Design, Synthesis, DFT Studies and Anticancer Activity of Novel Metal Complexes Containing 1,3,5-triazino[1,2-a]benzimidazole Moiety Using Microwave as an Approach for Green Chemistry

Hassan, Ali; Heakal, Bassem Hussen; Khamis, Hamdy; Hassan, Gamal Abdel Naeem; Marzouk, Emad; Abdelmoaz, Miral Ahmed; Younis, Ahmed

doi:10.21608/ejchem.2020.29618.2639

Design, Synthesis, DFT Studies and Anticancer Activity of Novel Metal Complexes Containing 1,3,5-triazino[1,2-a]benzimidazole Moiety Using Microwave as an Approach for Green Chemistry

Document Type : Original Article

Authors

¹ Al Azhar University

² Research Laboratory, Cairo Oil Refining Company, Mostorod, Qaliobia, Egypt

³ chemistry department, faculty of science, alazhar university

⁴ The city of Scientific Research and Technology Application, New Borg El-Arab Alexandria, Egypt.

⁵ Researcher chemist, Pwt International Company, Alexandria, Egypt.

⁶ Pharmaceutical Chemistry Department, Faculty of pharmacy, Sinai University E-mail address

⁷ Green Chemistry Department National Research Centre

10.21608/ejchem.2020.29618.2639

Abstract

2-(2-amino-4,10-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-4-yl)phenol (ligand) and its related metal complexes of Mn (II), Co (II), Ni (II), Cu (II) and Zn (II) were prepared under microwave irradiation. The structures of prepared compounds were elucidated in terms of elemental analysis, FT-IR, UV-Vis, 1HNMR, 13CNMR, EPR spectra and mass spectra in addition to magnetic studies at room temperature and thermal properties. Elemental analysis results determined mole ratios between the ligand and metal 1:1 or 1:2. The microwave approach provides clean, shorter reaction times and enhancements in yields. Coats Redfern and Horowitz Metzger equation were used to study Thermal kinetic parameters of dehydration and decomposition of the complexes. The geometries of the ligand and its Mn (II), Co (II), Cu (II) and Zn (II) complexes were optimized using Gaussian 09 W; density functional theory (DFT) B3LYP method. Also, the cytotoxic activity of the ligand and its metal complexes were evaluated against liver cancer cells (HepG-2) and the Cu (II) complex exhibited the highest cytotoxic activity with promising IC50 value = 3.5 µg/ml compared to standard reference cisplatin.

Keywords

Main Subjects