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Communication | Special issue | Vol 52, No. 3, 2000, pp.1015-1020
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S116
Synthesis of Polyaminoalkyl Substituted Conjugates of Pyrrolo[2,1-c][1,4]benzodiazepine Involving SNAr Reaction of 2-Nitro-5-fluorobenzoate Precursors

Kiyoshi Matsumoto,* Hirokazu Iida, and J. William Lown*

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


A synthetic procedure is described for conjugating polyaminoalkyl groups to the pyrrolo[2,1-c][1,4]benzodiazepine pharmacophore in order to alter its characteristic DNA sequence binding preference. To this end SNAr reactions of 2-nitro-5-fluorobenzoate esters with different polyaminoalkyl side chains were examined and incorporated in the synthetic scheme.