An Innovative synthesis of quinoxalinones and its application to the construction of pharmacophore templates

• Project/Area Number: 24790030
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kyoto University
• Principal Investigator: KOBAYASHI Yusuke 京都大学, 薬学研究科(研究院), 助教 (90509275)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 含窒素複素環 / キノキサリノン / シアノ基 / 空気酸化 / C-N結合形成 / オパビラリン / カロベリン / アタキマスト / Ｃ－Ｎ結合形成

Outline of Final Research Achievements

An efficient method for constructing quinoxalinone-N-oxides from cyanoacetanilides has been developed. This transformation can be achieved
using inexpensive reagents and molecular oxygen under mild conditions, thus offering a practical pathway to quinoxalinone-containing
pharmaceuticals such as ataquimast, caroverine, and opaviraline.

Research Products

• [Journal Article] A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative C-N bond formation (2014)
  • Author(s): Yusuke Kobayashi, Yusuke Suzuki, Tokutaro Ogata, Tetsutaro Kimachi, Yoshiji Takemoto
  • Journal Title: Tetrahedron Letters Volume: 55 Issue: 22 Pages: 3299-3301
  • DOI: 10.1016/j.tetlet.2014.03.061
  • Peer Reviewed
• [Presentation] An Efficient Synthesis of Quinoxalinone-containing Pharmaceuticals via Aerobic Oxidative C-N Bond Formation (2012)
  • Author(s): Yusuke Kobayashi, Tetsutaro Kimachi, Yoshiji Takemoto.
  • Organizer: The 6th Takeda Science Foundation Symposium on Pharmasciences
  • Place of Presentation: 大阪
• [Presentation] An Efficient Synthesis of Quinoxalinone-containing Pharmaceuticals via Aerobic Oxidative C-N Bond Formation (2012)
  • Author(s): Yusuke Kobayashi, Tetsutaro Kimachi, Yoshiji Takemoto.
  • Organizer: IKCOC-12
  • Place of Presentation: 京都
• [Presentation] キノキサリン骨格含有医薬品とその誘導体の効率的合成法の開発 (2012)
  • Author(s): 小林祐輔、來海徹太郎、竹本佳司
  • Organizer: 第30回メディシナルケミストリーシンポジウム
  • Place of Presentation: 東京
• [Presentation] 空気中の酸素を酸化剤亜として利用する酸化的C-Nカップリング反応の開発と応用
  • Author(s): 小林祐輔、來海徹太郎、竹本佳司
  • Organizer: 第32回 有機合成若手セミナー
  • Place of Presentation: 兵庫
• [Remarks]
  • URL: http://www.pharm.kyoto-u.ac.jp/orgchem/04_ron.html
• [Remarks] 学会発表
  • URL: http://www.pharm.kyoto-u.ac.jp/orgchem/05_gak.html