RESUMO
A concise two one-pot synthesis of WINâ 64821, eurocristatine, 15,15'-bis-epi-eurocristatine, ditryptophenaline, ditryptoleucineâ A, WINâ 64745, cristatuminâ C, asperdimin, naseseazineâ A, and naseseazineâ B is detailed, based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and a one-pot procedure for the construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10 up to 27 %. In addition, 1'-(2-phenylethylene)-ditryptophenaline was synthesized by using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific proteaseâ 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan-based dimeric diketopiperazine alkaloids discovered 15,15'-bis-epi-eurocristatine, 1'-(2-phenylethylene)-ditryptophenaline, and WINâ 64745 as new drug candidates.