3-[2-(1H-吲哚-3-基)乙基]-2-(三氟甲基)喹唑啉-4-酮 | 77784-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-[2-(1H-吲哚-3-基)乙基]-2-(三氟甲基)喹唑啉-4-酮
• 英文名称: 3-<2-(3-indolyl)ethyl>-2-(trifluoromethyl)-4(3H)-quinazolinone
• 英文别名: 3-[2-(1H-indol-3-yl)ethyl]-2-(trifluoromethyl)quinazolin-4-one
• CAS: 77784-62-4
• 化学式: C₁₉H₁₄F₃N₃O
• 分子量: 357.335
• InChiKey: ABBNVHRKXQBPTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(1H-吲哚-3-基)乙基]-2-(三氟甲基)喹唑啉-4-酮 在 盐酸 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 吴茱萸次碱
  参考文献：
  名称：

  Studies of rutaecarpine and related quinazolinocarboline alkaloids

  摘要：

  DOI：

  10.1021/jo00208a018
• 作为产物：
  描述：

  色胺 、 2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride 在 palladium(II) trifluoroacetate 、 benzene-1,3,5-triyl triformate 、 sodium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以83%的产率得到3-[2-(1H-吲哚-3-基)乙基]-2-(三氟甲基)喹唑啉-4-酮
  参考文献：
  名称：

  一种2-三氟甲基取代的喹唑啉酮化合物的制备方法以及在合成药物分子中的应用

  摘要：

  本发明公开了一种2‑三氟甲基取代的喹唑啉酮化合物的制备方法，包括如下步骤：将钯催化剂、配体、一氧化碳替代物、添加剂、三氟乙基亚胺酰氯以及胺加入到有机溶剂中，于110℃进行反应16～30小时，反应完全后，后处理得到所述的2‑三氟甲基取代的喹唑啉酮化合物。该制备方法操作简单，起始原料廉价易得，反应效率高，底物兼容性好，还可以通过底物设计合成出不同基团取代的三氟甲基喹唑啉酮化合物，便于操作的同时拓宽了此方法的实用性。该方法也成功地应用于高产率合成药物分子Rutaecarpine(吴茱萸次碱)。

  公开号：

  CN113045503B

文献信息

• Optimization of Rutaecarpine as ABCA1 Up-Regulator for Treating Atherosclerosis
  作者：Yongzhen Li、Tingting Feng、Peng Liu、Chang Liu、Xiao Wang、Dongsheng Li、Ni Li、Minghua Chen、Yanni Xu、Shuyi Si

  DOI：10.1021/ml500131a

  日期：2014.8.14

  ATP-binding cassette transporter A1 (ABCA1) is a key transporter and receptor in promoting cholesterol efflux, and increasing the expression level of ABCA1 is antiatherogenic. In our previous study, rutaecarpine (RUT) was found to protect ApoE(-/-) mice from developing atherosclerosis through preferentially up-regulating ABCA1 expression. In the present work, a series of RUT derivatives were synthesized and examined as ABCA1 expression up-regulators. Compounds CD1, CD6, and BCD1-2 were found to possess the most potential activity as antiatherosclerotic agents among all compounds tested.
• Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)
  作者：Zhuo Chen、Gaoyun Hu、Dai Li、Jun Chen、Yuanjian Li、Huayong Zhou、Ye Xie

  DOI：10.1016/j.bmc.2009.02.015

  日期：2009.3

  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.
• Bergman, Jan; Bergman, Solveig, Heterocycles, 1981, vol. 16, # 3, p. 347 - 350
  作者：Bergman, Jan、Bergman, Solveig

  DOI：——

  日期：——
• Bergman, Jan, Heterocycles, 1984, vol. 21, # 2, p. 404
  作者：Bergman, Jan

  DOI：——

  日期：——
• Studies of rutaecarpine and related quinazolinocarboline alkaloids
  作者：Jan Bergman、Solveig Bergman

  DOI：10.1021/jo00208a018

  日期：1985.4