3-(3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)-2-(4-nitrophenyl)quinazolin-4(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)-2-(4-nitrophenyl)quinazolin-4(3H)-one
• 英文别名: 3-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-2-(4-nitrophenyl)quinazolin-4-one
• 化学式: C₂₉H₂₂N₄O₅
• 分子量: 506.517
• InChiKey: OYIOHEAIQRDUQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基咔唑 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 60.0h， 生成 3-(3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)-2-(4-nitrophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Design and synthesis of 3-(3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)-2-phenylquinazolin-4(3H)-one derivatives to induce ACE inhibitory activity

  摘要：

  In an attempt to develop a new class of cardiovascular drugs, a series of novel carbazolyloxy phenylquinazoline derivatives 9a-g have been synthesized and evaluated as angiotensin converting enzyme (ACE) inhibitors. Most of these compounds exhibited activity as significant ACE inhibitors and three compounds (9b, 9c & 9e) showed maximum inhibitory potency in enzyme based assays. To render support to the experimental results, a series of quinazolinone derivatives were docked into active site of ACE and identified the probable binding modes compared to Lisinopril. Also we have identified common pharmacophore hypothesis (AAADDRR) among the best docked conformers of most potent compounds in a series of compounds. The most potent 9b, 9c, 9e compounds shared common active site with the Lisinopril binding site and retained the key active site residue interactions. The obtained results from pharmacological and molecular modeling studies can be utilized for further optimization of identified hits for selective inhibition of ACE. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.009

文献信息

• Design and synthesis of 3-(3-((9H-carbazol-4-yl)oxy)-2-hydroxypropyl)-2-phenylquinazolin-4(3H)-one derivatives to induce ACE inhibitory activity
  作者：Ramineni Venkatesh、Suresh Kasaboina、Hanmant K. Gaikwad、Sridhara Janardhan、Rajashaker Bantu、Lingaiah Nagarapu、G. Narahari Sastry、Sanjay K. Banerjee

  DOI：10.1016/j.ejmech.2015.04.009

  日期：2015.5

  In an attempt to develop a new class of cardiovascular drugs, a series of novel carbazolyloxy phenylquinazoline derivatives 9a-g have been synthesized and evaluated as angiotensin converting enzyme (ACE) inhibitors. Most of these compounds exhibited activity as significant ACE inhibitors and three compounds (9b, 9c & 9e) showed maximum inhibitory potency in enzyme based assays. To render support to the experimental results, a series of quinazolinone derivatives were docked into active site of ACE and identified the probable binding modes compared to Lisinopril. Also we have identified common pharmacophore hypothesis (AAADDRR) among the best docked conformers of most potent compounds in a series of compounds. The most potent 9b, 9c, 9e compounds shared common active site with the Lisinopril binding site and retained the key active site residue interactions. The obtained results from pharmacological and molecular modeling studies can be utilized for further optimization of identified hits for selective inhibition of ACE. (C) 2015 Elsevier Masson SAS. All rights reserved.