Highly bioactive novel aryl-, benzyl-, and piperazine-selenoureas: synthesis, structural characterization and in vitro biological evaluation

Ziad Moussa; Ranem Kaddoura; Haythem A Saadeh; Nael Abutaha; Saleh A Ahmed

doi:10.1016/j.heliyon.2022.e10709

Highly bioactive novel aryl-, benzyl-, and piperazine-selenoureas: synthesis, structural characterization and in vitro biological evaluation

Heliyon. 2022 Sep 21;8(9):e10709. doi: 10.1016/j.heliyon.2022.e10709. eCollection 2022 Sep.

Authors

Ziad Moussa¹, Ranem Kaddoura¹, Haythem A Saadeh², Nael Abutaha³, Saleh A Ahmed^{4

5}

Affiliations

¹ Department of Chemistry, College of Science, United Arab Emirates University, P. O. Box 15551, Al Ain, United Arab Emirates.
² Department of Chemistry, School of Science, The University of Jordan, Amman 11942, Jordan.
³ Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh, Saudi Arabia.
⁴ Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia.
⁵ Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, Egypt.

Abstract

Selenoureas are widespread as useful elements for constructing important species and biologically active molecules. Finding an efficient and straightforward method to prepare this motif and biologically screen derivatives thereof is crucial. Herein, we demonstrate the effectiveness of using ethanol as a solvent in the preparation of various substituted aryl-, benzyl-, and piperazine-selenoureas from isoselenocyanates and amines. The synthetic method includes mild reaction conditions, large substrate scope, and good isolated yields. Biological evaluation of the prepared products on MDA-MB-231 and MCF-7 cancer cell lines revealed several remarkably active compounds (IC₅₀ < 10 μΜ) with the best one exhibiting IC₅₀ values of 1.8 μΜ and 1.2 μΜ observed against the challenging former triple-negative breast cancer cell line and the latter one, respectively. The chemical structures of all new compounds were fully characterized by multinuclear nuclear magnetic resonance (NMR) spectroscopy and high accuracy mass measurements.

Keywords: Isoselenocyanates; MCF-7; MDA-MB-231; Piperazine; Pyrimidine; Selenoureas.