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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Aminopyridazines as acetylcholinesterase inhibitors.

Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 microM on homogenized rat striatum AChE), a series of 3-amino-6-phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high AChE inhibition are as follows: (i) presence of a central pyridazine ring, (ii) necessity of a lipophilic cationic head, (iii) change from a 2- to a 4-5-carbon units distance between the pyridazine ring and the cationic head. Among all the derivatives investigated, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6-phenylpyridazine (3y), which shows an IC50 of 0.12 microM on purified AChE (electric eel), was found to be one of the most potent anti- AChE inhibitors, representing a 5000-fold increase in potency compared to minaprine.1[1]


  1. Aminopyridazines as acetylcholinesterase inhibitors. Contreras, J.M., Rival, Y.M., Chayer, S., Bourguignon, J.J., Wermuth, C.G. J. Med. Chem. (1999) [Pubmed]
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