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Alkylamino derivatives of 4-aminomethylpyridine as inhibitors of copper-containing amine oxidases.

Journal of medicinal chemistry (2005-02-04)
Vincenzo Bertini, Franca Buffoni, Giovanni Ignesti, Nevio Picci, Sonia Trombino, Francesca Iemma, Silvana Alfei, Marco Pocci, Francesco Lucchesini, Angela De Munno
ABSTRACT

The first substratelike, reversible inhibitors of different copper amine oxidases (CAOs) with IC50 (M) as low as 2.0 x 10(-8) corresponding to derivatives of 4-aminomethylpyridine with alkoxy (1a-d), alkylthio (2a,b), and alkylamino (3a-e, 4a-j) groups in the positions 3 and 5 have been prepared and studied. The inhibitors 1a-d are active on benzylamine oxidase and semicarbazide-sensitive amine oxidase and are very selective with respect to diamine oxidase, lysyl oxidase, and monoamine oxidases. The inhibitors 2a,b are selective for benzylamine oxidase whereas 2a is also a new type of good substrate of diamine oxidase. The inhibitors 3a-e and 4a-j are substratelike, reversible, nonselective inhibitors of various CAOs including pea seedling amine oxidase and Hansenula polymorpha amine oxidase, whose enzymatic sites are known from X-ray structure determinations. The inhibitors 3b,c and 4b,c are excellent substratelike tools for studies correlating CAOs that afford crystals suitable for X-ray structure determinations with CAOs from mammals.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%