Synthesis and anti-viral evaluation of 4'-substituted nucleoside derivatives

• Project/Area Number: 23790141
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Drug development chemistry
• Research Institution: Showa University
• Principal Investigator: KUBOTA Yutaka 昭和大学, 薬学部, 助教 (50365714)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 生物活性物質 / ヌクレオシド誘導体 / 抗ウイルス化合物 / 核酸誘導体 / 抗腫瘍化合物

Research Abstract

With an aim to discovery of novel anti-viral/tumor agents, I have developed a new method for the synthesis of 4’-substituted cordycepin derivatives by substitution of a phenylsulfanyl leaving group. Anti-viral evaluation of 4’-substituted cordycepin found some compounds having an activity against RNA virus.

Research Products

• [Journal Article] Elijah Paintsil, Yung-Chi Cheng, From the Chemistry of Epoxy-Sugar Nucleosides to the Discovery of Anti-HIV Agent 4'-ethynylstavudine-Festinavir (2013)
  • Author(s): Kazuhiro Haraguchi, Shingo Takeda, Yutaka Kubota, Hiroki Kumamoto, Hiromichi Tanaka, Takayuki Hamasaki, Masanori Baba
  • Journal Title: Current Pharmaceutical Design Volume: Vol.19, No.10 Pages: 1880-1897
  • Peer Reviewed
• [Journal Article] Phenylsulfanylation of 3',4'-Unsaturated Adenosine Employing Thiophenol-N-Iodosuccinimide Leads to 4'-Phenylsulfanylcordycepin: Synthesis of 4'-Substituted Cordycepins on the Basis of Substitution of the Phenylsulfanyl Leaving Group (2011)
  • Author(s): Yutaka Kubota, Mariko Ehara, Kazuhiro Haraguchi, Hiromichi Tanaka
  • Journal Title: The Journal of Organic Chemistry Volume: Vol. 76, No. 21 Pages: 8710-8717
  • Peer Reviewed
• [Journal Article] Phenylsulfanylation of 3', 4'-unsaturated adenosine employing thiophenol-N-iodosuccinimide leads to 4'-phenylsulfanylcordycepin : synthesis of 4'-substituted cordycepins on the basis of substitution of the phenylsulfanyl leaving group (2011)
  • Author(s): Kazuhiro Haraguchi
  • Journal Title: J.Org.Chem. Volume: 76 Issue: 21 Pages: 8710-8717
  • DOI: 10.1021/jo201246y
  • Peer Reviewed
• [Presentation] 新規逆転写酵素阻害剤の創製を指向した4'位置換β-L-チミジンの合成研究 (2012)
  • Author(s): 窪田 豊、須賀真理奈、熊本浩樹、原口一広
  • Place of Presentation: 昭和大学(東京)
  • Year and Date: 2012-10-13
• [Presentation] 1'-シアノチミジンのANP誘導体の合成研究 (2012)
  • Author(s): 原口一広、窪田 豊、鶴賀 伶
  • Place of Presentation: 昭和大学(東京)
  • Year and Date: 2012-10-13
• [Presentation] 1'位にメチル基を有するジオキソラニルヌクレオシドの合成とその抗HCV活 性 (2011)
  • Author(s): 窪田 豊、金田有里、原口一広、加藤宣之、田中博道
  • Organizer: 第21回抗ウイルス療法研究会
  • Place of Presentation: 金沢市文化ホール(石川県)
  • Year and Date: 2011-05-29
• [Presentation] 1'位にﾒﾁﾙ基を有するジオキソラニルヌクレオシドの合成とその抗HCV活性 (2011)
  • Author(s): 窪田 豊、金田有理、原口一広、加藤宣之、田中博道
  • Organizer: 第21回抗ウイルス療法研究会
  • Place of Presentation: 金沢市文化ホール（石川県）