6-(4-Brom-anilino)-2,3-dimethyl-5,8-dioxo-5H,8H-chinoxalin | 14334-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-Brom-anilino)-2,3-dimethyl-5,8-dioxo-5H,8H-chinoxalin
• 英文别名: 6-(4-bromophenyl)amino-2,3-dimethyl-5,8-quinoxalinedione；6-(4-bromo-anilino)-2,3-dimethyl-quinoxaline-5,8-dione；6-(4-Bromoanilino)-2,3-dimethylquinoxaline-5,8-dione
• CAS: 14334-08-8
• 化学式: C₁₆H₁₂BrN₃O₂
• 分子量: 358.194
• InChiKey: KRFHTWRCBWYXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴苯胺 、 2,3-dimethylquinoxaline-5,8-dione 以 乙醇 为溶剂， 反应 10.0h， 以37%的产率得到6-(4-Brom-anilino)-2,3-dimethyl-5,8-dioxo-5H,8H-chinoxalin
  参考文献：
  名称：

  3D-QSAR studies of heterocyclic quinones with inhibitory activity on vascular smooth muscle cell proliferation using pharmacophore-based alignment

  摘要：

  The abnormal proliferation and migration of vascular smooth muscle cells (SMCs) play an important role in the pathology of coronary artery atherosclerosis and restenosis following angioplasty. It was reported that some heterocyclic quinone derivatives such as 6-arylamino-quinoxaline-5,8-diones and 6-arylamino-1H- benzo[d]imidazole-4,7-diones have inhibitory activity on rat aortic smooth muscle cell (RAoSMC) proliferation. To understand the structural basis for antiproliferative activity to design more potent agents, we generated pharmacophore models of representative molecules with high activity using Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Database (GALAHAD) and aligned a series of compounds to the selected pharmacophore model, then performed three-dimensional quantitative structure-activity relationship (3D-QSAR) studies using Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA).Good cross-validated correlations were obtained with CoMFA (resulting in q(2) of 0.734 and r(2) of 0.947) and CoMSIA (resulting in q(2) of 0.736 and r(2) of 0.913). The IC50 values of the heterocyclic quinone derivatives on RAoSMC exhibited a strong correlation with steric and hydrophobic fields of the 3D structure of the molecules, resulting in the reliable prediction of inhibitory activity of the series of compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.062

文献信息

• 3D-QSAR studies of heterocyclic quinones with inhibitory activity on vascular smooth muscle cell proliferation using pharmacophore-based alignment
  作者：Chung-Kyu Ryu、Yoonji Lee、Seul-gi Park、Hea-Jung You、Ra-Young Lee、Seung-Yon Lee、Sun Choi

  DOI：10.1016/j.bmc.2008.09.062

  日期：2008.11

  The abnormal proliferation and migration of vascular smooth muscle cells (SMCs) play an important role in the pathology of coronary artery atherosclerosis and restenosis following angioplasty. It was reported that some heterocyclic quinone derivatives such as 6-arylamino-quinoxaline-5,8-diones and 6-arylamino-1H- benzo[d]imidazole-4,7-diones have inhibitory activity on rat aortic smooth muscle cell (RAoSMC) proliferation. To understand the structural basis for antiproliferative activity to design more potent agents, we generated pharmacophore models of representative molecules with high activity using Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Database (GALAHAD) and aligned a series of compounds to the selected pharmacophore model, then performed three-dimensional quantitative structure-activity relationship (3D-QSAR) studies using Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA).Good cross-validated correlations were obtained with CoMFA (resulting in q(2) of 0.734 and r(2) of 0.947) and CoMSIA (resulting in q(2) of 0.736 and r(2) of 0.913). The IC50 values of the heterocyclic quinone derivatives on RAoSMC exhibited a strong correlation with steric and hydrophobic fields of the 3D structure of the molecules, resulting in the reliable prediction of inhibitory activity of the series of compounds. (C) 2008 Elsevier Ltd. All rights reserved.