Sonochemical thiocyanation of pyrrolo [1, 2-a] quinoxalines: Identification of potential inhibitors of SIRT1

15 12 2024

Authors: Mallesham Baldha, Jyothi Shivanoori, Sunder Kumar Kolli, Ravikumar Kapavarapu, Manojit Pal

A series of compounds based on the 1-thiocyanatopyrrolo[1,2-a]quinoxaline framework were designed and assessed as potential inhibitors of SIRT1. A convenient access to this class of compounds was achieved via the sonochemical thiocyanation of pyrrolo[1,2-a]quinoxalines. The methodology involved use of N-thiocyanatosaccharin as a key agent under mild reaction conditions. The reaction proceeded with high regioselectivity affording the desired compounds in good to acceptable yields. The in silico docking studies suggested good interactions of these compounds with SIRT1 when majority of them formed an H-bond with GLN 345 though the most promising 3h formed H-bond with ILE347. The thiocyanato (NCS-) group of these compounds seemed to have played a key role in their interactions that formed either an H-bond through its nitrogen atom and/or participated in a pi-sulfur interaction via its sulfur atom …