Synthetic Studies on Poison-frog Alkaloids As Antagonists on nicotinic Acetylcholine Receptors
Project/Area Number |
17590004
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | University of Toyama |
Principal Investigator |
TOYOOKA Naoki University of Toyama, 大学院・医学薬学研究部, 准教授 (10217565)
|
Co-Investigator(Kenkyū-buntansha) |
TSUNEKI Hiroshi 富山大学, 大学院・医学薬学研究部, 准教授 (20332661)
SASAOKA Toshiyasu 富山大学, 大学院・医学薬学研究部, 教授 (00272906)
|
Project Period (FY) |
2005 – 2008
|
Project Status |
Completed (Fiscal Year 2008)
|
Budget Amount *help |
¥4,100,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥600,000)
Fiscal Year 2008: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2007: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2005: ¥500,000 (Direct Cost: ¥500,000)
|
Keywords | 毒ガエルアルカロイド / ニコチン受容体 / 179 / 207E / ヒドロキシインドリチジン / monomorine I / 231C / 221I / epi-193E / 233A / 235U / 251AA / インドリチジン / 251N / 221K / NIH / 5,8位置換インドリチジン |
Research Abstract |
毒ガエルアルカロイド類の柔軟で効率的な合成研究を実施し、5, 8位置換インドリチジン、1, 4位置換キノリチジンおよび5, 8位置換6, 7-デヒドロインドリチジンの合成を達成した。これにより、数種のアルカロイドの絶対配置、相対配置を確定した。また、提出構造の誤りを指摘し、訂正構造式の提案を行った。さらに、脳内主要ニコチン受容体に対して、これら毒ガエルアルカロイド類がサブタイプ選択的に抑制作用を示すことも明らかにした。
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Report
(5 results)
Research Products
(38 results)
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[Journal Article] Synthesis, Determination of the Absolute Stereochemistry, and Evaluations at the Nicotinic Acetylcholine Receptors of a Hydroxy-indolizidine Alkaloid from the Ant2009
Author(s)
Zhou, D. ; Toyooka, N.* ; Nemoto, H. ; Yamaguchi, K. ; Tsuneki, H. ; Wada, T. ; Sasaoka, T. ; Sakai, H. ; Tezuka, Y. ; Kadota, S. ; Jones, T.H. ; Garraffo, H.M. ; Spande, T.F. ; Daly, J.W.
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Journal Title
Myrmicaria melanogaster Heterocycles 79
Pages: 565-571
Related Report
Peer Reviewed
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[Journal Article] Synthesis, Determination of the Absolute Stereochemistry, and Evaluations at the Nicotinic Acetylcholine Receptors of a Hydroxyindolizidine Alkaloid from the Ant Myrmicaria melanogaster2009
Author(s)
Zhou, D., Tovooka. N., Nemoto, H., Yamaguchi, K., Tsuneki, H., Wada, T., Sasaoka, T., Sakai, H., Tezuka, Y., Kadota, S., Jones, T. H., Garraffo, H. M., Spande, T. F., Daly, J. W.
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Journal Title
Heterocycles 79
Pages: 565-571
Related Report
Peer Reviewed
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[Journal Article] Synthesis of the Proposed Structure of Poison-Frog Alkaloids 179 and 207Eand Their Inhibitory Effects on Neuronal Nicotinic Acetylcholine Receptors2008
Author(s)
Toyooka, N.* ; Zhou, D. ; Kobayashi, S. ; Tsuneki, H. ; Wada, T. ; Sakai, H. ; Nemoto, H. ; Sasaoka, T. ; Tezuka, Y. ; Subehan ; Kadota, S. ; Garraffo, H.M. ; Spande, T.F. ; Daly, J.W.
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Journal Title
Related Report
Peer Reviewed
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[Journal Article] Synthesis of the Proposed Structure of Poison-Frog Alkaloids 179 and 207E and Their Inhibitory Effects on Neuronal Nicotinic Acetylcholine Receptors2008
Author(s)
Toyooka, N., Zhou, D., Kobaya shi, S., Tsuneki, H., Wada, T., Sakai, H., Nemoto, H., Sasaoka, T., Tezuka, Y., Subehan, Kadota, S., Garraffo, H. M., Spande, T. F., Daly, J. W.
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Journal Title
Related Report
Peer Reviewed
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[Journal Article] First Enantioselective Synthesis of a Hydroxyindolizidine Alkaloid from the Ant Myrmicaria melanogaster2008
Author(s)
Toyooka. N., Zhou, D., Nemot, H., Tezuka, Y., Kadota, S., Jones, T. H., Garraffo, H. M., Spande, T. F., Daly, J. W.
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Journal Title
Related Report
Peer Reviewed
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[Journal Article] Flexible Synthesis of Poison-frog Alkaloids of the 5, 8-Disubstituted Indolizidine-class. II: Synthesis of(-)-209B, (-)-231C, (-)-233D, (-)-235B', (-)-221I, and an Epimer of 193E and Pharmacological Effects at Neuronal Nicotinic Acetylcholine Receptors2007
Author(s)
Kobayashi, S. ; Toyooka, N.* ; Zhou, D. ; Tsuneki, H.* ; Wada, T. ; Sasaoka, T. ; Sakai, H. ; Nemoto, H. ; Garraffo, H.M. ; Spande, T.F. ; Daly, J.W.
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Journal Title
Beilstein J. Org. Chem 3
Pages: 30-30
Related Report
Peer Reviewed
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[Journal Article] Synthesis of Poison-frog Alkaloids 233A, 235U, and 251AA and Their Inhibitory Effects on Neuronal Nicotinic Acetylcholine Receptors2007
Author(s)
Toyooka, N.* ; Kobayashi, S. ; Zhou, D. ; Tsuneki, H. ; Wada, T. ; Sakai, H. ; Nemoto, H. ; Sasaoka, T. ; Garraffo, H.M. ; Spande, T.F. ; Daly, J.W.
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Journal Title
Bioorg. Med. Chem. Lett 17
Pages: 5872-5875
Related Report
Peer Reviewed
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[Journal Article] Synthesis of Poison-frog Alkaloids 233A,235U, and 251AA and Their Inhibitory Effbcts on Neuronal Nicotinic Acetyicholine Receptors2007
Author(s)
Toyooka, N.^*; Kobayashi, S.; Zhou, D.; Tsuneki, H.; Wada, T.; Sakai, H.; Nemoto, H.; Sasaoka, T.; Garraffo, H. M.; Spande, T. F, ; Daly, J. W.
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Journal Title
Bioorg. Med. Chem. Lett 17
Pages: 5872-5875
Related Report
Peer Reviewed
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[Journal Article] Rexlble Synthesis of Poison-frog Aikaloids of the 5,8-Disubstituted Indolizidine-class. II: Synthesis of(-)-209B, (-)-231C, (-)-233D, (-)-235B'',(-)-221I, and an Epimer of 193E and Pharmacological Effects at Neuronal Nicotinlc Acetylcholine Receptors2007
Author(s)
Kobayashl, S.; Toyooka, N.^*; Zhou, D.; Tsuneki, H.; Wada, T.; Sasaoka, T.; Sakai, H.; Nemoto, H.; Garraffo, H. M.; Spande, T. F.; Daly, J. W.
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Journal Title
Beilstein J. Org. Chem 3(online journal)
Pages: 30-30
Related Report
Peer Reviewed
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[Journal Article] The Enantioselective Synthesis of Poison-Frog Alkaloids(-)-203A, (-)-209B,(-)-231C, (-)-233D, and(-)-235B2006
Author(s)
Toyooka, N.* ; Dejun, Z. ; Nemoto, H.* ; Garraffo, H.M. ; Spande, T.F. ; Daly, J.W.
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Journal Title
Tetrahedron Lett 47
Pages: 577-580
Related Report
Peer Reviewed
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[Journal Article] Chiral Synthesis of Poison-frog Alkaloids 251N and 221K2006
Author(s)
Toyooka, N., Zhou, d., Nemoto, H., Garraffo, H.M., Spande, T.F., Daly, J.W.
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Journal Title
Heterocycle 70
Pages: 541-8
NAID
Related Report
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[Journal Article] The enantioselective synthesis of poison-frog alkaloids (-)-203A, (-)-209B, (-)-231C, (-)-233D, and (-)-235B"2006
Author(s)
Toyooka, N., Dejun, Z., Nemoto, H., Garraffo, H.M., Spande, T.F., Daly, J.W.
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Journal Title
Tetrahedron Lett. 47
Pages: 577-580
Related Report
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[Journal Article] Enantioselective syntheses of poison-frog alkaloids : 219F and 221I and an epimer of 193E2006
Author(s)
Toyooka, N., Dejun, Z., Nemoto, H., Garraffo, H.M., Spande, T.F., Daly, J.W.
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Journal Title
Tetrahedron Lett. 47
Pages: 581-582
Related Report
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[Presentation] アリから単離されたヒドロキシインドリチジンアルカロイドの合成2008
Author(s)
豊岡尚樹, 周徳軍, 根本英雄, 山口薫, 恒枝宏史, 和田努, 笹岡利安, 手塚康弘, 門田重利, H. Martin Garraffo, Thomas F. Spande, John W. Daly
Organizer
第38回複素環化学討論会
Place of Presentation
Fukuyama
Related Report
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[Presentation] 毒ガエルアルカロイド179, 207Eの合成2008
Author(s)
豊岡尚樹, 周徳軍, 古林創史, 恒枝宏史, 和田努, 酒井秀紀, 根本英雄, 笹岡利安, 手塚康弘, Subehan, 門田重利, H. Martin Garraffo, Thomas F. Spande, John W. Daly
Organizer
日本薬学会第128年会
Place of Presentation
Yokohama
Related Report
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[Presentation] ピロリチジン型毒ガエルアルカロイドの合成研究2008
Author(s)
周 徳軍, 豊岡尚樹, 根本英雄, 山口 薫, 手塚康弘, 門田重利, Garraffo, H. M., Spande, T. F., Daly, J. W.
Organizer
第34回反応と合成の進歩シンポジウム
Place of Presentation
京都
Related Report
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[Presentation] アリから単離されたヒドロキシインドリチジンアルカロイドの合成2008
Author(s)
豊岡尚樹, 周 徳軍, 根本英雄, 山口 薫, 恒枝宏史, 和田 努, 笹岡利安, 手塚康弘, Garraffo, H. M., Spande, T. F., Daly, J. W., Jones, T. H.
Organizer
第38回複素環化学討論会
Place of Presentation
福山
Related Report
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