5-butylphenanthridin-6(5H)-one | 37045-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-butylphenanthridin-6(5H)-one
• 英文别名: 5-butylphenanthridin-6-one
• CAS: 37045-21-9
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: ZVLMEBRSAAPUQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2,3-苯并三嗪-4-酮 在 potassium fluoride 、 bis(1,5-cyclooctadiene)nickel (0) 、 18-冠醚-6 、 potassium carbonate 、 双二苯基膦甲烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-butylphenanthridin-6(5H)-one
  参考文献：
  名称：

  镍，1,2,3-苯并三嗪-4（3H）-酮与苯并zy的脱氮环化反应用于构建菲啶酮骨架

  摘要：

  Ni（0）/ dppm催化的具有芳烃的1,2,3-苯并三嗪-4-（3 H）-酮的脱氮环化反应成功地合成了菲啶酮类化合物。制备了各种菲啶酮，收率良好至优异。基于此方法，合成了天然产物N-甲基crinasidine。

  DOI：

  10.1002/adsc.201701143

文献信息

• THERAPEUTIC AGENT FOR HEPATITIS C
  申请人：Baba Masanori

  公开号：US20120316342A1

  公开（公告）日：2012-12-13

  This invention provides a therapeutic agent for hepatitis C comprising, as an active ingredient, a compound having anti-HCV activity useful in treatment of hepatitis C. The therapeutic agent for hepatitis C comprises, as an active ingredient, a compound represented by formula (I) or a pharmaceutically acceptable salt thereof.

  这项发明提供了一种治疗丙型肝炎的药剂，其活性成分为具有抗丙型肝炎病毒活性的化合物，可用于治疗丙型肝炎。治疗丙型肝炎的药剂的活性成分包括由式（I）表示的化合物或其药用可接受的盐。
• Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation
  作者：Xin Geng、Heng He、Andrey Shatskiy、Elena V. Stepanova、Gregory R. Alvey、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.joc.3c01429

  日期：2023.9.1

  Herein, a straightforward synthetic approach for the construction of phenanthridin-6(5H)-one skeletons is disclosed. The developed protocol relies on palladium catalysis, providing controlled access to a range of functionalized phenanthridin-6(5H)-ones in 59–88% yields. Furthermore, plausible reaction pathways are proposed based on mechanistic experiments.

  本文公开了构建菲啶-6(5 H )-酮骨架的简单合成方法。所开发的方案依赖于钯催化，以 59-88% 的产率提供一系列功能化菲啶-6(5 H )-酮的受控访问。此外，基于机械实验提出了合理的反应途径。
• Structure–activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand
  作者：Yuko Nishiyama、Masahiko Nakamura、Takashi Misawa、Madoka Nakagomi、Makoto Makishima、Minoru Ishikawa、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2014.03.007

  日期：2014.5

  Retinoic acid receptor-related orphan receptors (RORs), which belong to the nuclear receptor superfamily, regulate many physiological processes, including hepatic gluconeogenesis, lipid metabolism, immune function and circadian rhythm. Since RORs resemble liver X receptors (LXRs) in the fold structure of their ligand-binding domains, we speculated that ROR-mediated transcription might be modulated by LXR ligands, in line with the multi-template hypothesis. Therefore, we screened our LXR ligand library for compounds with ROR ligand activity and identified a novel ROR ligand with a phenanthridin-6(5H)-one skeleton. Structure-activity relationship studies aimed at separating ROR inverse agonistic activity from LXR-agonistic activity enabled us to develop a series of ROR inverse agonists based on the phenanthridin-6(5H)-one skeleton, including a ROR gamma-selective inverse agonist. (C) 2014 Elsevier Ltd. All rights reserved.
• Structural development studies of anti-hepatitis C virus agents with a phenanthridinone skeleton
  作者：Masahiko Nakamura、Atsushi Aoyama、Mohammed T.A. Salim、Mika Okamoto、Masanori Baba、Hiroyuki Miyachi、Yuichi Hashimoto、Hiroshi Aoyama

  DOI：10.1016/j.bmc.2010.02.057

  日期：2010.4

  A phenanthridinone skeleton was derived from our previous researches on thalidomide and retinoids as a multi-template for generation of anti-viral lead compounds. Structural development studies focusing on anti-hepatitis C virus activity afforded 5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenanthridin-6(5H)-one (10) and 5-butylbenzo[b] phenanthridin-6(5H)-one(39), which showed EC50 values of approximately 3.7 and 3.2 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3<i>H</i> )-ones with Benzynes for Construction of Phenanthridinone Scaffolds
  作者：Vijaykumar H. Thorat、Nitinkumar Satyadev Upadhyay、Masahiro Murakami、Chien-Hong Cheng

  DOI：10.1002/adsc.201701143

  日期：2018.1.17

  The synthesis of phenanthridinones via denitrogenative annulation of 1,2,3‐benzotriazin‐4‐(3H)‐ones with arynes catalysed by Ni(0)/dppm was successfully developed. A variety of phenanthridinones were prepared in good to excellent yields. Based on this method, nature product, N‐methylcrinasidine, was synthesized.

  Ni（0）/ dppm催化的具有芳烃的1,2,3-苯并三嗪-4-（3 H）-酮的脱氮环化反应成功地合成了菲啶酮类化合物。制备了各种菲啶酮，收率良好至优异。基于此方法，合成了天然产物N-甲基crinasidine。