Cu-mediated N-arylation of 1,2,3-triazin-4-ones: Synthesis of fused triazinone derivatives as potential inhibitors of chorismate mutase

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• 作者：K. Shiva Kumar^a ; Raju Adepu^a ; Sandhya Sandra^a ; D. Rambabu^a ; G. Rama Krishna^b ; C. Malla Reddy^b ; Parimal Misra^a ; Manojit Pal^a ; ^{manojitp@ilsresearch.org} ; ^{manojitpal@rediffmail.com}
• 关键词：1 ; 2 ; 3-Triazin-4-one ; Copper ; Coupling ; Chorismate mutase
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 出版时间：15 January, 2012
• 年：2012
• 卷：22
• 期：2
• 页码：1146-1150
• 全文大小：709 K

文摘

A rapid and direct access to N-aryl substituted fused triazinone derivatives has been accomplished via N-arylation of 1,2,3-triazin-4-one ring involving a Cu-mediated coupling between triazinone derivatives and aryl boronic acids. A combination of Cu(OAc)₂-Et₃N in 1,2-dichloroethane was found to be effective and various fused triazinone derivatives have been prepared by using this methodology. Molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. The scope and limitations of this reaction is discussed. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro. The in vitro dose response study of an active compound is presented.