Síntese de benzoatos 3-(organocalcogenil)prop-2-in-1-ílicos catalisada por cobre: aplicação sintética e potencial farmacológico

Abstract

Due to the great relevance of benzoate and organochalcogen derivatives in pharmacology and, consequently, in organic synthesis, a methodology has been developed for the preparation of an unprecedented series of benzoates, containing organochalcogen groups (S, Se, Te) in their structures. After a range of experiments used to determine the best reaction condition, it was possible to obtain 3- (organochalcogenyl)prop-2-yn-1-yl benzoates by cross-coupling reaction of propargylic benzoates with diorganyl dichalcogenides under copper iodide(I)-catalyzed. The reactions proceeded at room temperature under air, without the use of base and using DMSO a solvent. The developed methodology proved to be efficient and versatile, leading to 19 examples, with yields that varied from 32 to 92%. To evaluate the synthetic applicability of the obtained the benzoates, the 3- (butylselenyl) prop-2-yn-1-yl benzoate was submitted to Suzuki and Sonogashira type reactions allowing to obtain seven 3-calcogenyl-benzoates prop-2-yn-1-yl in 42 to 87% yields. Also, the pharmacological potential of benzoate 3-(phenylselenyl)prop-2-yn-1-yl in cancer cells of the Human Glioblastoma A172 lineage was analyzed, observing a cellular reduction in concentrations of 50 and 100µM of the compound in one 24 hour time.