2-氰基-N-(2,4,6-三甲基-苯基)-乙酰胺 | 24578-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-N-(2,4,6-三甲基-苯基)-乙酰胺
• 中文别名: 2-氰基-N-(2,4,6-三甲基苯基)-乙酰胺
• 英文名称: 2-Cyano-N-(2,4,6-trimethyl-phenyl)-acetamide
• 英文别名: 2-cyano-N-mesitylacetamide；2-cyano-N-(2,4,6-trimethylphenyl)acetamide
• CAS: 24578-56-1
• 化学式: C₁₂H₁₄N₂O
• mdl: MFCD00278154
• 分子量: 202.256
• InChiKey: WFTLXUGEGQVHGM-UHFFFAOYSA-N

物化性质

• 沸点：
  368.9±30.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-N-(2,4,6-三甲基-苯基)-乙酰胺 、 乙酰氯 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以20%的产率得到N-((2,4,6-trimethyl)phenyl)-2-cyano-3-hydroxybut-2-enamide
  参考文献：
  名称：

  ATP competitive inhibitors of d-alanine–d-alanine ligase based on protein kinase inhibitor scaffolds

  摘要：

  D-Alanine-D-alanine ligase (DDl) is an essential enzyme in bacterial cell wall biosynthesis and an important target for developing new antibiotics. Here, we describe a new approach to identify new inhibitor scaffolds for DDl based on similarity in the ATP binding region of different kinases and DDl. After an initial screening of several protein kinase inhibitors, we found that the Brutons's tyrosine kinase inhibitor LFM-A13, an analog of the Leflunomide metabolite A771726, inhibits DDl with a K-i of 185 mu M. A series of malononitrilamide and salicylamide derivatives of LFM-A13 has been synthesized to confirm the validity of this scaffold as an inhibitor of DDl. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.046
• 作为产物：
  描述：

  氰乙酸 、 2,4,6-三甲基苯胺 在 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-氰基-N-(2,4,6-三甲基-苯基)-乙酰胺
  参考文献：
  名称：

  ATP competitive inhibitors of d-alanine–d-alanine ligase based on protein kinase inhibitor scaffolds

  摘要：

  D-Alanine-D-alanine ligase (DDl) is an essential enzyme in bacterial cell wall biosynthesis and an important target for developing new antibiotics. Here, we describe a new approach to identify new inhibitor scaffolds for DDl based on similarity in the ATP binding region of different kinases and DDl. After an initial screening of several protein kinase inhibitors, we found that the Brutons's tyrosine kinase inhibitor LFM-A13, an analog of the Leflunomide metabolite A771726, inhibits DDl with a K-i of 185 mu M. A series of malononitrilamide and salicylamide derivatives of LFM-A13 has been synthesized to confirm the validity of this scaffold as an inhibitor of DDl. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.046

文献信息

• US4262120A
  申请人：——

  公开号：US4262120A

  公开（公告）日：1981-04-14
• US4400507A
  申请人：——

  公开号：US4400507A

  公开（公告）日：1983-08-23
• ATP competitive inhibitors of d-alanine–d-alanine ligase based on protein kinase inhibitor scaffolds
  作者：Gemma Triola、Stefan Wetzel、Bernhard Ellinger、Marcus A. Koch、Katja Hübel、Daniel Rauh、Herbert Waldmann

  DOI：10.1016/j.bmc.2008.02.046

  日期：2009.2

  D-Alanine-D-alanine ligase (DDl) is an essential enzyme in bacterial cell wall biosynthesis and an important target for developing new antibiotics. Here, we describe a new approach to identify new inhibitor scaffolds for DDl based on similarity in the ATP binding region of different kinases and DDl. After an initial screening of several protein kinase inhibitors, we found that the Brutons's tyrosine kinase inhibitor LFM-A13, an analog of the Leflunomide metabolite A771726, inhibits DDl with a K-i of 185 mu M. A series of malononitrilamide and salicylamide derivatives of LFM-A13 has been synthesized to confirm the validity of this scaffold as an inhibitor of DDl. (C) 2008 Elsevier Ltd. All rights reserved.