Beilstein J. Org. Chem.2021,17, 711–718, doi:10.3762/bjoc.17.60
derivative B22 which was treated with tetrabutylammonium fluoride (TBAF) in THF to obtain the hydroxy derivative C22. Compound C22 was converted to the sodium salt of A22 by using the procedure described for derivative A1. Analogously, compound A23 was prepared starting from 4-aminothiazole-2-carboxylic acid
PDF
Graphical Abstract
Scheme 1:
Synthesis of intermediate 1. Reagents and conditions: (i) trifluoroacetic anhydride, CH2Cl2, 0–35 °...
Beilstein J. Org. Chem.2009,5, No. 28, doi:10.3762/bjoc.5.28
a 2-aminopyridine group were recently designed and synthesized in our laboratory and were shown to have significant in vivo efficacy. In this work, analogs of our lead compound possessing 2- and 4-aminothiazole rings in place of the aminopyridine were synthesized. The less basic aminothiazole rings
potent than the 2-aminopyridine-based analogue. 4-Aminothiazoles were unstable in water, undergoing tautomerization and hydrolysis to give inactive thiazolones.
Keywords: 2-aminothiazole; 4-aminothiazole; nitric oxide synthase inhibitor; nNOS; Introduction
Neuronal nitric oxide synthase (nNOS) is the
followed by removal of the Boc groups (Scheme 5). Although the final deprotection did give the desired product, as evidenced by mass spectrometry, on addition of water, the product decomposed. The 4-aminothiazole tautomerized to the thiazoline, which was then hydrolyzed [20]. Test reactions on model 4
PDF
Graphical Abstract
Figure 1:
Lead compounds 1 and 2; 2- and 4-aminothiazole analogs 3 and 4a-c.