Effective Preparation of Valuable Biologically Active Compounds Employing Catalytic Construction of Polycyclic Ring System

利用多环体系催化构建有效制备有价值的生物活性化合物

基本信息

项目摘要

When various functional groups exist on a polycyclic skeleton, the three-dimensional relationships of the functional groups are restricted and a specific biological activity would be expected due to the rigid conformation. Therefore, the development of an efficient method for the construction of polycyclic ring systems is highly desired, particularly in the field of medicinal chemistry.Cascade reactions are useful methods for the construction of polycyclic skeletons, which are important cores for biological activities. A variety of cascade reactions, carried out under multiple reaction conditions, such as pericyclic, polar, radical, and transition metal-catalyzed reaction conditions, have been investigated.Culmorin, pentalenene, pentalenic acid, deoxypentalenic acid, longiborneol, cedrandiol, 8, 14-cedranoxide, atisirene, atisine, and estrane-type steroids were synthesized via the intramolecular double Michael reaction. Aza double Michael reaction was applied to the syntheses of tylophorine, epilupinine, tacamonine, and paroxetine. Furthermore, sequential Michael and aldol reactions were performed in both intramolecular and intermolecular manners, leading to the formation of polycyclic compounds fused to a four-membered ring. Synthesis of paesslerin A utilizing a multicomponent cascade reaction revealed an error in the proposed structure.Unique cascade reactions, performed under radical and transition metal-catalyzed reaction conditions, were also investigated. With the combination of several cascade reactions, serofendic acids and methyl 7β-hydroxykaurenoate, both of which have neuroprotective activity, were synthesized in a selective manner.
当多环骨架上存在各种官能团时,官能团的三维关系受到限制,由于刚性构象,可能会产生特定的生物活性。因此,开发一种高效的构建多环环体系的方法是非常必要的,特别是在药物化学领域。级联反应是构建多环骨架的有用方法,而多环骨架是生物活性的重要核心。通过分子内双Michael反应合成了库莫林、五茂烯、五烯酸、脱氧戊烯酸、长冰片、雪松二醇、8,14-雪松、环丁烯和雌烷型甾体。将氮杂双迈克尔反应应用于苯丙氨酸、淫羊藿碱、他卡莫宁和帕罗西汀的合成。此外,连续的Michael和Aldol反应在分子内和分子间进行,导致形成融合成四元环的多环化合物。利用多组分级联反应合成了巴斯莱素A,发现了所提出的结构中的错误。还研究了在自由基和过渡金属催化的反应条件下进行的独特的级联反应。通过几个级联反应的结合,选择性地合成了具有神经保护活性的血清烯酸甲酯和7-β-羟基奎宁酸甲酯。

项目成果

期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Palladium-catalyzed carbon dioxide elimination-fixation reaction of 6-methoxycarbonyloxy-2, 4-hexadien-1-ols.
钯催化的 6-甲氧基羰氧基-2, 4-己二烯-1-醇的二氧化碳消除固定反应。
  • DOI:
  • 发表时间:
    2006
  • 期刊:
  • 影响因子:
    0
  • 作者:
    Kazato Inanaga;Kiyosei Takasu;Masataka Ihara;Kiyosei Takasu 他2名;Kiyosei Takasu 他3名;Kiyosei Takasu 他6名;Kiyosei Takasu 他4名;Yamagishi K.;Yamagishi K.;Masahiro Yoshida;Masahiro Yoshida;Masahiro Yoshida
  • 通讯作者:
    Masahiro Yoshida
Synthesis of Medium-Sized Cyclic γ-Haloketones by Radical Mediated Ring-Opening Reaction of Lewis Acid of Lewis Acid Catalyzed(2+2)-Cycloaddition Product
路易斯酸催化(2+2)-环加成产物自由基介导的路易斯酸开环反应合成中型环状γ-卤代酮
  • DOI:
  • 发表时间:
    2005
  • 期刊:
  • 影响因子:
    0
  • 作者:
    N.Matsuura;Y.Feng;S.Mitsuhashi;D.I.Batovska;稲永風人他2名;K.Shoji;高須清誠他2名
  • 通讯作者:
    高須清誠他2名
A practical catalytic method for preparing highly substituted cyclobutanes and cyclobutenes
Synthesis of Medium-sized γ-Haloketones by Radical Mediated Ring-opening Reaction of Lewis Acid Catalyzed (2+2)-Cycloadducts
路易斯酸催化 (2+2)-环氧化物自由基介导的开环反应合成中型 γ-卤代酮
  • DOI:
  • 发表时间:
    2005
  • 期刊:
  • 影响因子:
    0
  • 作者:
    N.Kagawa;M.Ihara;M.Toyota;M.Ihara;M.Ihara;井原 正隆;高須 清誠 他3名;吉田 昌裕 他2名;高須 清誠 他2名
  • 通讯作者:
    高須 清誠 他2名
Convenient Synthesis of Substituted Piperidinones from a,β-Unsaturated Amides. Formal Synthesis of Deplancheine, Tacamonine, and Paroxetine
从 α,β-不饱和酰胺方便地合成取代哌啶酮 正式合成 Deplancheine、Tacamonine 和 Paroxetine。
  • DOI:
  • 发表时间:
    2005
  • 期刊:
  • 影响因子:
    0
  • 作者:
    K.Takasu;N.Nishida;A.Tomimura;M.Ihara
  • 通讯作者:
    M.Ihara
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IHARA Masataka其他文献

IHARA Masataka的其他文献

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{{ truncateString('IHARA Masataka', 18)}}的其他基金

Efficient Syntheses of Pharmacologically Active Compounds Using Multiple Cascade Reactions
利用多重级联反应有效合成药理活性化合物
  • 批准号:
    15390002
  • 财政年份:
    2003
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Development of Catalytic Asymmetric Careade Reaction and Its Application to Total Syntheses of Bioactive Compounds
催化不对称Careade反应的进展及其在生物活性化合物全合成中的应用
  • 批准号:
    13470466
  • 财政年份:
    2001
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
Synthesis of Polycylic Compounds Possessing Biological Activities by Novel Intramolecular Cascade Reactions
通过新型分子内级联反应合成具有生物活性的多环化合物
  • 批准号:
    09672136
  • 财政年份:
    1997
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for Scientific Research (C)
Synthesis of Camptothecin and Analogs Employing Novel Domino Recation
采用新型多米诺骨牌反应合成喜树碱及其类似物
  • 批准号:
    08557120
  • 财政年份:
    1996
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for Scientific Research (A)
Development of General Methods for Preparation of Versatile Chiral Building Blocks and its Utilization for Syntheses of Biologically Active Compounds
通用手性结构单元制备方法的开发及其在生物活性化合物合成中的应用
  • 批准号:
    02670939
  • 财政年份:
    1990
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)
Syntheses of Biologically Active Natural Products by Intramolecular Double Michael Reaction
分子内双迈克尔反应合成生物活性天然产物
  • 批准号:
    62570929
  • 财政年份:
    1987
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for General Scientific Research (C)

相似海外基金

Research on construction of all-carbon quaternary stereogenic center in fused ring system and asymmetric total synthesis of heterologous bioactive polycyclic compound
稠环体系全碳季立体中心的构建及异源生物活性多环化合物的不对称全合成研究
  • 批准号:
    19H02725
  • 财政年份:
    2019
  • 资助金额:
    $ 9.47万
  • 项目类别:
    Grant-in-Aid for Scientific Research (B)
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