3 years ago

Synthesis and Anti-inflammatory Evaluation of 2-Aminobenzaldehydes via Ir(III)-Catalyzed C–H Amidation of Aldimines with Acyl Azides

Synthesis and Anti-inflammatory Evaluation of 2-Aminobenzaldehydes via Ir(III)-Catalyzed C–H Amidation of Aldimines with Acyl Azides
Hyo Sun Suh, Hyung Sik Kim, Soo Bong Han, Neeraj Kumar Mishra, In Su Kim, Prashant Chakrasali, Byung Mu Lee, Sang Hoon Han, Taeyoung Kim, Saegun Kim
The aldimine-directed C–H amidation of various arenes with N-acyl azides as amidation surrogates under cationic iridium(III) catalysis is described. This transformation efficiently provides a range of 2-aminobenzaldehyde derivatives with excellent site selectivity and functional group compatibility. The resulting 2-aminobenzaldehyde framework provides facile access to a range of biologically interesting heterocycles. In addition, all synthetic compounds were screened for anti-inflammatory activity against interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) with lipopolysaccharide (LPS)-induced RAW264.7 cells. Generally, a range of ortho-amidated benzaldehydes displayed promising inhibitory activity against IL-1β and TNF-α compared to dexamethasone as a positive control. Notably, compounds (3ae and 4ac) were found to exhibit potent anti-inflammatory activity stronger than that of dexamethasone.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01280

DOI: 10.1021/acs.joc.7b01280

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