A Swift One-Pot Solvent-Free Synthesis of Benzimidazole Derivatives and Their Metal Complexes: Hydrothermal Treatment, E
- PDF / 1,035,273 Bytes
- 11 Pages / 612 x 792 pts (letter) Page_size
- 66 Downloads / 162 Views
Swift One-Pot Solvent-Free Synthesis of Benzimidazole Derivatives and Their Metal Complexes: Hydrothermal Treatment, Enzymatic Inhibition, and Solubilization Studies M. B. Taja,b,*, A. Raheelc, W. Alelwanid, D. Hajjard, A. Makkid, A. M. Alnajeebid, N. A. Babteend, S. A. Tırmizic, and S. Noore,** a Department
of Chemistry, Islamia University, Bahawalpur, 63100 Pakistan of Chemistry, University of Sahiwal, Sahiwal, 57000 Pakistan c Department of Chemistry, Quaid-e-Azam University, Islamabad, 44000 Pakistan d Department of Biochemistry, College of Science, University of Jeddah, Jeddah, 80203 Saudi Arabia e Department of Chemistry, University of Agriculture, Faisalabad, 38000 Pakistan e-mail: *[email protected]; **[email protected] b Department
Received May 31, 2020; revised July 20, 2020; accepted August 5, 2020
Abstract—Three benzimidazole derivatives, 1-(1H-benzimidazol-2-yl)ethanol (HBE), 1H-benzimidazol2-yl(diphenyl)methanol (BDM) and 1,2-bis(1H-benzimidazol-2-yl)ethane-1,2-diol (BHBED), have been synthesized following the one-pot rapid green protocol. Complexes of benzimidazole derivatives with six 3d transition metals, Cu(II), Mn(II), Zn(II), Fe(II), Co(II), and Ni(II), have been synthesized by free hydrothermal method. The synthesized products have been characterized by FTIR, 1H, and 13C NMR, and mass spectroscopy, and CHN analysis, and 2:1 ligand to metal stoichiometry has been confirmed. The synthesized ligands and metal complexes have been tested for antioxidant potential (DPPH), inhibitory activity including inhibition of acetylcholinesterase (AChE), butyrylcholinesterase (BChE), lipoxygenase (LOX), α-glucosidase. Micellar solubilization of the metal complexes has been studied in sodium dodecyl sulphate (SDS) by UV-Vis spectroscopy and conductivity. The selected complexes of nickel, zinc and cobalt have demonstrated interaction with SDS, and the value of critical micellar concentration increased in all cases. Keywords: anionic surfactant, benzimidazole derivatives, hydrothermal treatment, inhibition activity, micellar solubilization, 3d metal complexation
DOI: 10.1134/S107036322008023X INTRODUCTION Benzimidazole drivatives have been explored as poisons in non-nucleoside topoisomerase-I and inhibitors of reverse transcriptase against HIV-1 and DNA-gyrase [1]. Benzimidazoles can act as ligands in binding with transition metals for experimental modelling in the biological systems [2–4]. Numerous routes to their synthesis, including the coupling of o-phenylenediamines with carboxylic acids [5], aldehydes [6] and o-esters under catalysis by Lewis acids [7] are reported. Phthalic acid attached to polymer-supported 4-fluoro-3-nitrobenzoic acid and polyethylene glycol ether in solid phase has been reported as a precursor for 2-substituted benzimidazoles, benzoxazoles and benzothiazoles [8]. High selectivity of transition metals, especially 3d, 4d, and 5d, stimulated
studies of their complexes biological and enzymatic activities [9]. However, synthetic approaches to such compounds are retarded by stringent
Data Loading...
