Syntheses and conformational analyses of external stimuli responsive aromatic amides

• Project/Area Number: 22590106
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Drug development chemistry
• Research Institution: Showa Pharmaceutical University
• Principal Investigator: OKAMOTO Iwao 昭和薬科大学, 薬学部, 准教授 (80307074)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: 医薬分子設計 / 芳香族アミド / 環境応答 / 機能性分子 / 立体構造 / 酸化還元 / 分子スイッチ

Research Abstract

In nature, a functional molecule, such as a drugs, changes its activity according to its shape called as sterical structure. In this study, we designed and synthesized a series of new aromatic amides, especially external stimuli responsive amides. It is e

Research Products

• [Journal Article] Redox-Responsive Conformational Alteration of Aromatic Amides Bearing N-Quinonyl System (2012)
  • Author(s): Iwao Okamoto, Yusuke Takahashi, Mika Sawamura, Mio Matsumura, Hyuma Masu, Kosuke Katagiri, Isao Azumaya, Masanori Nishino, Yukari Kohama, Nobuyoshi Morita, Osamu Tamura, Hiroyuki Kagechika, Aya Tanatani
  • Journal Title: Tetrahedron Volume: 68 Issue: 27-28 Pages: 5346-5355
  • DOI: 10.1016/j.tet.2012.04.114
  • Peer Reviewed
• [Journal Article] Solvent-dependent Conformational and Fluorescence Change of an N-Phenylbenzohydroxamic Acid Derivative Bearing Two Pyrene Moieties. (2012)
  • Author(s): Misae Kanai, Tomoya Hirano, Isao Azumaya, Iwao Okamoto, Hiroyuki Kagechika, Aya Tanatani
  • Journal Title: Tetrahedron Volume: 68 Issue: 13 Pages: 2778-2783
  • DOI: 10.1016/j.tet.2012.02.012
  • Peer Reviewed
• [Journal Article] Acid-Induced Conformational Alteration of cis-Preferential Aromatic Amides Bearing N-Methyl-N-(2-pyridyl) Moiety (2011)
  • Author(s): Iwao Okamoto, Masayuki Terashima, Hyuma Masu, Mayumi Nabeta, Kaori Ono, Nobuyoshi Morita, Kosuke Katagiri, Isao Azumaya, Osamu Tamura
  • Journal Title: Tetrahedron Volume: 67 Issue: 44 Pages: 8536-8543
  • DOI: 10.1016/j.tet.2011.08.085
  • Peer Reviewed
• [Journal Article] Convenient Synthesis of Aminopyridinecarboxylic Acids (2011)
  • Author(s): Iwao Okamoto, Masayuki Terashima, Rempei Yoshioka, Tomonori Muramatsu, Satomi Kojima, Haruka Inoue, Mio Takahashi, Nobuyoshi Morita, and Osamu Tamura
  • Journal Title: Heterocycles Volume: 83 Issue: 10 Pages: 2343-2352
  • DOI: 10.3987/com-11-12290
  • NAID: 40019008606
  • Peer Reviewed
• [Journal Article] Stereoselective Vinylogous Mannich Reaction of 2-Trimethylsilyloxyfuran on to N-Gulosyl Nitrones (2011)
  • Author(s): Osamu Tamura, Kodai Takeda, Naka Mita, Masanori Sakamoto, Iwao Okamoto, Nobuyoshi Morita, Hiroyuki Ishibashi
  • Journal Title: Organic & Biomolecular Chemistry Volume: 9 Issue: 21 Pages: 7411-7419
  • DOI: 10.1039/c1ob06067h
  • Peer Reviewed
• [Journal Article] Synthesis of the Proposed Structure of Phaeosphaeride A (2011)
  • Author(s): Kenichi Kobayashi, Iwao okamoto, Nobuyoshi Morita
  • Journal Title: Osamu Tamura Organic & Biomolecular Chemistry Volume: 9 Issue: 16 Pages: 5825-5832
  • DOI: 10.1039/c1ob05612c
  • Peer Reviewed
• [Journal Article] Synthesis and Biological Evaluation of Tubulysin D Analogues Related to Stereoisomers of Tubuvaline (2011)
  • Author(s): Taku Shibue, Iwao Okamoto, Nobuyoshi Morita, Hiroshi Morita, Yusuke Hirasawa, Takahiro Hosoya, Osamu Tamura
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 21 Issue: 1 Pages: 431-434
  • DOI: 10.1016/j.bmcl.2010.10.118
  • Peer Reviewed
• [Journal Article] Total Synthesis of Tubulysins (2010)
  • Author(s): Taku Shibue, Toshihiro Hirai, Iwao Okamoto, Nobuyoshi Morita, Hyuma Masu, Isao Azumaya, Osamu Tamura
  • Journal Title: Chemistry - A European Journal Volume: 16 Issue: 38 Pages: 11678-11688
  • DOI: 10.1002/chem.201000963
  • NAID: 110009757677
  • Peer Reviewed
• [Journal Article] Synthesis and Evaluation of Opioid Receptor-binding Affinity ofElaeocarpenine and Its Analogs (2010)
  • Author(s): Haruaki Kurasaki, Iwao Okamoto, Nobuyoshi Morita, Osamu Tamura
  • Journal Title: Bioorganic & Medicinal Chemistry Letters Volume: 20 Issue: 5 Pages: 1601-1603
  • DOI: 10.1016/j.bmcl.2010.01.062
  • Peer Reviewed
• [Journal Article] Oxidative Dimerization of 4-Methoxynaphthylamines in the Presence of Semiconductors (2010)
  • Author(s): Tetsuya Takeya, Yosuke Takahashi, Iwao Okamoto, and Osamu Tamura
  • Journal Title: Heterocycles Volume: 80 Issue: 2 Pages: 1479-1488
  • DOI: 10.3987/com-09-s(s)107
  • NAID: 40016991508
  • Peer Reviewed
• [Presentation] 酸化還元応答型N-メチル芳香族アミドの立体構造変換 (2013)
  • Author(s): 岡本 巌、渋谷 恵佑、高橋 優介、森田 延嘉、田村 修
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: 横浜
  • Year and Date: 2013-03-28
• [Presentation] N,N-ジアリール型芳香族アミドの立体構造特性 (2013)
  • Author(s): 岡本 巌、藤野 大人、丑山 恵子、山中 恵理子、鈴木 めぐみ、加藤 美沙、高橋 優介、森田 延嘉、田村 修
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: 横浜
  • Year and Date: 2013-03-28
• [Presentation] 酸化還元応答型N-メチル芳香族アミドの立体構造変換 (2013)
  • Author(s): 岡本 巌、渋谷 恵佑、高橋 優介、森田 延嘉、田村 修
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜（横浜市）
• [Presentation] N,N-ジアリール型芳香族アミドの立体構造特性 (2013)
  • Author(s): 岡本 巌、藤野 大人、丑山 恵子、山中 恵理子、鈴木 めぐみ、加藤 美沙、高橋 優介、森田 延嘉、田村 修
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜（横浜市）
• [Presentation] Conformational analyses and external stimuli induced conformational alteration of N,N-diaryl amides (2012)
  • Author(s): Iwao Okamoto, Keiko Ushiyama, Eriko Yamanaka, Megumi Suzuki, Misa Kato, Yusuke Takahahsi, Hiroto Fujino, Nobuyoshi Morita, Osamu Tamura
  • Organizer: 244th American Chemical Society National Meeting & Exposition
  • Place of Presentation: Philadelphia, PA, USA
  • Year and Date: 2012-08-21
• [Presentation] 2,6-ピリジル基を有するN-メチル-N-ピリジル芳香族アミドの立体構造特性と構造変換 (2012)
  • Author(s): 岡本 巌、藤掛紗織、寺島正幸、森田延嘉、田村 修
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 札幌
  • Year and Date: 2012-03-30
• [Presentation] 3,5-置換ピリジンによって構築される大環状N-アルキルアミドの合成と立体特性 (2012)
  • Author(s): 岡本 巌、小島絵美、吉岡廉平、森田延嘉、田村 修、桝飛雄真、片桐幸輔、東屋 功
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 札幌
  • Year and Date: 2012-03-30
• [Presentation] 2,6-ピリジル基を有するN-メチル-N-ピリジル芳香族アミドの立体構造特性と構造変換 (2012)
  • Author(s): 藤掛紗織
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(北海道札幌市)
  • Year and Date: 2012-03-30
• [Presentation] 3,5-置換ピリジンによって構築される大環状N-アルキルアミドの合成と立体特性 (2012)
  • Author(s): 小島絵美
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(北海道札幌市)
  • Year and Date: 2012-03-30
• [Presentation] Synthesis and Biological Evaluation of Tubulysins and Their Analogues (2011)
  • Author(s): Taku Shibue, Iwao Okamoto, Nobuyoshi Morita, Hiroshi Morita, Yusuke Hirasawa, Takahiro Hosoya, Osamu Tamura
  • Organizer: AIMECS 11
  • Place of Presentation: Tokyo
  • Year and Date: 2011-12-01
• [Presentation] Phaeosphaeride A の合成研究 (2011)
  • Author(s): 小林健一、岡本 巌、森田延嘉、田村修
  • Organizer: 第37回反応と合成の進歩シンポジウム
  • Place of Presentation: 徳島
  • Year and Date: 2011-11-07
• [Presentation] 含ピリジル型大環状N-メチルアミドの合成と立体特性 (2011)
  • Author(s): 岡本 巌、吉岡廉平、寺島正幸、森田延嘉、田村 修、桝飛雄真、片桐幸輔、東屋 功
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: 筑波
  • Year and Date: 2011-09-22
• [Presentation] 環境応答型アミドの立体特性を基盤とした蛍光センサー分子の創製 (2011)
  • Author(s): 金井美紗衣、平野智也、東屋 功、岡本巌、影近弘之、棚谷 綾
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: 筑波
  • Year and Date: 2011-09-21
• [Presentation] 含ピリジル型大環状N-メチルアミドの合成と立体特性 (2011)
  • Author(s): 岡本巌
  • Organizer: 第22回基礎有機化学討論会
  • Place of Presentation: つくば国際会議場(茨城県つくば市)
  • Year and Date: 2011-09-21
• [Presentation] N-メチル-N-ピリジル芳香族アミドの立体構造特性と酸応答型の構造変換 (2011)
  • Author(s): 寺島正幸
  • Organizer: 日本薬学会 第131年会
  • Place of Presentation: 要旨集上にて発表
  • Year and Date: 2011-03-05
• [Presentation] 含ピリジル・ピリミジル型芳香族N-メチルアミドの自然分晶 (2011)
  • Author(s): 佐久間優子
  • Organizer: 日本薬学会 第131年会
  • Place of Presentation: 要旨集上にて発表
  • Year and Date: 2011-03-05
• [Presentation] Synthesis and conformational analysis of macrocyclic cis-amides bearing pyridines (2011)
  • Author(s): Iwao Okamoto, Rempei Yoshioka, Masayuki Terashima, Nobuyoshi Morita, Osamu Tamura, Hyuma Masu, Isao Azumaya
  • Organizer: 6th International Symposium on Macrocyclic & Supramolecular Chemistry
  • Place of Presentation: Brighton, UK
• [Presentation] N-メチル-N-ピリジル芳香族アミドの立体構造特性と酸応答型の構造変換 (2011)
  • Author(s): 岡本 巌,寺島正幸,鍋田真弓,森田延嘉,田村 修
  • Organizer: 日本薬学会第131年会
• [Presentation] 含ピリジル・ピリミジル型芳香族N-メチルアミドの自然分晶 (2011)
  • Author(s): 岡本 巌,佐久間優子,廣瀬良嗣,杉木雄一,森田延嘉,田村 修,桝 飛雄真,片桐幸輔,東屋 功
  • Organizer: 日本薬学会第131年会
• [Presentation] Synthesis and conformational analysis of macrocyclic cis-amides bearing pyridines (2011)
  • Author(s): 岡本巌
  • Organizer: 6th International Symposium on Macrocyclic & Supramolecular Chemistry
  • Place of Presentation: Sussex University Brighton, UK
• [Presentation] Elaeocarpusアルカロイドの全合成とオピオイド受容体結合能の評価 (2010)
  • Author(s): 倉崎晴彰,岡本 巌,森田延嘉,田村修
  • 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: 2010-11-17
• [Presentation] 酸化還元による環境応答を利用したN,N-ジアリール型芳香族アミドの立体構造変換と機能発現 (2010)
  • Author(s): 岡本 巌,高橋優介,澤村美香,森田延嘉,田村 修,桝飛雄真,東屋 功,影近弘之,松村実生,棚谷綾
  • 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] 酸化還元による環境応答を利用したN,N-ジアリール型芳香族アミドの立体構造変換と機能発現 (2010)
  • Author(s): 岡本巌
  • Organizer: 第36回 反応と合成の進歩シンポジウム
  • Place of Presentation: ウインクあいち(愛知県)
  • Year and Date: 2010-11-01
• [Presentation] N,N-ジアリール型芳香族アミドの酸化還元による立体構造変換と光学特性 (2010)
  • Author(s): 岡本 巌,高橋優介,澤村美香,森田延嘉,田村 修,桝飛雄真,東屋 功,影近弘之,松村実生,棚谷 綾
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-09
• [Presentation] N,N-ジアリール型芳香族アミドの酸化還元による立体構造変換と光学特性 (2010)
  • Author(s): 岡本巌
  • Organizer: 第21回 基礎有機化学討論会
  • Place of Presentation: 名古屋大学東山キャンパス(愛知県)
  • Year and Date: 2010-09-09
• [Presentation] Structural Analyses and Spontaneous Chirality of N-Methyl Aromatic Amides Bearing Pyridines (2010)
  • Author(s): Iwao Okamoto, Yuko Sakuma, Yoshitsugu Hirose, Yuichi Sugiki, Nobuyoshi Morita, Osamu Tamura, Hyuma Masu, Kosuke Katagiri, Isao Azumaya
  • Organizer: Symposium on Molecular Chirality 2010
  • Place of Presentation: Sapporo, Japan
  • Year and Date: 2010-07-11
• [Presentation] Structural Analyses and Spontaneous Chirality of N-Methyl Aromatic Amides Bearing Pyridines (2010)
  • Author(s): 岡本巌
  • Organizer: Symposium on Molecular Chirality 2010
  • Place of Presentation: 札幌コンベンションセンター(北海道)
  • Year and Date: 2010-07-11
• [Presentation] Synthesis and Conformational Analysis of Cyclic N-Methyl Aromatic Amides Bearing Pyridines (2010)
  • Author(s): Iwao Okamoto, Rempei Yoshioka, Terashima Masayuki, Satomi Kojima, Nobuyoshi Morita, Osamu Tamura, Kato Takako, Hyuma Masu, Isao Azumaya
  • Organizer: 5th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: Nara, Japan
  • Year and Date: 2010-06-09
• [Presentation] Synthesis and Conformational Analysis of Cyclic N-Methyl Aromatic Amides Bearing Pyridines (2010)
  • Author(s): 岡本巌
  • Organizer: 5th International Symposium on Macrocyclic & Supramolecular Chemistry
  • Place of Presentation: 奈良県新公会堂(奈良県)
  • Year and Date: 2010-06-09