Computational Study of some Double Headed Acyclo-C-Nucleosides

Abstract

ABSTRACT. In the present paper we have a focus in a study of theoretical characterization of three double headed acyclo-C-nucleosides, which are a recent target of experimental studies. The structural and electronic properties of double headed acyclo-C-nucleosides, 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane-1,2,3,4-tetrol, 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol and 5,5'-(1,2,3,4-tetrahydroxybutane-1,4-diyl)bis(1,3,4-oxadiazole-2(3H)-thione), have been investigated theoretically by performing semi-empirical molecular orbital, ab initio Hartree-Fock (HF) and Density Functional Theory (DFT) calculations. Geometries of the three molecules are optimized at the level of Austin Model 1 (AM1). The electronic properties and relative energies of the molecules have been calculated by HF and DFT in the ground state.

Double-headed nucleosides: Synthesis and applications

“…All the double-headed nucleosides except derivative 242 showed moderate antibacterial activity in comparison with the known antibiotic combination amoxicillin/clavulanic acid (AMC) [20]. The structural and electronic properties of the double-headed nucleosides were explored theoretically by performing semiempirical molecular orbital, ab initio Hartree-Fock (HF), and density functional theory (DFT) calculations and their geometries were optimized at the level of Austin Model 1 (AM1) [104].…”

“…The structural and electronic properties of the double-headed nucleosides were explored theoretically by performing semi-empirical molecular orbital, ab initio Hartree–Fock (HF), and density functional theory (DFT) calculations and their geometries were optimized at the level of Austin Model 1 (AM1) [ 104 ].…”

DFT Studies of New Class of Single-Headed Nucleosides Derived from the D-glucaric Acid

“…However, we have selected three, which are : the 1,3,4-oxadiazole-2thione (5), the 1,2,4-triazole-3-thiol (6) and the 4-amino-1,2,4-triazole-3-thiol (7), whose structures are given in the figure 2. This choice is justified by the fact that three double-headed acyclo-C-nucleosides, carriers these heterocycles, were synthesized from the D-glucaric acid (1) (Amara and Othman, 2016) and whose computational results have already been published (Amara et al, 2015). So, this is continuity in the path of a series of molecules already synthesized.…”