Synthesis and biological activities of some new annulated pyrazolopyranopyrimidines and their derivatives containing indole nucleus

Abstract

The key intermediate 6-amino-3-methyl-4-aryl-1-(5?-substituted- 3?-phenyl-1H-indol-2?-carbonyl)-1,4-dihydropyrano[2,3-c] pyrazol-5-carbonitriles 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n, 3o were prepared by cyclocondensation of 3-methyl-1-(5?-substituted- 3?-phenyl-1H-indol-2?-carbonyl)-5-(4H)-pyrazolones 1a, 1b, 1c with arylidine derivatives of malononitrile 2a, 2b, 2c, 2d, 2e. The compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n, 3o were subjected to cyclocondensation reaction with formamide, formic acid, and carbon disulfide to afford the title compounds 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, and 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j, 6k, 6l, 6m, 6n, 6o, respectively. The structures of all these previously unknown compounds were confirmed by their spectral studies and elemental analysis. These compounds were screened for their antimicrobial and antioxidant activities. © 2013 HeteroCorporation.