2-Aminooxazoles and their derivatives (review)

A Modified Approach to 2-(N-Aryl)-1,3-oxazoles: Application to the Synthesis of the IMPDH Inhibitor BMS-337197 and Analogues

“…

A modified approach to the synthesis of 2-(N-aryl)-1,3-oxazoles, employing an optimized iminophosphorane/heterocumulene-mediated methodology, and its application to the synthesis of BMS-337197, a potent inhibitor of IMPDH, are described.The 2-amino-1,3-oxazole moiety is associated with a broad spectrum of biological activity, e.g., antifungal, antibacterial, and antiviral. 1 We recently reported on the identification of BMS-337197 as a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH). 2 The central 2-amino-1,3-oxazole moiety is the key structural element in BMS-337197.

…”

“…The 2-amino-1,3-oxazole moiety is associated with a broad spectrum of biological activity, e.g., antifungal, antibacterial, and antiviral. 1 We recently reported on the identification of BMS-337197 as a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH). 2 The central 2-amino-1,3-oxazole moiety is the key structural element in BMS-337197.…”

“…The ethyl acetate layer was dried over sodium sulfate and purified using silica gel column chromatography (hexane/ethyl acetate) to yield the title compound (2.1 g, 95%). 1 H NMR (DMSO-d6): δ 10.7 (s, 1H), 8.35 (s, 1H), 7.00-7.8 (m, 9H), 4.4 (d, J ) 15 Hz, 1H), 4.1 (d, J ) 15 Hz, 1H), 3.9 (s, 3H), 3.1 (s, 3H), 2.0 (s, 3H). HRMS (ESI) calcd for C26H27N5O5 (M + H) + 490.2091, found 490.2087.…”

Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles

“…Heterocycles bearing a 2-amino-1,3-oxazole moiety demonstrate a wide spectrum of biological activity such as antiviral (HIV-1), enzyme (VEGFR2, inosine monophosphate dehydrogenase), and valosin-containing protein inhibition. They behave as TRPV1 receptor antagonist and also as antihelminthic, diuretic, and fungicidal active compounds . Synthetic approaches toward substituted 2-amino-1,3-oxazoles are rather limited. , …”