AlCl3 induced C-N bond formation followed by Pd/C-Cu mediated coupling-cyclization strategy: synthesis of pyrrolo[2,3-b]quinoxalines as anticancer agents |
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Authors: | Bagineni PrasadK Shiva Kumar P Vijaya BabuK Anusha D RambabuAjit Kandale GR VanajaArunasree M Kalle Manojit Pal |
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Institution: | a Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500046, India b Department of Animal Sciences, School of Life Sciences, University of Hyderabad, Hyderabad 500046, India |
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Abstract: | AlCl3 facilitated C-N bond forming reaction between 2,3-dichloroquinoxaline and anilines affording a convenient method for the preparation of N-aryl substituted 3-chloroquinoxalin-2-amines. A related N-benzyl derivative, however, was prepared via a conventional method. These N-alkyl/aryl substituted 3-chloroquinoxalin-2-amines on coupling with terminal alkynes in toluene under Pd/C-Cu catalysis afforded a range of 1,2-disubstituted pyrrolo2,3-b]quinoxalines within 3-5 h in good to excellent yields. Some of the compounds synthesized showed promising anti-proliferative properties when tested in vitro against two cancer cell lines. Docking studies indicated that these molecules interact well with human Akt in silico. |
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Keywords: | 2 3-Dichloroquinoxaline Pyrrolo[2 3-b]quinoxaline AlCl3 Palladium |
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