4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(pent-4-ynyloxy)quinazoline | 1214731-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(pent-4-ynyloxy)quinazoline
• 英文别名: 4-(3''-Chloro-4''-fluoroanilino)-7-methoxy-6-(pent-4-ynyloxy)quinazoline；N-(3-chloro-4-fluorophenyl)-7-methoxy-6-pent-4-ynoxyquinazolin-4-amine
• CAS: 1214731-79-9
• 化学式: C₂₀H₁₇ClFN₃O₂
• 分子量: 385.825
• InChiKey: NUKACQQCRSOUHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(pent-4-ynyloxy)quinazoline 在 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以52%的产率得到4-(3'-chloro-4'-fluorophenylamino)-6-(hexa-4,5-dienyloxy)-7-methoxyquinazoline
  参考文献：
  名称：

  Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines

  摘要：

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.035
• 作为产物：
  描述：

  5-碘-1-戊炔 、 4-(3-氯-4-氟苯胺)-7-甲氧基-喹唑啉-6-醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以59%的产率得到4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(pent-4-ynyloxy)quinazoline
  参考文献：
  名称：

  Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines

  摘要：

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.035

文献信息

• 金(I)类吉非替尼衍生物及其制备方法与应用
  申请人：华中科技大学同济医学院附属同济医院

  公开号：CN117567509A

  公开（公告）日：2024-02-20

  本发明公开了一种金(I)类吉非替尼衍生物及其制备方法与应用，该金(I)类吉非替尼衍生物的制备方法包括如下步骤：1)将化合物I与氢氧化钾溶于甲醇中，加入金配体II，得到混合物；2)将混合物进行搅拌反应，再减压抽滤，得到粗产物；3)将粗产物进行纯化处理，得到产物金(I)类吉非替尼衍生物；本发明的金(I)类吉非替尼衍生物具有EGFR/TrxR双靶点抗肺癌作用，保留吉非替尼的母核结构4‑苯胺基喹唑啉以保证其原有的EGFR靶向抑制活性，引入不同碳链长度的炔基，连接不同的金配体，使其能同时靶向EGFR与TrxR，发挥抗肺癌活性，克服肺癌对吉非替尼的耐药性。
• Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines
  作者：Hyun Seung Ban、Yuko Tanaka、Wataru Nabeyama、Masako Hatori、Hiroyuki Nakamura

  DOI：10.1016/j.bmc.2009.11.035

  日期：2010.1

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.