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Globally, the occurrence of skin cancers has been increasing day by day due to unprotected skin and exposure to UV radiation. This research is focused toward the evaluation of the antioxidant potential of an OH-free flavanone derivative that was synthesized by using 1,4-diazabicyclo[2.2.2]octane–polyethylene glycol (DABCO-PEG) 400. Ionic liquid was prepared via the alkylation of DABCO using 1-pentyl bromide followed by mixing with PEG 400. The structure of the synthesized molecules was characterized through single-crystal XRD. The target flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one, was subjected to free radical activity. In addition, in silico studies were carried out with proteins ribonucleotide reductase and tyrosinase and isobutyl containing flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one. The flavanone 2-(4-isobutylphenyl)chroman-4-one showed significant inhibition at a concentration of 25 μg/ml compared to vitamin C, which was also supported by the molecular docking studies. The flavanones exhibit binding energies of −6.45 and −6.83 kcal/mol for ribonucleotide reductase and tyrosinase, respectively. The results were further validated by molecular dynamic simulations, which recommended that further investigation of this flavanone must be carried out before using it in potent drug discovery in the field of skin cancer. [ABSTRACT FROM AUTHOR]

Here, a new (E)‐2‐(2‐chloro‐6‐fluorobenzylidene)hydrazinecarbothioamide hybrid 3 is reported for synthesis by using simple protocol. Compound was characterized, and its crystal structure was resolved by single crystal X‐ray analysis. The molecular structure showed perfect planarity with the 2,6‐halogen atoms disordered over the two positions. Hirshfeld surface (HS) analysis indicated H‐bonding and van der Waals interactions as leading intermolecular interactions in the crystal structure with most important contributions as H ... H (24.10%), H ... S/S ... H (20.80%) and H ... Cl/Cl ... H (13.50%). Density functional theory (DFT) analysis further highlighted on molecular orbital's energy transitions and comparison of absorption maxima with experimentally calculated λmax. Crystal was evaluated against elastase enzyme by using molecular docking and in vitro enzyme inhibition methods. An intuitive look at elastase inhibition demonstrated higher binding efficacy and lower IC50. Results from both studies have shown potent inhibitory activity of 3 against elastase. Kb and ΔG for 3‐DNA complex evaluated from molecular docking and UV/visible spectroscopy efficiently complemented each other, and the binding mode observed through docked structure was verified by viscometry. Theoretical and experimental investigations have provided evidence of substantial binding of the title compound with the DNA via intercalation. [ABSTRACT FROM AUTHOR]

A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reaction. This compound was further explored for its selectivity and sensitivity toward mercury (Hg2+) ions detection. Quantum chemical DFT calculations were performed to examine the adsorption of Hg(OOCCH3)2 on the surface of compound 7. The charge distributions before and after adsorption showed charge transfer from 7 to Hg(OOCCH3)2 which indicated that 7 was sensitive to Hg(OOCCH3)2 molecule for Hg+2 detection. The lowing in energy gap (ΔE), higher electrical conductivity and increased density of states (DOS) after Hg(OOCCH3)2 adsorption further depicted the potential of 7 as a chemical sensor for Hg+2 sensing. The photophysical potential of compound (7) was examined by employing a range of cations (Ba2+, Ca2+, Co2+, Hg2+, K+, Mg2+, Mn2+, Na+, NH4+ and Pd2+). A significant hyperchromic shift in compound 7 spectrum (UV/ and fluorescence) upon equimolar addition of Hg2+ ions indicated that the triazole-based compound (7) has exhibited selective interaction with Hg2+ ion in preference to other cations. The maximum chelation of compound (7) with Hg2+ was observed at pH 5.1 (slightly acidic medium). The compound (7) capability to recognize Hg2+ was observed even at 0.1 µM detectable limit, indicating greater sensitivity of 7 toward Hg2+. No significant effect of competitive metal ions on 7 – Hg2+ complex further authenticated robust selectivity and sensitivity of 7 toward sensing Hg2+ions. Binding mechanism indicated the formation of 2:1 complex of 7 - Hg2+. DFT and spectral findings complimented each other and proving the promising chemosensor candidacy of the compound 7 for Hg2+ ions. [ABSTRACT FROM AUTHOR]

The interest in the present study pertains to the development of a new compound based upon a benzimidazole thiourea moiety that has unique properties related to elastase inhibition, free radical scavenging activity and its DNA binding ability. The title compound, N -(4-(1 H -benzo[ d ]imidazol-2-yl)phenyl)-3-benzoyl thiourea (C 21 H 18 N 4 O 2 SH 2 O:TUBC), was synthesized by reacting an acid chloride of benzoic acid with potassium thiocyanate (KSCN) along with the subsequent addition of 4-(1 H -benzo[ d ]imidazol-2-yl)benzenamine via a one-pot three-step procedure. The structure of the resulting benzimidazole based thiourea was confirmed by spectroscopic techniques including FTIR, 1 H-NMR, 13 C-NMR and single crystal X-ray diffraction and further examined by Hirshfeld surface analysis. TUBC was also investigated by using both in silico methodology including molecular docking for elastase inhibition along with quantum chemical studies and in vitro experimental methodology utilizing elastase inhibition and free radical scavenging assay along with DNA binding experiments. Docking results confirmed that TUBC binding was within the active region of elastase. In comparison to the reference drug oleanolic acid, the low IC 50 value of TUBC also indicated its high tendency towards elastase inhibition. TUBC scavenged 80% of DPPH˙ radicals which pointed towards its promising antioxidant activity. TUBC-DNA binding by DFT, docking, UV-visible spectroscopy and viscosity measurements revealed TUBC to be a potential drug candidate that binds spontaneously and reversibly with DNA via a mixed binding mode. All theoretical and experimental findings pointed to TUBC as a potential candidate for a variety of biological applications., Competing Interests: The authors would like to declare that there is no established conflict of interest., (This journal is © The Royal Society of Chemistry.)