N’-(2-cyano-5-(2-chloroethoxy)-4-methoxyphenyl)-N,N-dimethylformamidine | 878375-93-0

• 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: N’-(2-cyano-5-(2-chloroethoxy)-4-methoxyphenyl)-N,N-dimethylformamidine
• 英文别名: N'-(5-(2-chloroethoxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide；N'-[5-(2-chloroethoxy)-2-cyano-4-methoxyphenyl]-N,N-dimethylmethanimidamide
• CAS: 878375-93-0
• 化学式: C₁₃H₁₆ClN₃O₂
• 分子量: 281.742
• InChiKey: CZHDEGOLDMFDTO-UHFFFAOYSA-N

物化性质

• 沸点：
  456.4±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N’-(2-cyano-5-(2-chloroethoxy)-4-methoxyphenyl)-N,N-dimethylformamidine 在 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 4-(3-chloro-4-fluorophenylamino)-6-methoxy-7-(2-((2R,3R,4R,5S)-2-hydroxymethyl-3,4,5-trihydroxy-1-piperidyl)ethoxy)quinazoline
  参考文献：
  名称：

  Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase

  摘要：

  A series of novel quinazoline-1-deoxynojirimycin hybrids were designed, synthesized and evaluated for their inhibitory activities against two drug target enzymes, epidermal growth factor receptor (EGFR) tyrosine kinase and alpha-glucosidase. Some synthesized compounds exhibited significantly inhibitory activities against the tested enzymes. Comparing with reference compounds gefitinib and lapatinib, compounds 7d, 8d, 9b and 9d showed higher inhibitory activities against EGFR (IC50: 1.79-10.71 nM). Meanwhile the inhibitory activities of 7d, 8d and 9c against alpha-glucosidase (IC50 = 0.14, 0.09 and 0.25 mu M, respectively) were obvious higher than that of miglitol (IC50 = 2.43 mu M), a clinical using alpha-glucosidase inhibitor. Interestingly, compound 9d as a dual inhibitor showed high inhibitory activity to EGFR(wt) tyrosine kinase (IC50 = 1.79 nM), also to alpha-glucosidase (IC50 = 0.39 mu M). The work could be very useful starting point for developing a new series of enzyme inhibitors targeting EGFR and/or alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.035
• 作为产物：
  描述：

  在 sodium dithionite 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 2.75h， 生成 N’-(2-cyano-5-(2-chloroethoxy)-4-methoxyphenyl)-N,N-dimethylformamidine
  参考文献：
  名称：

  Quinazoline-1-deoxynojirimycin hybrids as high active dual inhibitors of EGFR and α-glucosidase

  摘要：

  A series of novel quinazoline-1-deoxynojirimycin hybrids were designed, synthesized and evaluated for their inhibitory activities against two drug target enzymes, epidermal growth factor receptor (EGFR) tyrosine kinase and alpha-glucosidase. Some synthesized compounds exhibited significantly inhibitory activities against the tested enzymes. Comparing with reference compounds gefitinib and lapatinib, compounds 7d, 8d, 9b and 9d showed higher inhibitory activities against EGFR (IC50: 1.79-10.71 nM). Meanwhile the inhibitory activities of 7d, 8d and 9c against alpha-glucosidase (IC50 = 0.14, 0.09 and 0.25 mu M, respectively) were obvious higher than that of miglitol (IC50 = 2.43 mu M), a clinical using alpha-glucosidase inhibitor. Interestingly, compound 9d as a dual inhibitor showed high inhibitory activity to EGFR(wt) tyrosine kinase (IC50 = 1.79 nM), also to alpha-glucosidase (IC50 = 0.39 mu M). The work could be very useful starting point for developing a new series of enzyme inhibitors targeting EGFR and/or alpha-glucosidase. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.035

文献信息

• [EN] QUINAZOLINE COMPOUNDS<br/>[FR] COMPOSES DE QUINAZOLINE
  申请人：ASTRAZENECA AB

  公开号：WO2004058752A1

  公开（公告）日：2004-07-15

  Quinazoline derivatives of formula (I) wherein A is 5-membered heteroaryl containing a sulphur atom and optionally containing one or more nitrogen atoms; compositions containing them, processes for their preparation and their use in therapy.

  式(I)中的喹唑啉衍生物，其中A是含有硫原子并且可选地含有一个或多个氮原子的5-成员杂芳基；含有它们的组合物，其制备方法以及它们在治疗中的用途。