Synthetic investigation of lead compounds possessing antitutor and antiviral activities

具有抗肿瘤和抗病毒活性的先导化合物的合成研究

• 批准号: 13672226
• 负责人: ISHIKURA Minoru
• 金额: $ 0.77万
• 依托单位: Health Sciences University of Hokkaido
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2001
• 资助国家: 日本
• 起止时间: 2001 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-13672226/
• 关键词: indolylborate; cross-coupling reaction; indole alkaloid; ABH; carbocyclic nucleoside; cycloaddition; aziridine; oxirane; ビシクロラクタム; メタセシス; インドール誘導体; ビシクロアミド(ABH); 抗ウィルス活性; インドリボレート; インドール

In this project, the development of synthetic appliobilities of indolylborate and 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) as a valuable synthon of indole alkaloids and carbocyclic nucleoside derivatives was investigated.1. Synthetic study of strychnos and uleine alkaloids through tandem cyclization-cross-coupling reaction with indolylborateConversion of 2-vinylindole derivatives, readily available from the tandem cyclization-cross-coupling reaction of indolylborate wirh (2-bromoprop-2-enyl)pentyl-3-nylamine in a one-pot manner, to strychnos indole alkaloid was investigated.2. Novel approach to the construction of carbazole derivatives through intramolecular alkyl migration reaction.Investigation of intramolecular alkyl migration reaction in indolylborate possessing an electrophilic center was carried out, which provided novel methodology for the construction of carbazole derivatives.3. Synthesis of novel carbocyclic nucleoside derivatives by the use of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH)Cycloaddition reaction toward the double bond of ABH proceeded stereoselectively to provide the exo-adduct. This reaction was used for the construction of novel carbocyclic nucleoside fused with cyclopropane, aziridine and oxirane rings at the 2',3' position of carbocyclic nucleoside derivatives.

在该项目中，研究了吲哚基孔酸盐和2-氮杂环状[2.2.1] HEPT-5-EN-3-ONE（ABH）的合成应用的发展，研究了吲哚生物碱和碳环核苷衍生物的有价值的合成。1。通过串联环化 - 跨核偶联反应与2-乙烯基吲哚衍生物的吲哚基硼酸反应进行串联环化 - 耦合反应的合成研究，可从滴定环化 - 跨核酸反应的tandem环化互相偶联反应中获得（2-溴化苯基）的含量 - 2-溴含量 - 苯基 - 苯基 - 均含量。研究了吲哚生物碱2。通过分子内烷基迁移反应来构建甲Bazole衍生物的新方法。对具有亲电中心的二烷基钻石烷基烷基迁移反应进行了调查，这为癌衍生物的构建提供了新的方法。3。通过使用2-扎布里克洛[2.2.1] Hept-5-en-3-One（ABH）环加度反应对ABH的双键进行立体选择性进行了立体选择，以提供外o型，从而提供了新型碳环核苷衍生物的合成[2.2.1] HEPT-5-EN-3-ONE（ABH）环加成反应。该反应用于构建与环丙烷，氮杂氨酸和氧雷亚环在2'，3'位置的新型碳环核苷的构建。

项目成果

M.Ishikura: "Cycloaddition Reaction of 2-Allenylindoles with Diethyl Acetylenedicarboxylate"J.Heterocyclic Chem.. 38(3). 675-678 (2001)

M.Ishikura：“2-烯基吲哚与乙炔二甲酸二乙酯的环加成反应”J.杂环化​​学.. 38(3)。

Minoru Ishikura: "Synthetic studies of novel carbocyclic nucleosides based on bicyclic amide (ABH)"Trends in Heterocyclic Chemistry. (In press).

Minoru Ishikura：“基于双环酰胺（ABH）的新型碳环核苷的合成研究”杂环化学趋势。

Minoru Ishikura: "Ruthenium-catalyzed ring-opening cross-metathesis reaction of 2-azabicyclo-[2.2.1]hept-5-en-3-one"Heterocycles. 57(2). 241-244 (2002)

Minoru Ishikura：“钌催化的 2-azabicyclo-[2.2.1]hept-5-en-3-one”杂环的开环交叉复分解反应。

M.Ishikura: "A novel c-c bond formation reaction with 1-methoxymethylindolylborate"Chem.Commun.. 3. 220-221 (2002)

M.Ishikura：“与 1-甲氧基甲基吲哚基硼酸酯的新型 c-c 键形成反应”Chem.Commun.. 3. 220-221 (2002)

石倉 稔: "身近な素材に活路を探して"有機合成化学協会誌. 59. 422-423 (2001)

Minoru Ishikura：“在熟悉的材料中寻找出路”合成有机化学学会杂志 59. 422-423 (2001)。