臺灣博碩士論文加值系統

使用甲醯胺和N-甲基甲醯胺與氧氯化磷合成新型的Vilsmeier 試劑。與N-1-(2-吡啶基)-5-胺基吡唑和N-1-(2-喹啉基)-5-胺基吡唑化合物進行反應。經結構分析鑑定，其產物結構分別為吡唑[3,4-d]嘧啶、N-1-氫-吡唑-5-甲醯胺和N-1-氫-吡唑-5-醋酸甲醚三類化合物，此結果與我們先前使用類似的N-1-(苯基)胺基吡唑和Vilsmeier 試劑進行反應結果不同，先前我們得到分別為甲醯amidinyl吡唑和醋酸甲醚產物之結果有所不同。

Various halomethyleniminium salts as novel Vilsmeier reagents were synthesized from the reaction of formamide or N-methylformamide with phosphoryl chloride. Treatment of N-1-substituted-aminopyrazoles including, N-1-(2-pyridinyl)-5-aminopyrazoles and N-1-(2-quinolinyl)-5-aminopyrazoles with these Vilsmeier reagents to obtain the corresponding pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine products. The experimentant results were different with our previous data which the formylated amidylpyazole and formamidine products were obtained under the similar reaction conditions.

Contents...................................................I
Abbreviation List..........................................X
中文摘要...................................................XI
Abstract...................................................XII
Chapter 1 Introduction.....................................1
Section 1.1 Bioactivity of pyrazole derivatives............1
Section 1.1.1 Pyrazole derivatives as novel CK1 inhibitor lead compounds.............................................1
Section 1.1.2 Pyrazole derivatives as anti-inflammatory lead compounds.............................................3
Section 1.1.3 Pyrazole derivatives as anti-cancer lead compounds..................................................5
Section 1.2.1 Vilsmeier-type reactions.....................7
Section 1.2.2 Application of a Vilsmeier-type reaction.....8
Section 1.2.2.1 Formylation................................8
Section 1.2.2.2 Heterocyclization..........................9
Section 1.2.2.3 Amidination...............................10
Chapter 2 Research approach...............................11
Chapter 3 Results and Discussion..........................13
Section 3.1 Chemistry.....................................13
Section 3.1.1 Synthesis of formylated amidino-pyrazole, N-(1H-pyrazol-5-yl)formamidine, and N-(1H-pyrazol-5-yl)formamide derivatives..................................13
Section 3.1.2 Synthesis of N-(1H-pyrazol-5-yl)formamides..15
Section 3.1.3 Synthesis of pyrazolo[3,4-d]pyrimidines.....19
Section 3.1.4 Synthesis of formamides and formamidines....22
Section 3.2 Bioactivity...................................24
Chapter 4 Conclusion......................................27
Chapter 5 Experimental Section............................30
Section 5.1General Procedure..............................30
Section 5.2 Cell lines....................................45
Section 5.3 Growth inhibition assay.......................46
Reference.................................................47
Addendum..................................................57

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