methyl 2-amino-4-(7-chlorotetrazolo[1,5-a]quinolin-4-yl)-5-oxo-1-(pyridin-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 2-amino-4-(7-chlorotetrazolo[1,5-a]quinolin-4-yl)-5-oxo-1-(pyridin-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: Methyl 2-amino-4-(7-chlorotetrazolo[1,5-a]quinolin-4-yl)-5-oxo-1-pyridin-3-yl-4,6,7,8-tetrahydroquinoline-3-carboxylate；methyl 2-amino-4-(7-chlorotetrazolo[1,5-a]quinolin-4-yl)-5-oxo-1-pyridin-3-yl-4,6,7,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₅H₂₀ClN₇O₃
• 分子量: 501.932
• InChiKey: ZYYJHCQYLROBNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,6-二氯喹啉-3-甲醛 在 哌啶 、 sodium azide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 methyl 2-amino-4-(7-chlorotetrazolo[1,5-a]quinolin-4-yl)-5-oxo-1-(pyridin-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors

  摘要：

  A new series of biquinoline-pyridine hybrids were designed and synthesized by a base-catalyzed cyclocondensation through one-pot multicomponent reaction. All compounds were tested for in vitro anticancer activities against two cancer cell lines A549 (adenocarcinomic human alveolar basal epithelial) and Hep G2 (liver cancer). Enzyme inhibitory activities of all compounds were carried out against EGFR and HER-2 kinase. Of the compounds studied, majority of the compounds showed effective anticancer activity against used cancer cell lines. Compound 9i (IC50 = 0.09 mu M) against EGFR and (IC50 = 0.2 mu M) against HER-2 kinase displayed the most potent inhibitory activity as compared to other member of the series. In the molecular modelling study, compound 9i was bound in to the active pocket of EGFR with four hydrogen bonds and two pi-cation interactions having minimum binding energy Delta G(b) = -54.4 kcal/mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.094

文献信息

• Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors
  作者：Chetan B. Sangani、Jigar A. Makawana、Yong-Tao Duan、Yong Yin、Shashikant B. Teraiya、Nilesh J. Thumar、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.07.094

  日期：2014.9

  A new series of biquinoline-pyridine hybrids were designed and synthesized by a base-catalyzed cyclocondensation through one-pot multicomponent reaction. All compounds were tested for in vitro anticancer activities against two cancer cell lines A549 (adenocarcinomic human alveolar basal epithelial) and Hep G2 (liver cancer). Enzyme inhibitory activities of all compounds were carried out against EGFR and HER-2 kinase. Of the compounds studied, majority of the compounds showed effective anticancer activity against used cancer cell lines. Compound 9i (IC50 = 0.09 mu M) against EGFR and (IC50 = 0.2 mu M) against HER-2 kinase displayed the most potent inhibitory activity as compared to other member of the series. In the molecular modelling study, compound 9i was bound in to the active pocket of EGFR with four hydrogen bonds and two pi-cation interactions having minimum binding energy Delta G(b) = -54.4 kcal/mol. (C) 2014 Elsevier Ltd. All rights reserved.