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

2011 Fiscal Year Final Research Report

• Project/Area Number: 22890175
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Kitasato 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
• 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

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.

Research Products

• [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 Pages: 327-332
  • DOI: DOI:10.1159/000334339.
  • Peer Reviewed
• [Journal Article] An inducible cell-cell fusion system with integrated ability to measure the efficiency and specificity of HIV-1 entry inhibitors (2011)
  • Author(s): Herschhorn A, Finzi A, Jones DM, Courter JR, Sugawara A
  • Journal Title: Sodroski JG PLoS One Volume: 6 Pages: e26731
  • DOI: DOI:10.1371/journal.pone.0026731.
  • Peer Reviewed
• [Journal Article] Solution-phase total synthesis of the hydrophilic natural product argifin using 3, 4, 5-tris(octadecyloxy) benzyl tag (2011)
  • Author(s): Hirose T, Kasai T, Akimoto T, Endo A, Sugawara A, Nagasawa K, Shiomi K, Omura S, Sunazuka T
  • Journal Title: Tetrahedron Volume: 67 Pages: 6633-6643
  • DOI: DOI:10.1016/j.tet.2011.05.073.
  • Peer Reviewed
• [Journal Article] Novel 12-membered non-antibiotic macrolides from erythromycin A ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents (2011)
  • Author(s): Sugawara A, Sueki A, Hirose T, Shima H, Akagawa KS, Omura S, Sunazuka T
  • Journal Title: Bioorg & Med. Chem. Lett Volume: 21 Pages: 3373-3376
  • DOI: DOI:10.1016/j.bmcl.2011.04.004.
  • 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
  • Journal Title: Bioorg & Med. Chem Volume: 19 Pages: 91-101
  • DOI: DOI:10.1016/j.bmc.2010.11.049.
  • 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: Bioorg & Med. Chem Volume: 18 Pages: 5835-5844
  • DOI: DOI:10.1016/j.bmc.2010.06.093.
  • Peer Reviewed
• [Presentation] Novel 12-membered Non-antibiotic Macrolides ; EM900 Series As Novel Leads For Anti-inflammatory And/Or Immunomodulatory Agents (2011)
  • 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
  • Year and Date: 20111129-1202
• [Presentation] Novel 12-membered non-antibiotic macrolides ; EM900 series as novel leads for anti-inflammatory and/or immunomodulatory agents (2011)
  • 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
  • Year and Date: 20110911-14
• [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)
  • Year and Date: 20110822-23
• [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
  • Year and Date: 20110328-31
• [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
  • Year and Date: 20101117-19
• [Remarks]
  • URL: http://seibutuyuuki.sakura.ne.jp/