2-(2-(Fluorosulfonyloxy)phenyl)benzoxazole

Nadezhda Danilenko,Andrei Khlebnikov,Vladimir Shmalyuk

doi:10.3390/m1242

Abstract

The fluorosulfate derivatives of benzoxazole attract attention since benzoxazole-based compounds have a wide range of biological activities, and the ability of the –SO2F group to react with various functional groups makes it possible to synthesize various new derivatives. The new 2-(2-(fluorosulfonyloxy)phenyl)benzoxazole (2) has been synthesized by the SuFEx click reaction in a two-chamber reactor. Compound 2 is the first example of a benzoxazole derivative with a fluorosulfate-containing substituent at position two of the benzoxazole heterocycle. The anti-cancer potency of 2 was evaluated in silico using molecular docking. The docking results suggest that title compound 2 is of great interest for further studies as a possible anaplastic lymphoma kinase inhibitor.

Highlights

June 2021Benzoxazole is one of the most important heterocyclic scaffolds which has found in many biologically active compounds
sulfur(VI) fluoride exchange (SuFEx) reaction is of scientific practical interest, since the key startingproceeds reagent SO
Despite aand fairly wideisrange of since known derivatives, little is known about the scientific practical interest, thebenzoxazole keyproceeds startingwith reagent

Summary

June 2021

Benzoxazole is one of the most important heterocyclic scaffolds which has found in many biologically active compounds. Benzoxazole derivatives have aand wideanalgesic range of effects dant, anti-ulcer, anticonvulsant, antihelmintic, antidepressant, biological activity, such as antitumor, antimicrobial, antiviral, antihistamine, antioxidant, Some important natural products, such as calcimycin, nakijinol, and boxazomycin A anti-ulcer, anticonvulsant, antihelmintic, antidepressant, and analgesic effects [1]. Benzoxaz naturally occurring benzoxazole derivatives, therecancer are compounds anti-cancer activity several human cancer cellcan linesbe [5]. Click reactions of sulfur (VI) fluoride exchange (SuFEx) have been successfully used for the synthesis of small molecules in chemical biology for labeling proteins and in material. For the synthesis of small molecules in chemical biology for labeling proteins and in mascience for obtaining polymeric materials and surface modification [7,8]. The aim of the present work was to obtain a new fluorosulfate benzoxazole derivatives

Resultsand and practical

F group

General Information and Compound 2 Synthesis

Molecular Docking

Conclusions