Development of versatile 1, 2-Diamine synthetic methodology and its application for preparation of drug candidates.

• Project/Area Number: 21590013
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kumamoto University
• Principal Investigator: ISHIZUKA Tadao 熊本大学, 大学院・生命科学研究部, 教授 (60176203)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2011: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機化学 / ジアミン / diamine / imidazolone / imidazolidinone / 不斉合成 / 不斉補助剤 / 合成子

Research Abstract

Synthetic strategy for chiral 1, 2-diamines, which are included in many kind of bioactive compounds, has been successfully developed.
The versatile chiral synthon, 4, 5-dimethoxy-2-imidazolidinone, has been prepared by FeCl_3 catalized epoxidation-ring cleavage with H_2O or t-BuOH process followed by optical resolution. Diastereomeric methodology with camphor-derived chiral carboxylic acid has also successed with 93% de.

Research Products

• [Journal Article] A Simple, Iron-catalyzed, Pyridineassisted Hydrogen Peroxide Epoxidation System (2011)
  • Author(s): Mingyu, J., Matsunaga, H., Ishizuka, T.
  • Journal Title: Chemical & Pharmaceutical Bulletin Volume: vol.59 Pages: 799-801
  • Peer Reviewed
• [Journal Article] A Simple, Iron-catalyzed, Pyridine-assisted Hydrogen Peroxide Epoxidation System (2011)
  • Author(s): Mingyu Jiao, Hirofumi Matsunaga, Tadao Ishizuka
  • Journal Title: Chemical & Pharmaceutical Bulletin Volume: 59(in press)
  • NAID: 130000748013
  • Peer Reviewed
• [Journal Article] Sterically congested,"roofed"υ-iminodisulfides as new chiral ligands for palladium-catalyzed, asymmetric allylic alkylation (2010)
  • Author(s): Matsunaga, H., Tokuda, R., Nakajima, M., Ishizuka, T.
  • Journal Title: Chemical & Pharmaceutical Bulletin Volume: vol.58 Pages: 1419-1421
  • Peer Reviewed
• [Journal Article] Sterically congested, "roofed". beta.-iminodisulfides as new chiral ligands for palladium-catalyzed,asymmetric allylic alkylation. (2010)
  • Author(s): Matsunaga, Hirofumi; Tokuda, Ryoh; Nakajima, Makoto; Ishizuka, Tadao.
  • Journal Title: Chemical & Pharmaceutical Bulletin Volume: 58 Pages: 1419-1421
  • NAID: 130000405652
  • Peer Reviewed
• [Presentation] 鉄触媒酸化反応を利用した1, 2-ジアミンキラルシントン合成法の開発 (2012)
  • Author(s): 江下伊織、松永浩文、石塚忠男
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
  • Year and Date: 2012-03-30
• [Presentation] 鉄触媒酸化反応を利用した1,2-ジアミンキラルシントン合成法の開発 (2012)
  • Author(s): 江下伊織
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-30
• [Presentation] 不斉酸化反応を用いた1, 2-ジアミン類キラルシントン効率合成法の開発と応用 (2011)
  • Author(s): 江下伊織、松永浩文、石塚忠男
  • Organizer: 第41回複素環化学討論会
  • Place of Presentation: 崇城大学市民ホール
  • Year and Date: 2011-10-20
• [Presentation] 不斉酸化反応を用いた1,2-ジアミン類キラルシントン効率合成法の開発と応用 (2011)
  • Author(s): 江下伊織
  • Organizer: 第41回複素環化学討論会
  • Place of Presentation: 崇城大学市民ホール(熊本市)
  • Year and Date: 2011-10-20
• [Remarks]
  • URL: http://yakko.pharm.kumamoto-u.ac.jp/