Development of bioactive compounds containing sugar moiety

• Project/Area Number: 24590020
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Teikyo University
• Principal Investigator: TAKAHASHI Hideyo 帝京大学, 薬学部, 教授 (10266348)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000); Fiscal Year 2014: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000); Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: 軸不斉 / 糖化学 / 立体化学 / グリコシル化 / 軸不性 / グリコシル結合 / 光延反応 / 立体選択的反応 / 抗がん活性 / 立体構造

Outline of Final Research Achievements

The　total　synthesis　of　Rebeccamycin　and　its　derivatives　was investigated.
The synthesized　derivatives were analyzed by NMR and X-ray crystallography to elucidate their conformations.
In the course of the project, the new glycosylation utilizing Mitsunobu reaction was developed. The glycosylation was proceeded under neurtal conditions. It was revealed that the stereoselectivity was controlled by the polarity of the organic solvents.

Research Products

• [Journal Article] A complete gear system in N-benzoyl-carbazole derivatives (2014)
  • Author(s): Hidetsugu Tabata, Susumu Kayama, Yuka Takahashi, Norihiko Tani, Shintaro Wakamatsu, Tomohiko Tasaka, Tetuta Oshitari, Hideaki Natsugari, Hideyo Takahashi
  • Journal Title: Organic Letters Volume: 16 Issue: 5 Pages: 1514
  • DOI: 10.1021/ol500417t
  • Peer Reviewed
• [Journal Article] Conformation and atropisomeric properties of indometacin derivatives (2013)
  • Author(s): Shintaro Wakamatsu, Yuka Takahashi, Hidetsugu Tabata, Tetsuta Oshitari, Norihiko Tani, Isao Azumaya, Yukiteru Katsumoto, Takeyuki Tanaka, Shinzo Hosoi, Hideaki Natsugari, Hideyo Takahashi
  • Journal Title: Chemistry A European Journal Volume: 19 Issue: 22 Pages: 7056
  • DOI: 10.1002/chem.201300064
  • Peer Reviewed
• [Journal Article] Polymethoxyflavones as agents that prevent formation of cataract: Nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells (2013)
  • Author(s): Miyata, Yoshiki; Oshitari, Tetsuta; Okuyama, Yuji; Shimada, Arata; Takahashi, Hideyo; Natsugari, Hideaki; Kosano, Hiroshi.
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 23 Issue: 1 Pages: 183
  • DOI: 10.1016/j.bmcl.2012.10.133
  • Peer Reviewed
• [Journal Article] Minami, Masayasu; Takahashi, Hideyo; Sasaki, Tsukasa; Matsumoto, Shun; Sakai, Kazuhiro; Inagaki, Hirofumi; Yamano, Yuko; Miyake, Hirotsugu (2012)
  • Author(s): The effect of sleep restriction and psychological load on the diurnal metabolic changes in tryptamine-related compounds in human urine
  • Journal Title: Environmental Health and Preventive Medicine Volume: 17 Issue: 2 Pages: 87-97
  • DOI: 10.1007/s12199-011-0222-1
  • Peer Reviewed
• [Presentation] アゾール類のN-アシル体の立体構造 (2014)
  • Author(s): 高橋由佳、嘉山 奨、若松真太朗、田畑英嗣、忍足鉄太、夏苅英昭、高橋秀依
  • Organizer: 第４０回反応と合成の進歩シンポジウム
  • Place of Presentation: 東北大学川内萩ホール
  • Year and Date: 2014-11-10 – 2014-11-11
• [Presentation] クロルプロマジンS-オキシドの立体構造 (2012)
  • Author(s): 高橋秀依、谷紀彦、田畑英嗣、野原雪菜、夏苅英昭
  • Organizer: 第３８回反応と合成の進歩シンポジウム
  • Place of Presentation: 東京
• [Presentation] N-ｽﾙﾎﾆﾙ-１,５-ベンゾジアゼピン誘導体の軸性キラリティー
  • Author(s): 米田哲也、中込純、田畑英嗣、忍足鉄太、高橋秀依、夏苅英昭
  • Organizer: 第５６回日本薬学会関東支部大会
  • Place of Presentation: 東京