Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies

Yasemin Ünver; Dilek ÜnlÜer; Şahin Dİrekel; Serdar DurdaĞi

doi:10.3906/kim-2004-78

Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies

Turk J Chem. 2020 Aug 18;44(4):1164-1176. doi: 10.3906/kim-2004-78. eCollection 2020.

Authors

Yasemin Ünver¹, Dilek ÜnlÜer¹, Şahin Dİrekel², Serdar DurdaĞi³

Affiliations

¹ Department of Chemistry, Faculty of Science, Karadeniz Technical University, Trabzon Turkey.
² Department of Medical Microbiology, Faculty of Medicine, Giresun University, Giresun Turkey.
³ Computational Biology and Molecular Simulations Laboratory, Department of Biophysics, School of Medicine,Bahçeşehir University, İstanbul Turkey.

Abstract

Since benzo [ b ] thiophene scaffold is one of the privileged structures in drug discovery as this core exhibitsactivities for different biological problems, in this study bis (benzo[ b ]thiophene-2-yl) alkyl methanimine derivatives (1-9) were synthesized by reacting benzo[ b ]thiophene-2-carbaldehyde with diamines. All newly compounds were characterized by IR, ¹H NMR and ¹³C NMR spectroscopic methods. Synthesized compounds were investigated using binary QSARbased models on therapeutic activity prediction of synthesized compounds and they showed high predicted activities in following diseases: bacterial, angina, allergy, depression and obesity. Thus, they were then tested for their antimicrobial and antileishmanial activities as a result of this theoretical study. Compound 1(N, N'- (propane-1,3-diyl) bis (1-(benzo [ b ] thiophene-2-yl)) methanimine) was found the most active compound in both diseases. Thus, its molecular docking studies were also carried out.

Keywords: Benzo [b] thiophene; Schiff base; antimicrobial and antileishmanial activities; binary QSAR models; molecular docking.