ethyl 6-amino-3-(3-morpholinopropyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate | 1400881-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: ethyl 6-amino-3-(3-morpholinopropyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
• 英文别名: Ethyl 6-amino-3-(3-morpholin-4-ylpropyl)-2-oxo-1,3-benzoxazole-5-carboxylate；ethyl 6-amino-3-(3-morpholin-4-ylpropyl)-2-oxo-1,3-benzoxazole-5-carboxylate
• CAS: 1400881-52-8
• 化学式: C₁₇H₂₃N₃O₅
• 分子量: 349.387
• InChiKey: GIBIQGOJYQKTQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-3-(3-morpholinopropyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate 在 氯化亚砜 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 40.0h， 生成 4-(1-(3-morpholinopropyl)-2-oxo-1,2-dihydrooxazolo[4,5-g]quinazolin-8-ylamino)benzenesulfonamide
  参考文献：
  名称：

  Novel oxazolo[4,5-g]quinazolin-2(1H)-ones: Dual inhibitors of EGFR and Src protein tyrosine kinases

  摘要：

  Quinazoline-containing derivatives are an important class of synthetic products and represent an attractive scaffold for EGFR inhibitors. A series of oxazolo[4,5-g]quinazolin-2(1H)-one derivatives were synthesized and the EGFR and Src inhibition activities were evaluated using Gefitinib as lead compound. The three most potent compounds 5y, 51 and 5a each inhibited EGFR at the IC50 value of 61 nM, 67 nM and 78 nM. Among them, 5c also demonstrated excellent inhibition activity against Src with the IC50 value of 3.1 mu M. Several of these derivatives also showed good anti-proliferation effects against KB and A498 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.055
• 作为产物：
  描述：

  5-苯并噁唑羧酸,2,3-二氢-2-羰基-,乙基酯 在 硝酸 、 铁粉 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 11.0h， 生成 ethyl 6-amino-3-(3-morpholinopropyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
  参考文献：
  名称：

  Novel oxazolo[4,5-g]quinazolin-2(1H)-ones: Dual inhibitors of EGFR and Src protein tyrosine kinases

  摘要：

  Quinazoline-containing derivatives are an important class of synthetic products and represent an attractive scaffold for EGFR inhibitors. A series of oxazolo[4,5-g]quinazolin-2(1H)-one derivatives were synthesized and the EGFR and Src inhibition activities were evaluated using Gefitinib as lead compound. The three most potent compounds 5y, 51 and 5a each inhibited EGFR at the IC50 value of 61 nM, 67 nM and 78 nM. Among them, 5c also demonstrated excellent inhibition activity against Src with the IC50 value of 3.1 mu M. Several of these derivatives also showed good anti-proliferation effects against KB and A498 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.055

文献信息

• Novel oxazolo[4,5-g]quinazolin-2(1H)-ones: Dual inhibitors of EGFR and Src protein tyrosine kinases
  作者：Jinsheng Lin、Wei Shen、Jingwei Xue、Juan Sun、Xue Zhang、Can Zhang

  DOI：10.1016/j.ejmech.2012.06.055

  日期：2012.9

  Quinazoline-containing derivatives are an important class of synthetic products and represent an attractive scaffold for EGFR inhibitors. A series of oxazolo[4,5-g]quinazolin-2(1H)-one derivatives were synthesized and the EGFR and Src inhibition activities were evaluated using Gefitinib as lead compound. The three most potent compounds 5y, 51 and 5a each inhibited EGFR at the IC50 value of 61 nM, 67 nM and 78 nM. Among them, 5c also demonstrated excellent inhibition activity against Src with the IC50 value of 3.1 mu M. Several of these derivatives also showed good anti-proliferation effects against KB and A498 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.