6-[(4-acetylphenyl)hydrazinylidene]-8,9-dihydro-7H-pyrido[2,1-b]quinazolin-11-one | 80776-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[(4-acetylphenyl)hydrazinylidene]-8,9-dihydro-7H-pyrido[2,1-b]quinazolin-11-one
• CAS: 80776-77-8
• 化学式: C₂₀H₁₈N₄O₂
• 分子量: 346.389
• InChiKey: VUIJRKKZEPTZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.35
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-[(4-acetylphenyl)hydrazinylidene]-8,9-dihydro-7H-pyrido[2,1-b]quinazolin-11-one 在 PPA 、 ammonium hydroxide 、 水 作用下， 反应 1.0h， 生成 12-Acetylrutaecarpine
  参考文献：
  名称：

  Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)

  摘要：

  Rutaecarpine is the major alkaloid component of Wu-Chu-Yu, a well known Chinese herbal drug. It has been reported that rutaecarpine causes the vasodilator, hypotensive effects by stimulation of CGRP synthesis and release via activation of TRPV1. In present study, 23 rutaecarpine analogues were designed and synthesized. Then, the vasodilator effects of theses compounds were screened by rat aortic ring experiment. The result showed that the 14-N atom of rutaecarpine might be the key site for the activity. The 5-carbonyl might make lower contribution to the effect. And simple substitute in indole-ring or quinazo-line-ring would not enhance the vasodilator effect unless in proper position with proper group. One of these compounds, 10-methylrutaecarpine, exhibited similar effect with rutaecarpine. Further functional experiments showed its vasodilator and hypotensive effect were related to the stimulation of CGRP release via activation of TRPV1. The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.015
• 作为产物：
  描述：

  8,9-二氢-6H-吡啶并[2,1-b]喹唑啉-11(7h)-酮 、 4-氨基苯乙酮 在 盐酸 、 sodium nitrite 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 6-[(4-acetylphenyl)hydrazinylidene]-8,9-dihydro-7H-pyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)

  摘要：

  Rutaecarpine is the major alkaloid component of Wu-Chu-Yu, a well known Chinese herbal drug. It has been reported that rutaecarpine causes the vasodilator, hypotensive effects by stimulation of CGRP synthesis and release via activation of TRPV1. In present study, 23 rutaecarpine analogues were designed and synthesized. Then, the vasodilator effects of theses compounds were screened by rat aortic ring experiment. The result showed that the 14-N atom of rutaecarpine might be the key site for the activity. The 5-carbonyl might make lower contribution to the effect. And simple substitute in indole-ring or quinazo-line-ring would not enhance the vasodilator effect unless in proper position with proper group. One of these compounds, 10-methylrutaecarpine, exhibited similar effect with rutaecarpine. Further functional experiments showed its vasodilator and hypotensive effect were related to the stimulation of CGRP release via activation of TRPV1. The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.015