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Toward the total synthesis of a hybrid natural product containing oxabridged cis-decaline-macrolide and it's structure-activity relationships

Research Project

Project/Area Number 22890175
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

SUGAWARA Akihiro  北里大学, 大学院・感染制御科学府, 助教 (50581683)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥2,704,000 (Direct Cost: ¥2,080,000、Indirect Cost: ¥624,000)
Fiscal Year 2011: ¥1,209,000 (Direct Cost: ¥930,000、Indirect Cost: ¥279,000)
Fiscal Year 2010: ¥1,495,000 (Direct Cost: ¥1,150,000、Indirect Cost: ¥345,000)
Keywordsシスデカリン / トリシクロ[5.3.1.^<1, 7> 0^<3, 8>]ウンデカン / ルミナミシン / 抗嫌気性菌活性 / 全合成 / 構造活性相関 / マクロライド / 酸素結束シスデカリン / エノールエーテル / オキサトリシクロウンデカン / 共役14員環エノールエーテル / 抗菌活性のスイッチング
Research Abstract

An efficient synthesis of the key framework of luminamicin, possessing vinyl enol ether, utilizing Stille coupling and Shiina macrolactonization was achieved. Additionally, synthesis of 11-oxatricyclo[5.3.1.^<1, 7> 0^<3, 8>] undecane framework, utilizing cascade Michael-aldol reaction and reaction of oxidative enol etherification was also developed.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (18 results)

All 2011 2010 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (8 results) Remarks (2 results)

  • [Journal Article] Effects of a novel nonantibiotic macrolide, EM900, on cytokine and mucin gene expression in a human airway epithelial cell line.2011

    • Author(s)
      Otsu K, Ishinaga H, Suzuki S, Sugawara A, Sunazuka T, Omura S, Jono H, Takeuchi K.
    • Journal Title

      Pharmacology

      Volume: 88 Issue: 5-6 Pages: 327-32

    • DOI

      10.1159/000334339

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] An inducible cell-cell fusion system with integrated ability to measure the efficiency and specificity of HIV-1 entry inhibitors2011

    • Author(s)
      Herschhorn A, Finzi A, Jones DM, Courter JR, Sugawara A
    • Journal Title

      Sodroski JG PLoS One

      Volume: 6 Issue: 11 Pages: e26731-e26731

    • DOI

      10.1371/journal.pone.0026731

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tag2011

    • Author(s)
      T.Hirose, T.Kasai, T.Akimoto, A.Endo, A.Sugawara, K.Nagasawa, K.Shiomi, S.Omura, T.Sunazuka
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 35 Pages: 6633-6643

    • DOI

      10.1016/j.tet.2011.05.073

    • NAID

      130006995593

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel 12-membered non-antibiotic macrolides from erythromycin A ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents2011

    • Author(s)
      Akihiro Sugawara, Akito Sueki, Tomoyasu Hirose, Kenichiro Nagai, Hiroaki Gouda, Shuichi Hirono, Hideaki Shima, Kiyoko S. Akagawa, Satoshi Omura, Toshiaki Sunazuka
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 21(11) Issue: 11 Pages: 3373-3376

    • DOI

      10.1016/j.bmcl.2011.04.004

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design, synthesis and biological evaluation of small molecule inhibitors of CD4-gp120 binding based on virtual screening2011

    • Author(s)
      Lalonde JM, Elban MA, Courter JR, Sugawara A, Soeta T, Madani N, Princiotto AM, Kwon YD, Kwong PD, Schon A, Freire E, Sodroski J
    • Journal Title

      Bioorg & Med. Chem

      Volume: 19 Issue: 1 Pages: 91-101

    • DOI

      10.1016/j.bmc.2010.11.049

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design, synthesis and biological evaluation of small molecule inhibitors of CD4-gp120 binding based on virtual screening.2011

    • Author(s)
      Lalonde JM, Elban MA, Courter JR, Sugawara A, Soeta T, Madani N, Princiotto AM, Kwon YD, Kwong PD, Schon A, Freire E, Sodroski J, Smith AB 3rd.
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 19 Pages: 91-101

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin2010

    • Author(s)
      Hiroaki Gouda, Toshiaki Sunazuka, Tomoyasu Hirose, Kanami Iguchi, Noriyuki Yamaotsu, Akihiro Sugawara, Yoshihiko Noguchi, Yoshifumi Saito, Tsuyoshi Yamamoto, Takeshi Watanabe, Kazuro Shiomi, Satoshi Omura, Shuichi Hirono
    • Journal Title

      Bioorg. Med. Chem

      Volume: 18(16) Issue: 16 Pages: 5835-5844

    • DOI

      10.1016/j.bmc.2010.06.093

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin.2010

    • Author(s)
      Gouda H, Sunazuka T, Hirose T, Iguchi K, Yamaotsu N, Sugawara A, Noguchi Y, Saito Y, Yamamoto T, Watanabe T, Shiomi K, Omura S, Hirono S.
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 18 Pages: 5835-5844

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Novel 12-membered Non-antibiotic Macrolides ; EM900 Series As Novel Leads For Anti-inflammatory And/Or Immunomodulatory Agents2011

    • Author(s)
      Sugawara A, Sueki A, Hirose T, Nagai K, Gouda K, Hirono S, Shima H, Akagawa KS, Omura S, Sunazuka T
    • Organizer
      8th Asian Federation for Medicinal Chemistry(AFMC) International Medicinal Chemistry Symposium(AIMECS11)
    • Place of Presentation
      Tokyo
    • Related Report
      2011 Final Research Report
  • [Presentation] Novel 12-membered non-antibiotic macrolides ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents2011

    • Author(s)
      Sugawara A, Sueki A, Hirose T, Nagai K, Gouda H, Hirono S, Shima H, Akagawa KS, . mura S, Sunazuka T
    • Organizer
      ICCA12
    • Place of Presentation
      Berlin, Germany
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 抗炎症作用に特化した新規12員環マクロライドEM900の創製と構造活性相関研究2011

    • Author(s)
      菅原章公, 末木啓人, 廣瀬友靖, 赤川清子, 大村智, 砂塚敏明
    • Organizer
      バイオサイエンスフォーラム
    • Place of Presentation
      神奈川県(北里大学)
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 抗炎症作用に特化した新規12員環マクロライドEM900の創製と構造活性相関研究2011

    • Author(s)
      菅原章公, 末木啓人, 廣瀬友靖, 赤川清子, 大村智, 砂塚敏明
    • Organizer
      日本薬学会第131回年会
    • Place of Presentation
      静岡
    • Related Report
      2011 Final Research Report
  • [Presentation] Novel 12-membered non-antibiotic macrolides ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents2011

    • Author(s)
      Sugawara A, Sueki A, Hirose T, Nagai K, Gouda H, Hirono S, Shima H, Akagawa KS, Omura S, Sunazuka T
    • Organizer
      8^<th> Asian Federation for Medicinal Chemistry (AFMC) International Medicinal Chemistry Symposium (AIMECS11)
    • Place of Presentation
      Tokyo, Japan
    • Related Report
      2011 Annual Research Report
  • [Presentation] 抗炎症作用に特化した新規12員環マクロライドの創製と構造活性相関研究2011

    • Author(s)
      菅原章公、末木啓人、廣瀬友靖、赤川清子、大村智、砂塚敏明
    • Organizer
      日本薬学会第131回年会
    • Place of Presentation
      静岡
    • Related Report
      2010 Annual Research Report
  • [Presentation] 抗炎症作用に特化した新規12員環マクロライドEM900の創製と構造活性相関研究2010

    • Author(s)
      菅原章公, 末木啓人, 廣瀬友靖, 赤川清子, 大村智, 砂塚敏明
    • Organizer
      第29回メディシナルケミストリーシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] 抗炎症作用に特化した新規12員環マクロライドの創製と構造活性相関研究2010

    • Author(s)
      菅原章公、末木啓人、廣瀬友靖、赤川清子、大村智、砂塚敏明
    • Organizer
      第29回メディシナルケミストリーシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://seibutuyuuki.sakura.ne.jp/

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://seibutuyuuki.sakura.ne.jp/

    • Related Report
      2011 Annual Research Report

URL: 

Published: 2010-08-27   Modified: 2016-04-21  

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