Derivatives of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one were prepared in four steps starting from substituted benzonitriles bearing a functionalized amino group in the adjacent position. The unsubstituted- and the dimethoxy-pyrrolizinoindolones 5a and 5b exhibited modest activity against the HL-60(TB) human leukemia cell line, whereas the N-methylated dimethoxy-pyrrolizinoindolone 6b showed to be selective against MOLT-4 leukemia, A549/ATCC, HOP-92, and NCI-H460 non-small cell lung cancer, and CAKI-1 renal cancer cell lines.
Diana, P., Stagno, A., Barraja, P., Montalbano, A., Carbone, A., Parrino, B., et al. (2011). Synthesis of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one. TETRAHEDRON, 67, 3374-3379.
Synthesis of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one
DIANA, Patrizia;BARRAJA, Paola;MONTALBANO, Alessandra;CARBONE, Anna;PARRINO, Barbara;CIRRINCIONE, Girolamo
2011-01-01
Abstract
Derivatives of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one were prepared in four steps starting from substituted benzonitriles bearing a functionalized amino group in the adjacent position. The unsubstituted- and the dimethoxy-pyrrolizinoindolones 5a and 5b exhibited modest activity against the HL-60(TB) human leukemia cell line, whereas the N-methylated dimethoxy-pyrrolizinoindolone 6b showed to be selective against MOLT-4 leukemia, A549/ATCC, HOP-92, and NCI-H460 non-small cell lung cancer, and CAKI-1 renal cancer cell lines.
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