰氯合成酰胺，以最大程度地减少水解，外消旋作用和其他副反应。该方法应扩大肽偶联区域的能力。

  DOI：

  10.1016/j.tetlet.2009.03.220

文献信息

• SAR and evaluation of novel 5H-benzo[c][1,8]naphthyridin-6-one analogs as Aurora kinase inhibitors
  作者：Srinivasa Karra、Yufang Xiao、Xiaoling Chen、Lesley Liu-Bujalski、Bayard Huck、Amanda Sutton、Andreas Goutopoulos、Ben Askew、Kristopher Josephson、Xuliang Jiang、Adam Shutes、Vikram Shankar、Tom Noonan、Gaianne Garcia-Berrios、Rong Dong、Mohanraj Dhanabal、Hui Tian、Zhenxiong Wang、A. Clark、Samantha Goodstal

  DOI：10.1016/j.bmcl.2013.03.008

  日期：2013.5

  Several potent Aurora kinase inhibitors derived from 5H-benzo[c][1,8]naphthyridin-6-one scaffold were identified. A crystal structure of Aurora kinase A in complex with an initial hit revealed a binding mode of the inhibitor within the ATP binding site and provided insight for structure-guided compound optimization. Subsequent SAR campaign provided a potent and selective pan Aurora inhibitor, which demonstrated potent target modulation and antiproliferative effects in the pancreatic cell line, MIAPaCa-2. Furthermore, this compound inhibited phosphorylation of histone H3 (pHH3) in mouse bone morrow upon oral administration, which is consistent with inhibition of Aurora kinase B activity. (C) 2013 Elsevier Ltd. All rights reserved.
• An improved method of amide synthesis using acyl chlorides
  作者：Li Zhang、Xiao-jun Wang、Jing Wang、Nelu Grinberg、DhileepKumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2009.03.220

  日期：2009.6

  A simple, mild and highly efficient condition for amide synthesis from acyl chlorides has been developed to minimize hydrolysis, racemization and other side reactions. This method should expand capabilities in the peptide coupling area.

  已经开发了一种简单，温和且高效的条件，用于从酰氯合成酰胺，以最大程度地减少水解，外消旋作用和其他副反应。该方法应扩大肽偶联区域的能力。