Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives

A novel 6,8-dichloro [1,2,4]triazolo [3,4-b] [1,3]benzoxazole-3(2H)-thione 4 and its derivatives 5a and 5b are synthesized from 5,7-dichloro-2-hydrazinyl-1,3-benzoxazole 3, obtained by reaction of hydrazine hydrate with ethyl [(5,7-dichloro-1,3-benzoxazol-2-yl)sulfanyl]acetate 2. The newly synthesized compounds are characterized by analytical 1H NMR, 13C NMR, LC-MS mass spectrometry and elemental analysis. All synthesized compounds are screened for in vitro antioxidant and anthelmintic activities. In correlation to anthelmintic activity, compounds are subjected to molecular docking studies for the binding to β-Tubulin, target protein elite to the parasites.Compounds 3, 4 and 5a exhibited potential radical scavenging capacity with good anthelmintic activity. In molecular docking study also, compounds showed minimum binding energy and have good affinity toward the active pocket thus, they may be considered as good inhibitor of β-Tubulin.

Graphical abstractSeries of novel dichloro substituted benzoxazole-triazolo-thione derivatives were synthesized and screened for their in vitro antioxidant, anthelmintic activity and molecular docking studies with β-Tubulin.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Helminths infections are medical and public health problem both in humans and domestic animals. ► Anthelmintic drugs shows activity by binding selectively to β-Tubulin of nematodes and fluke. ► β-Tubulin is a protein subunit of microtubule and target protein elite to the parasites. ► All compounds are subjected to molecular docking studies to predict of β-Tubulin inhibition.