4-chloro-8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one | 1157855-13-4

• 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: 4-chloro-8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
• 英文别名: 4-Chlororutaecarpine；16-chloro-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15(20),16,18-octaen-14-one
• CAS: 1157855-13-4
• 化学式: C₁₈H₁₂ClN₃O
• 分子量: 321.766
• InChiKey: FAEYAJSSIQXKLX-UHFFFAOYSA-N

物化性质

• 熔点：
  313-314 °C(Solvent: Ethyl acetate)
• 沸点：
  585.1±60.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-chloro-6-(2-phenylhydrazineylidene)-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one 在 PPA 、 ammonium hydroxide 、 水 作用下， 反应 1.0h， 生成 4-chloro-8,13-dihydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-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

文献信息

• Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C–N Cross-Coupling Reaction
  作者：Guixia Wang、Xiangfei Kong、Dong Chen、Shiqing Li、Jinhua Wang、Tiantian Gou、Linfeng Zhang

  DOI：10.1055/a-1468-6231

  日期：2021.6

  visible-light-initiated cross-dehydrogenative-coupling amination is described, featuring metal- and photocatalyst-free, at room temperature, and using air as an oxidant. The reaction provides a facile approach for the synthesis of rutaecarpine and its derivatives. The substrates with electron-withdrawing groups give higher yields than those with electron-donating groups, but the substituent position

  描述了可见光引发的交叉脱氢偶联胺化，其特征在于在室温下不含金属和光催化剂，并使用空气作为氧化剂。该反应提供了一种合成芸香芸香碱及其衍生物的简便方法。具有吸电子基团的底物比具有给电子基团的底物具有更高的产率，但是取代基位置对产率的影响可忽略不计。使用双萘基-二烷基磷酸氢盐和磷酸二苄基酯作为催化剂，均提供令人满意的产率。这种简单的光驱动策略可能适用于喹唑啉酮衍生物的合成。