Tetrahedron

Colchicine red-ox chemistry revisited: Cathodic behavior and EPR observation of an intermediate radical anion

M Cavazza, L Nucci, E Pannocchia, L Pardi, F Pergola…

Index: Cavazza, Marino; Nucci, Lamberto; Pannocchia, Elisa; Pardi, Lucio; Pergola, Francesco; Pinzino, Calogero; Pietra, Francesco Tetrahedron, 1999 , vol. 55, # 38 p. 11601 - 11608

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Citation Number: 7

Abstract

Colchicine (1), a potently antimitotic alkaloid and useful laboratory tool in cancer research, undergoes cathodic reduction in DMF forming and ESR-observable radical anion (1r) which is characterized by the isotropic hyperfine coupling constants 8.9, 4.3, 0.75, 0.49 and 0.48 G for H-8, H-12, OCH3, H-11 and H-4, respectively, and a much flattened troponoid ring. Assignments are aided by selective deuteriation of colchicine at C-8, C-11 and COCH3, ...