ethyl 2-amino-4-(5-chloro-1-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl)-7,7-dimethyl-5-oxo-1-(pyridin-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1584694-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-amino-4-(5-chloro-1-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl)-7,7-dimethyl-5-oxo-1-(pyridin-3-yl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 2-amino-4-[5-chloro-1-(4-chlorophenyl)-3-methylpyrazol-4-yl]-7,7-dimethyl-5-oxo-1-pyridin-3-yl-6,8-dihydro-4H-quinoline-3-carboxylate
• CAS: 1584694-06-3
• 化学式: C₂₉H₂₉Cl₂N₅O₃
• 分子量: 566.487
• InChiKey: ATIRNCPNUAGBGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-3-甲基-2-吡唑啉-5-酮 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 2-amino-4-(5-chloro-1-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl)-7,7-dimethyl-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 pyrazole–quinoline–pyridine hybrids as a new class of antimicrobial and anticancer agents

  摘要：

  A new series of pyrazole-quinoline-pyridine hybrids were designed based on molecular hybridization technique and synthesized by a base-catalyzed cyclocondensation reaction through one-pot multicomponent reaction. All compounds were tested for in vitro antibacterial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. Of the compounds studied, majority of the compounds showed effective antibacterial as well as anticancer activity against used strains and cancer cell lines respectively. Compound 7k (IC50 = 0.51 +/- 0.05 mu M) against EGFR and 7b displayed the most potent inhibitory activity with IC50 of 3.1 mu M against FabH as compared to other member of the series. In the molecular modeling study, compound 7k was bound in to the active pocket of EGFR with three hydrogen bond and one pi-cation interaction with minimum binding energy Delta G(b) = -54.6913 kcal/mol, as well as compound 7b was bound in to the active site of FabH with hydrogen bond and pi-sigma interactions with minimum binding energy Delta G(b) = -45.9125 kcal/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.018

文献信息

• Design, synthesis and molecular modeling of pyrazole–quinoline–pyridine hybrids as a new class of antimicrobial and anticancer agents
  作者：Chetan B. Sangani、Jigar A. Makawana、Xin Zhang、Shashikant B. Teraiya、Lin Lin、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2014.01.018

  日期：2014.4

  A new series of pyrazole-quinoline-pyridine hybrids were designed based on molecular hybridization technique and synthesized by a base-catalyzed cyclocondensation reaction through one-pot multicomponent reaction. All compounds were tested for in vitro antibacterial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. Of the compounds studied, majority of the compounds showed effective antibacterial as well as anticancer activity against used strains and cancer cell lines respectively. Compound 7k (IC50 = 0.51 +/- 0.05 mu M) against EGFR and 7b displayed the most potent inhibitory activity with IC50 of 3.1 mu M against FabH as compared to other member of the series. In the molecular modeling study, compound 7k was bound in to the active pocket of EGFR with three hydrogen bond and one pi-cation interaction with minimum binding energy Delta G(b) = -54.6913 kcal/mol, as well as compound 7b was bound in to the active site of FabH with hydrogen bond and pi-sigma interactions with minimum binding energy Delta G(b) = -45.9125 kcal/mol. (C) 2014 Elsevier Masson SAS. All rights reserved.