3-(4-bromobenzyl)-6-nitro-2-propyl-3,4-dihydroquinazolin-4-one | 156483-24-8

• 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: 3-(4-bromobenzyl)-6-nitro-2-propyl-3,4-dihydroquinazolin-4-one
• 英文别名: 3-[(4-Bromophenyl)methyl]-6-nitro-2-propylquinazolin-4-one
• CAS: 156483-24-8
• 化学式: C₁₈H₁₆BrN₃O₃
• 分子量: 402.247
• InChiKey: BOCBSDZJVKQMEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  558.9±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-bromobenzyl)-6-nitro-2-propyl-3,4-dihydroquinazolin-4-one 在 palladium on activated charcoal sodium hydroxide 、 四(三苯基膦)钯 、 甲酸铵 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.5h， 生成 N-{3-[4-(5-Isobutyl-2-sulfamoyl-thiophen-3-yl)-benzyl]-4-oxo-2-propyl-3,4-dihydro-quinazolin-6-yl}-benzamide
  参考文献：
  名称：

  First Reported Nonpeptide AT₁ Receptor Agonist (L-162,313) Acts as an AT₂ Receptor Agonist in Vivo

  摘要：

  In this investigation, it is demonstrated that the first nonpeptide AT, receptor agonist L-162,313 (1), disclosed in 1994, also acts as an agonist at the AT(2) receptor. In anesthetized rats, administration of compound 1 intravenously or locally in the duodenum increased duodenal mucosal alkaline secretion, effects that were sensitive to the selective AT2 receptor antagonist PD-123,319. The data strongly suggest that 1 is an AT2 receptor agonist in vivo. To the best of our knowledge, this substance is the first nonpeptidic low-molecular weight compound with an agonistic effect mediated through the AT2 receptor.

  DOI：

  10.1021/jm031031i
• 作为产物：
  描述：

  对溴溴苄 、 2-Propyl-6-Nitro-Quinazolin-4(1H)-One 在 sodium hydroxide 、 苄基三甲基氢氧化铵 作用下， 以 甲苯 为溶剂， 以46%的产率得到3-(4-bromobenzyl)-6-nitro-2-propyl-3,4-dihydroquinazolin-4-one
  参考文献：
  名称：

  The design, binding affinity prediction and synthesis of macrocyclic angiotensin II AT1 and AT2 receptor antagonists

  摘要：

  Analysis of the SAR of AT(1) selective and AT(1)/AT(2) balanced affinity angiotensin II antagonists led to the design of macrocyclic quinazolinone ligands. CoMFA analysis was used to predict the binding affinities of these novel ligands. The synthesis, X-ray crystal structure, binding affinity and the relevance of these studies to the determination of the biologically relevant binding conformation is discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00116-3

文献信息

• First Reported Nonpeptide AT₁ Receptor Agonist (L-162,313) Acts as an AT₂ Receptor Agonist in Vivo
  作者：Yiqian Wan、Charlotta Wallinder、Berndt Johansson、Mathias Holm、Mahalingam A. K.、Xiongyu Wu、Milad Botros、Anders Karlén、Anders Pettersson、Fred Nyberg、Lars Fändriks、Anders Hallberg、Mathias Alterman

  DOI：10.1021/jm031031i

  日期：2004.3.1

  In this investigation, it is demonstrated that the first nonpeptide AT, receptor agonist L-162,313 (1), disclosed in 1994, also acts as an agonist at the AT(2) receptor. In anesthetized rats, administration of compound 1 intravenously or locally in the duodenum increased duodenal mucosal alkaline secretion, effects that were sensitive to the selective AT2 receptor antagonist PD-123,319. The data strongly suggest that 1 is an AT2 receptor agonist in vivo. To the best of our knowledge, this substance is the first nonpeptidic low-molecular weight compound with an agonistic effect mediated through the AT2 receptor.
• The design, binding affinity prediction and synthesis of macrocyclic angiotensin II AT1 and AT2 receptor antagonists
  作者：Stephen E. de Laszlo、Tomasz W. Glinka、William J. Greenlee、Richard Ball、Robert B. Nachbar、Kristine Prendergast

  DOI：10.1016/0960-894x(96)00116-3

  日期：1996.4

  Analysis of the SAR of AT(1) selective and AT(1)/AT(2) balanced affinity angiotensin II antagonists led to the design of macrocyclic quinazolinone ligands. CoMFA analysis was used to predict the binding affinities of these novel ligands. The synthesis, X-ray crystal structure, binding affinity and the relevance of these studies to the determination of the biologically relevant binding conformation is discussed. Copyright (C) 1996 Elsevier Science Ltd