Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach

Azim Ziyaei Halimehjani; Faezeh Dehghan; Vida Tafakori; Elaheh Amini; Seyyed Emad Hooshmand; Yazdanbkhsh Lotfi Nosood

doi:10.1016/j.heliyon.2022.e09564

Synthesis of novel antibacterial and antifungal dithiocarbamate-containing piperazine derivatives via re-engineering multicomponent approach

Heliyon. 2022 May 30;8(6):e09564. doi: 10.1016/j.heliyon.2022.e09564. eCollection 2022 Jun.

Authors

Azim Ziyaei Halimehjani¹, Faezeh Dehghan¹, Vida Tafakori², Elaheh Amini³, Seyyed Emad Hooshmand⁴, Yazdanbkhsh Lotfi Nosood¹

Affiliations

¹ Faculty of Chemistry, Kharazmi University, 49 Mofateh St., 15719-14911, Tehran, Iran.
² Department of Cell and Molecular Biology, Faculty of Biological Sciences, Kharazmi University, Tehran, Iran.
³ Department of Animal Biology, Faculty of Biological Sciences, Kharazmi University, Tehran, Iran.
⁴ Department of Medical Nanotechnology, Faculty of Advanced Technologies in Medicine, Iran University of Medical Sciences, Tehran, Iran.

Abstract

A metal-free multicomponent synthetic route for the diverse preparation of dithiocarbamate-containing piperazine derivatives was developed through the C-N bond cleavage of DABCO ring. This multicomponent re-engineering approach proceeds via the reaction of amines, CS₂ and DABCO salts in one pot. Various DABCO salts and secondary amines are tolerated well in this protocol to afford a broad spectrum of dithiocarbamate-containing piperazines in good to high yields. Then, the selected compounds have been deployed against some critical types of bacteria and fungi. A certain number of synthesized compounds revealed not only appropriate antibacterial activity as investigated by disc fusion and minimum inhibitory concentration methods against bacteria (Gram-positive and Gram-negative), but also depicted good to excellent antifungal activity.

Keywords: Antibacterial; Antifungal; Dithiocarbamate; Multicomponent reactions; Piperazines.