Rutaecarpane | 38750-15-1

• 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: Rutaecarpane
• 英文别名: 5,7,8,13,13b,14-hexahydroindolo[2’,3’:3,4]pyrido[2,1-b]quinazoline；5,7,8,13,13b,14-hexahydro-indolo[2',3':3,4]pyrido[2,1-b]quinazoline；Rutecarpan；3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaene
• CAS: 38750-15-1
• 化学式: C₁₈H₁₇N₃
• 分子量: 275.353
• InChiKey: WSDMJXYYBOFOEA-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Rutaecarpane 在 叔丁基过氧化氢 、 potassium iodide 、 哌啶 作用下， 以 癸烷 、 乙醇 为溶剂， 反应 37.0h， 以58%的产率得到吴茱萸次碱
  参考文献：
  名称：

  选择性乙酸铜(II)和碘化钾催化缩醛胺氧化为二氢喹唑啉和喹唑啉酮生物碱。

  摘要：

  乙酸铜(II)/乙酸/O2 和碘化钾/叔丁基过氧化氢体系分别影响稠环缩醛胺选择性氧化为二氢喹唑啉和喹唑啉酮。这些方法使得能够容易地制备多种喹唑啉生物碱天然产物及其类似物。

  DOI：

  10.3762/bjoc.9.135
• 作为产物：
  描述：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 、 2-氨基苯甲醛 以 乙醇 为溶剂， 反应 72.0h， 以66%的产率得到Rutaecarpane
  参考文献：
  名称：

  α-Amination of Nitrogen Heterocycles:  Ring-Fused Aminals

  摘要：

  Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine.

  DOI：

  10.1021/ja077473r

文献信息

• 一组四氢吲哚并喹唑啉类化合物及其应用
  申请人：中国医学科学院医药生物技术研究所

  公开号：CN110790762B

  公开（公告）日：2021-06-15

  本发明涉及一组四氢吲哚并喹唑啉类化合物及其应用，所述四氢吲哚并喹唑啉类化合物结构如通式(Ⅰ)所示：其应用为：(1)制备治疗心脑血管疾病的药物；(2)制备提高AMPK、ABCA1、SR‑BI的表达的制剂；(3)制备激活核受体NR活性、抑制NLRP3的活性、IL‑1β的活性、NF‑κB的活性和MAPKs的活性的制剂；(4)制备促进细胞胆固醇外流的制剂；(5)制备抗炎症的药物。
• [EN] GROUP OF TETRAHYDROINDOLOQUINAZOLINE COMPOUNDS AND USE THEREOF<br/>[FR] GROUPE DE COMPOSÉS DE TÉTRAHYDROINDOLOQUINAZOLINE ET LEUR UTILISATION<br/>[ZH] 一组四氢吲哚并喹唑啉类化合物及其应用
  申请人：INST MED BIOTECHNOLOGY CAMS

  公开号：WO2021068773A1

  公开（公告）日：2021-04-15

  本发明涉及一组四氢吲哚并喹唑啉类化合物及其应用，所述四氢吲哚并喹唑啉类化合物结构如通式(Ⅰ)所示。其应用为： (1)制备治疗心脑血管疾病的药物； (2)制备提高AMPK、ABCA1、SR-BI的表达的制剂； (3)制备激活核受体NR活性、抑制NLRP3的活性、IL-1β的活性、NF-κB的活性和MAPKs的活性的制剂； (4)制备促进细胞胆固醇外流的制剂； (5)制备抗炎症的药物。
• 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.
• Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine
  作者：Daniel Seidel、Matthew Richers、Indubhusan Deb、Alena Platonova、Chen Zhang

  DOI：10.1055/s-0033-1338852

  日期：——

  Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine alpha-amination/N-alkylation. This unique alpha-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.
• GROUP OF TETRAHYDROINDOLOQUINAZOLINE COMPOUNDS AND USE THEREOF
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20220402918A1

  公开（公告）日：2022-12-22

  The disclosure relates to an indolo[2′,3′:3,4]pyrido[2,1-b]quinazoline compound represented by general formula (I) and use thereof in the manufacture of (1) a medicament for treating a cardiovascular and cerebrovascular disease, (2) a formulation for increasing expression of AMPK, ABCA1 and SR-BI, (3) a formulation for activating nuclear receptors (NRs), and inhibiting activity of NLRP3, IL-1β, NF-κB and MAPKs, (4) a formulation for promoting cellular cholesterol efflux; or (5) a medicament for anti-inflammation.