2-(2-chloro-6,7-dimethoxyquinazolin-4-ylamino)4,5-dimethoxybenzoic acid | 938515-81-2

• 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: 2-(2-chloro-6,7-dimethoxyquinazolin-4-ylamino)4,5-dimethoxybenzoic acid
• 英文别名: 2-[(2-Chloro-6,7-dimethoxyquinazolin-4-yl)amino]-4,5-dimethoxybenzoic acid
• CAS: 938515-81-2
• 化学式: C₁₉H₁₈ClN₃O₆
• 分子量: 419.821
• InChiKey: RACIFGSPWKFPEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,4-二氯-6,7-二甲氧基喹唑啉 、 2-氨基-4,5-二甲氧基苯甲酸 以 异丙醇 为溶剂， 反应 2.0h， 以52%的产率得到2-(2-chloro-6,7-dimethoxyquinazolin-4-ylamino)4,5-dimethoxybenzoic acid
  参考文献：
  名称：

  Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase

  摘要：

  Two series of new 6-alkoxy-4-substituted-aminoquinazolines (2-4f) and their bioisoteric quinoline congeners (5-7c) were designed and synthesized. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. The newly synthesized compounds were tested in vitro on human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. Most of the tested compounds exploited potent antitumor activity with IC50 values in the nanomolar range in particular compound 3b which displayed the highest activity among the tested compounds with IC50 equal to 0.13 nmol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.038

文献信息

• Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase
  作者：Khaled Abouzid、Samia Shouman

  DOI：10.1016/j.bmc.2008.07.038

  日期：2008.8

  Two series of new 6-alkoxy-4-substituted-aminoquinazolines (2-4f) and their bioisoteric quinoline congeners (5-7c) were designed and synthesized. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. The newly synthesized compounds were tested in vitro on human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. Most of the tested compounds exploited potent antitumor activity with IC50 values in the nanomolar range in particular compound 3b which displayed the highest activity among the tested compounds with IC50 equal to 0.13 nmol. (C) 2008 Elsevier Ltd. All rights reserved.