A new chemical space was generated via C2-functionalization of 3-arylbenzofurans. Mannich reaction of 3-arylbenzofurans with secondary amines and formaldehyde allowed for installation of aminomethyl unit at C2 position of benzofurans. A formyl group at C2 site introduced as a result of Vilsmeier-Haack formylation of 3-arylbenzofurans was employed as a reacting partner for three-component Kabachnik-Fields reaction with various amines and triethyl phosphite to give a wide variety of aminomethylphosphonates. Furthermore, several benzo[d]oxazoles and pyrrolo[1,2-a]quinoxalines were prepared by using the formyl group. Biological screening of the synthesized compounds revealed that the benzofuran bearing a pyrrolo[1,2-a]quinoxaline moiety (5b) most potently inhibited the viability of human blood cancer cells, but not solid tumor cells. Caspase activity assay, analysis of Annexin V-positive cells, and Western blot analysis indicated that 5b-induced death of human lymphoma U937 cells could result from its potential to induce the caspase-dependent apoptotic death of blood cancer cells with inhibition of ERK activation.
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All Science Journal Classification (ASJC) codes
- Organic Chemistry