Synthetic study of euphorbias : antitumor and anti-HIV agents

• Project/Area Number: 20790016
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Tohoku Pharmaceutical University
• Principal Investigator: WATANABE Kazuhiro Tohoku Pharmaceutical University, 薬学部, 講師 (10382673)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 抗腫瘍活性物質 / 抗HIV活性物質 / ユーフォルビア類 / 全合成

Research Abstract

A new diterpenoid Euphorbia factor L_<11> was isolated from the seeds of Euphorbia lathyris by Yue and co-workers. The model compound of Euphorbia factor L_<11> was synthesized from cyclopentenone in 14 steps. The key cyclization includes a ring-closing metathesis (RCM) of triene with Grubbs's catalyst.

Research Products

• [Journal Article] Total Synthesis of (+)-Stachyflin : a Potential Anti-influenza A Virus Agent (2010)
  • Author(s): Kazuhiro Watanabe, Junji Sakurai, Hideki Abe, Tadashi Katoh
  • Journal Title: Chem.Commun. 46 Pages: 4055-4057
  • Peer Reviewed
• [Journal Article] Enantioselective Total Synthesis of Novel Diterpenoid Pyrones (+)-Sesquicillin and (-?)-Nalanthalide from Fungal Fermentations (2010)
  • Author(s): Takamasa Oguchi, Kazuhiro Watanabe, Hideki Abe, Tadashi Katoh
  • Journal Title: Heterocycles 80 Pages: 229-250
  • NAID: 40016900101
  • Peer Reviewed
• [Journal Article] Total Synthesis of (+)-Stachyflin : a Potential Anti-influenza A Virus Agent (2010)
  • Author(s): Kazuhiro Watanabe, Junji Sakurai, Hideki Abe, Tadashi Katoh
  • Journal Title: Chem.Commun. Volume: 46 Pages: 4055-4057
  • Peer Reviewed
• [Journal Article] Enantioselective Total Synthesis of Novel Diterpenoid Pyrones (+)-Sesquicillin and (-)-Nalanthalide from Fungal Fermentations (2010)
  • Author(s): Takamasa Oguchi, Kazuhiro Watanabe, Hideki Abe, Tadashi Katoh
  • Journal Title: Heterocycles 80 Pages: 229-250
  • NAID: 40016900101
  • Peer Reviewed
• [Journal Article] Total Synthesis of the Bicyclic Depsipept ide HDAC Inhibitors Spiruchostatins A and B, 5''-epi-Spiruchostatin B, FK228 (FR901228) and PreliminaryEvaluation of Their Biological Activity (2009)
  • Author(s): Koichi Narita, Takuya Kikuchi, Kazuhiro Watanabe, Toshiya Takizawa, Takamasa Oguchi, Kyosuke Kudo, Keisuke Matsuhara, Hideki Abe, Takao Yamori, Minoru Yoshida, Tadashi Katoh
  • Journal Title: Chem.Eur.J. 15 Pages: 11174-11186
  • Peer Reviewed
• [Journal Article] Enantioselective Total Synthesis of (-)-Candelalides A, B and C : Potential Kv1.3 Blocking Immunosuppressive Agents (2009)
  • Author(s): Takamasa Oguchi, Kazuhiro Watanabe, Koichi Ohkubo, Hideki Abe, Tadashi Katoh
  • Journal Title: Chem.Eur.J. 15 Pages: 2826-2845
  • Peer Reviewed
• [Journal Article] Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen (2009)
  • Author(s): Masato Hoshino, Kazuhiro Watanabe, Yosuke Ohtake, Takesi Sato, Hisao Matsuzaki, Reiko Fujita
  • Journal Title: Heterocycles 77 Pages: 263-272
  • NAID: 40016405870
  • Peer Reviewed
• [Journal Article] Stereoslelctive Synthesis of a 4a,9-Disubstituted Octahydroacridine from Isatin (2009)
  • Author(s): Hideki Abe, Yoshimi Sato, Kazuhiro Watanabe, Sakae Aoyagi, Chihiro Kibayashi, Tadashi Katoh
  • Journal Title: Heterocycles 77 Pages: 533-538
  • Peer Reviewed
• [Journal Article] Total Synthesis of the Bicyclic Depsipeptide HDAC Inhibitors Spiruchostatins A and B, 5"-epi-Spiruchostatin B, FK228 (FR901228) and Preliminary Evaluation of Their Biological Activity (2009)
  • Author(s): Koichi Narita, Takuya Kikuchi, Kazuhiro Watanabe, Toshiya Takizawa, Takamasa Oguchi, Kyosuke Kudo, Keisuke Matsuhara, Hideki Abe, Takao Yamori, Minoru Yoshida, Tadashi Katoh
  • Journal Title: Chem.Eur.J. 15 Pages: 11174-11186
  • Peer Reviewed
• [Journal Article] Spirocyclization of Six-membered Cyclic N-Acyliminium Ionswith a Conjugated Diene (2009)
  • Author(s): Hideki Abe, Yoshinori Muramatsu, Kazuhiro Watanabe, Sakae Aoyagi, Chihiro Kibayashi, Tadashi Katoh
  • Journal Title: Heterocycles 79 Pages: 1087-1091
  • Peer Reviewed
• [Journal Article] Enantioselective Total Synthesis of (-) -Candelalides A, B and C : Potential Kv1.3 Blocking Immunosuppressive Agents (2009)
  • Author(s): Takamasa Oguchi, Kazuhiro Watanabe, Koichi Ohkubo, Hideki Abe, Tadashi Katoh
  • Journal Title: Chemistry-A European Journal 15 Pages: 2826-2845
  • Peer Reviewed
• [Journal Article] Total Synthesis of Spiruchostatin A, a Potent Histone Deacetylase Inhibitor (2008)
  • Author(s): Toshiya Takizawa, Kazuhiro Watanabe, Koichi Narita, Kyosuke Kudo, Takamasa Oguchi, Hideki Abe, Tadashi Katoh
  • Journal Title: Heterocycles 65 Pages: 275-290
  • NAID: 40016208573
  • Peer Reviewed
• [Journal Article] Total Synthesis of Spiruchostatin A, a Potent Hi stone Deacetylase Inhibitor (2008)
  • Author(s): Toshiya Takizawa, Kazuhiro Watanabe, Koichi Narita, Kyosuke Kudo, Takamasa Oguchi, Hideki Abe, Tadashi Katoh
  • Journal Title: Heterocycles 65 Pages: 275-290
  • Peer Reviewed
• [Journal Article] Stereoslelctive Synthesis of a 4a, 9-Disubstituted Octahydroacridine from Isatin (2008)
  • Author(s): Hideki Abe, Yoshimi Sato, Kazuhiro Watanabe, Sakae Aoyagi, Chihiro Kibayashi, Tadashi Katoh
  • Journal Title: Heterocycles 77 Pages: 533-538
  • Peer Reviewed
• [Presentation] Enantioselective Total Synthesis of (-)-Candelalides A, B and C : Potential Kv 1.3 Blocking Immunosuppressive Agents (2010)
  • Author(s): Kazuhiro Watanabe, Takamasa Oguchi, Hideki Abe, Tadashi Katoh
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Honolulu
  • Year and Date: 2010-12-19
• [Presentation] Enantioselective Total Synthesis of (-)-Candelalides A, B and C : Potential Kv1.3 Blocking Immunosuppressive Agents. (2010)
  • Author(s): Kazuhiro Watanabe, Takamasa Oguchi, Hideki Abe, Tadashi Katoh
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Honolulu
  • Year and Date: 2010-12-19
• [Presentation] 超原子価ヨウ素試薬PIFAを用いたジメトキシベンジル基の選択的脱保護 (2010)
  • Author(s): 渡邉一弘,_成田紘一,_佐藤静香,_加藤正
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋
  • Year and Date: 2010-11-01
• [Presentation] 超原子価ヨウ素試薬PIFAを活用したジメトキシベンジル基の選択的脱傷護の検討 (2010)
  • Author(s): 渡邉一弘,_成田紘一,_佐藤静香, 加藤正
  • Organizer: 第49回日本薬学会東北支部大会
  • Place of Presentation: 福島県郡山
  • Year and Date: 2010-10-24
• [Presentation] 超原子価ヨウ素試薬PIFAを活用したジメトキシベンジル基の選択的脱保護の検討 (2010)
  • Author(s): 渡邉一弘, 成田紘一, 佐藤静香, 加藤正
  • Organizer: 第49回日本薬学会東北支部大会
  • Place of Presentation: 福島県郡山
  • Year and Date: 2010-10-24
• [Presentation] カンデラリドA,B,Cの全合成 (2010)
  • Author(s): 渡邉一弘, 小口剛正, 成田紘一, 佐藤静香, 加藤正
  • Organizer: 第40回複素環化学討論会
  • Place of Presentation: 仙台
  • Year and Date: 2010-10-15
• [Presentation] 超原子価ヨウ素(III)試薬PIFAを用いた3,4-ジメトキシベンジル基の化学選択的な脱保護 (2010)
  • Author(s): 渡邉一弘, 小口剛正, 阿部秀樹, 加藤正
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
  • Year and Date: 2010-03-29
• [Presentation] カリウムイオンチャンネルKv.1.3阻害活性を有するカンデラリドA-Cの全合成 (2009)
  • Author(s): 渡邉一弘, 小口剛正, 阿部秀樹, 加藤正
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
  • Year and Date: 2009-11-17
• [Presentation] 抗インフルエンザAウイルス活性を有する(+)-スタキブリンの全合成 (2009)
  • Author(s): 渡邉一弘, 櫻井淳二, 阿部秀樹, 加藤正
  • Organizer: 第48回日本薬学会東北支部大会
  • Place of Presentation: 仙台
  • Year and Date: 2009-10-18
• [Presentation] ヒストン脱アセチル化酵素阻害物質スピルコスタチンA,BおよびFK228の全合成 (2009)
  • Author(s): 渡邉一弘, 瀧澤俊也, 成田紘一, 阿部秀樹, 加藤正
  • Organizer: 第50回天然有機化合物討論会
  • Place of Presentation: 福岡
  • Year and Date: 2009-09-30
• [Presentation] ヒストン脱アセチル化酵素阻害剤スピルコスタチンA,B,およびFK228の全合成 (2009)
  • Author(s): 渡邉一弘, 瀧澤俊也, 成田紘一, 佐藤静香, 阿部秀樹, 加藤正
  • Organizer: 第4回東北薬科大学ハイテク・リサーチシンポジウム
  • Place of Presentation: 仙台
  • Year and Date: 2009-05-29
• [Presentation] 抗インフルエンザAウイルス活性を有する(+)-スタキフリンの全合成 (2009)
  • Author(s): 渡邉一弘, 櫻井淳二, 阿部秀樹, 加藤正
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-28
• [Presentation] 抗インフルエンザAウイルス活性を有する (+) -スタキブリンの全合成 (2009)
  • Author(s): 渡邉一弘、櫻井淳二、阿部秀樹、加藤正
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-28
• [Presentation] 抗インフルエンザAスタキフ (2008)
  • Author(s): 渡邉一弘, 櫻井淳二, 阿部秀樹, 加藤正
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2008-11-04
• [Presentation] 抗インフルエンザAウイルス活性物質スタキブリンの全合成 (2008)
  • Author(s): 渡邉一弘, 櫻井淳二, 阿部秀樹, 加藤正
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2008-11-04
• [Presentation] 抗インフルエンザウイルスA活性を有する(+)-スタキブリンの全合成 (2008)
  • Author(s): 渡邉一弘, 櫻井淳二, 阿部秀樹, 加藤正
  • Organizer: 第47回日本薬学会東北支部大会
  • Place of Presentation: 岩手
  • Year and Date: 2008-10-26
• [Presentation] ヒストン脱アセチル化酵素阻害物質スピルコスタチンA, BおよびFK228の全合成 (2008)
  • Author(s): 渡邉一弘, 瀧澤俊也, 成田紘一, 阿部秀樹, 加藤正
  • Organizer: 第50回天然有機化合物討論会
  • Place of Presentation: 福岡
  • Year and Date: 2008-09-30
• [Presentation] ヒストン脱アセチル化酵素阻害剤FK228の全合成 (2008)
  • Author(s): 渡邉一弘, 成田紘一, 阿部秀樹, 加藤正
  • Organizer: 第3回東北薬科大学ハイテク・リサーチシンポジウム
  • Place of Presentation: 仙台
  • Year and Date: 2008-06-13