Effect of bromine atom on the different tautomeric forms of microhydrated 5-bromouracil, in the DNA:RNA microhelix and in the interaction with human proteins

Abstract

Table S1. Calculated gas-phase relative energies (kJ/mol) of 5BrU tautomers U7, U8 and U10.

Synthesis and Biofunctional Properties of NaBr/H2O2‐Induced Brominated Uracil Derivatives

“…This methodology possesses the advantages of easily available reagents, short reaction time and simple procedure. The purified compounds were characterized using 1 H-NMR, 13 C-NMR and SC-XRD. Amongst all the screened derivatives, compounds 2 a and 2 b showed the most prominent antibacterial susceptibility towards gram-negative E. coli with IC 50 ~9.81 and 5.79 μg/mL, respectively.…”

“…Uracil and its halogenated derivatives, notably 5‐bromouracil, have been identified as promising agents against a new G6PD inhibitor that could be useful in biological applications. G6PD generates cellular nicotinamide adenine dinucleotide phosphate (NADPH), which is essential for producing fatty acids and cholesterol [13] . They have also been employed as intermediates for various synthetic modifications of related compounds with biological significance [14–16] …”

“…G6PD generates cellular nicotinamide adenine dinucleotide phosphate (NADPH), which is essential for producing fatty acids and cholesterol. [13] They have also been employed as intermediates for various synthetic modifications of related compounds with biological significance. [14][15][16] Therefore, developing a novel approach for synthesizing 5bromouracil derivatives under mild conditions has long been valued in synthetic transformations, pharmaceuticals, and agrochemicals.…”

DFT Study on tautomerism of cytosine and its 5-haloderivatives: A Review*

“…5-BrC can exist in various tautomeric forms as in Cy, with classical numbering of atoms: amino-oxo (C1), amino-hydroxy (C2a, C2b), imino (C3a, C3b) and (C4) 3H-oxo forms [19,20]. The most characteristic optimized geometric parameters of these tautomers are collected in Table 1, while the gas-phase relative energies are shown in Table 2.…”

“…It has been studied theoretically and experimentally by different authors [15][16][17]. Because of its medicinal importance, the molecular structure and vibrational spectra of this molecule has been previously analyzed in detail by us [18][19][20].…”