Sterical structure and transformations of outer stimuli responsive N-alkyl pyridylamides

• Project/Area Number: 26460154
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• 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, 教授 (80307074)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 立体構造変換 / 環境応答 / 芳香族アミド / フォールディング / 分子スイッチ

Outline of Final Research Achievements

We have designed a series of pyridyl amides as outer stimuli responsive molecules, especially acidity of surroundings. These amides have N-methyl amide functionality, which has characteristic cis-structure. According to these designs, we have synthesized linear type aromatic oligo amides, macrocyclic oligo amides, and N,N-diaryl type molecular switches.
We found that these novel amides showed sterical transformation according to change of acidity, and some of them showed dynamic transformation, which is different from change of small unit itself.

Research Products

• [Journal Article] Acid-controlled switching of conformational preference of N,N-diarylamides bearing pyridine (2016)
  • Author(s): Ai Ito, Hiroto Fujino, Keiko Ushiyama, Eriko Yamanaka, Ryu Yamasaki, Iwao Okamoto
  • Journal Title: Tetrahedron Letters Volume: 57 Issue: 42 Pages: 4737-4741
  • DOI: 10.1016/j.tetlet.2016.09.035
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Acid- and base-induced conformational alterations of N-aryl-N-troponyl amides (2016)
  • Author(s): Ai Ito, Masanori Sato, Ryu Yamasaki, Iwao Okamoto
  • Journal Title: Tetrahedron Letters Volume: 57 Issue: 3 Pages: 438-441
  • DOI: 10.1016/j.tetlet.2015.12.048
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] N-アリール-N－（２－アズレニル）型芳香族アミドの立体構造特性 (2017)
  • Author(s): 天木崇真、伊藤愛、福田和男、山﨑龍、岡本巌
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパス（宮城県，仙台市）
  • Year and Date: 2017-03-24
• [Presentation] N-(3-チエニル）型芳香族アミドの立体構造特性 (2017)
  • Author(s): 浅見優希、伊藤愛、天木崇真、福田和男、山﨑龍、岡本巌
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 仙台国際センター（宮城県，仙台市）
  • Year and Date: 2017-03-24
• [Presentation] pH-dependent conformational alternation of N,N-diarylamides bearing pyridine and tropolone (2016)
  • Author(s): Ai Ito, Masanori Sato, Hiroto Fujino, Ryu Yamasaki, Iwao Okamoto
  • Organizer: 252nd American Chemical Society National Meeting
  • Place of Presentation: Pennsylvania Convention Center, Philadelphia, PA, USA
  • Year and Date: 2016-08-21
  • Int'l Joint Research
• [Presentation] ピリミジンを有するN-アルキルピリジン-2,6-ジカルボン酸アミドの不斉結晶化 (2016)
  • Author(s): 濱松 朱音、伊藤 愛、佐久間 優子、廣瀬 良嗣、山﨑 龍、桝 飛雄真、東屋 功、岡本 巌
  • Organizer: 日本薬学会第136年会
  • Place of Presentation: パシフィコ横浜（神奈川県，横浜市）
  • Year and Date: 2016-03-26
• [Presentation] 大環状N-アルキルピリジルアミド三量体をホスト分子とした共結晶化 (2015)
  • Author(s): 伊藤 愛、児玉 大樹、張谷 香奈恵、小島 絵美、山﨑 龍、桝 飛雄真、東屋 功、岡本 巌
  • Organizer: 第２６回基礎有機化学討論会
  • Place of Presentation: 愛媛大学城北キャンパス（愛媛県，松山市）
  • Year and Date: 2015-09-24
• [Presentation] N-アルキルニコチン酸アミドとm-ハロピリジンとのカップリング反応による3,5-置換型ピリジン含有アミドの合成と構造解析 (2015)
  • Author(s): 志村 佳恵、張谷 香奈恵、伊藤 愛、山﨑 龍、岡本 巌
  • Organizer: 第５９回日本薬学会関東支部会
  • Place of Presentation: 日本大学薬学部（千葉県，船橋市）
  • Year and Date: 2015-09-12
• [Presentation] pH Dependent molecular folding and unfolding of macrocyclic N-alkyl pyridinecarboxamides (2015)
  • Author(s): Kanae Hariya, Emi Kojima, Rempei Yoshioka, Ai Ito, Ryu Yamasaki, Iwao Okamoto
  • Organizer: 10th International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: Palais de Congres Strasbourg（ストラスブール，フランス）
  • Year and Date: 2015-06-28
  • Int'l Joint Research
• [Presentation] N-アリール-N-トロポニル型芳香族アミドの立体構造特性と酸塩基応答型の構造変換 (2015)
  • Author(s): 佐藤 正規，伊藤 愛，山﨑 龍，岡本 巌
  • Organizer: 日本薬学会第１３５年会
  • Place of Presentation: 神戸学院大学（兵庫県，神戸市）
  • Year and Date: 2015-03-25 – 2015-03-28
• [Presentation] N-ピリジル型およびN-トロポニル型芳香族アミドの立体構造特性と構造変換 (2014)
  • Author(s): 佐藤 正規，伊藤 愛，藤野 大人，山﨑 龍，岡本 巌
  • Organizer: 第４４回 複素環化学討論会
  • Place of Presentation: 札幌市民ホール（北海道，札幌市）
  • Year and Date: 2014-09-10 – 2014-09-12
• [Presentation] Acid-induced folding of aromatic N-methyl amides bearing pyridine-2-carboxamide (2014)
  • Author(s): Saori Fujikake, Ai Ito, Masayuki Terashima, Iwao Okamoto
  • Organizer: 248th ACS National Meeting
  • Place of Presentation: Moscone Center（サンフランシスコ，カリフォルニア州，アメリカ合衆国）
  • Year and Date: 2014-08-10 – 2014-08-14
• [Presentation] Conformational preferences and alteration of N,N-diaryl amides bearing tropolone and pyridine (2014)
  • Author(s): Ai Ito, Masanori Sato, Hiroto Fujino, Iwao Okamoto
  • Organizer: 248th ACS National Meeting
  • Place of Presentation: Moscone Center（サンフランシスコ，カリフォルニア州，アメリカ合衆国）
  • Year and Date: 2014-08-10 – 2014-08-14