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2-Aminothiazoles as Therapeutic Leads for Prion Diseases

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† The Small Molecule Discovery Center
‡ The Institute for Neurodegenerative Diseases
§ Department of Pharmaceutical Chemistry
∥ Department of Neurology
University of California, San Francisco, MC2552 Byers Hall 503D, 1700 4th Street, San Francisco, California 94158, United States
*To whom correspondence should be addressed. Phone: (415) 514-9698. Fax: (415) 514-4507. E-mail: [email protected]
Cite this: J. Med. Chem. 2011, 54, 4, 1010–1021
Publication Date (Web):January 19, 2011
https://doi.org/10.1021/jm101250y
Copyright © 2011 American Chemical Society
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    Abstract

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    2-Aminothiazoles are a new class of small molecules with antiprion activity in prion-infected neuroblastoma cell lines ( J. Virol. 2010, 84, 3408). We report here structure−activity studies undertaken to improve the potency and physiochemical properties of 2-aminothiazoles, with a particular emphasis on achieving and sustaining high drug concentrations in the brain. The results of this effort include the generation of informative structure−activity relationships (SAR) and the identification of lead compounds that are orally absorbed and achieve high brain concentrations in animals. The new aminothiazole analogue (5-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine (27), for example, exhibited an EC50 of 0.94 μM in prion-infected neuroblastoma cells (ScN2a-cl3) and reached a concentration of ∼25 μM in the brains of mice following three days of oral administration in a rodent liquid diet. The studies described herein suggest 2-aminothiazoles as promising new leads in the search for effective therapeutics for prion diseases.

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    Synthetic schemes for new 2-aminothiazole analogues 4−50 and synthetic intermediates 51−70. Triplicate data set for compounds 3−50 in the ScN2a-cl3 dividing cell assay (EC50 and pEC50 values), standard deviation (SD), and percent coefficient of variation (CV) values. Mean values (three determinations) for 3−50 in the ScN2a-cl3 nondividing cell assay and calcein-AM cell viability assay. 1D NOESY data that supports the assigned site of methylation and acylation for compounds 49 and 50, respectively. This material is available free of charge via the Internet at http://pubs.acs.org.

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