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Two potent novel perfluorophenylhydrazone derivatives are presented as multi-target compounds to combat Alzheimer disease C11H4BrF5N2S, 1-((4-bromothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (I) and C12H6BrF5N2S, 1-((4-bromo-5-methylthiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (II), which can potentially be improved by further design. Their multi-target structures and features have been combined as potential AD therapeutics. Crystals (I), and (II), are molecules with two rings and a hydrazone part as a centre of the molecule. The compounds have been synthesised and characterised by elemental spectroscopic (1H-NMR) analysis. Crystal structures of the solid phase were determined by single crystal X-ray diffraction method. Both compounds crystallise in the monoclinic space group with <italic>Z</italic> = 4 and <italic>Z</italic> = 2 molecules per unit-cell. Compound (I) crystallises as a racemate in the centrosymmetric space group and compound (II) crystallises as a non-racemate in the non-centrosymmetric space group. Their “absolute configuration and conformation for bond values” were derived from the anomalous dispersion (rmad) for (II). Crystal structures revealed diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring…<italic>π</italic>-ring, C—H…<italic>π</italic>-ring. The expected stereochemistry of hydrazones atoms C7, N2 and N1 were confirmed for (I) and (II). Both molecules show “boat conformation” like a 6-membered ring. Results of single crystal studies were reproduced with the help of Hirshfeld surface study and Gaussian software.
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Two potent novel perfluorophenylhydrazone derivatives are presented as multi-target compounds to combat Alzheimer disease C11H4BrF5N2S, 1-((4-bromothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (I) and C12H6BrF5N2S, 1-((4-bromo-5-methylthiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (II), which can potentially be improved by further design. Their multi-target structures and features have been combined as potential AD therapeutics. Crystals (I), and (II), are molecules with two rings and a hydrazone part as a centre of the molecule. The compounds have been synthesised and characterised by elemental spectroscopic (1H-NMR) analysis. Crystal structures of the solid phase were determined by single crystal X-ray diffraction method. Both compounds crystallise in the monoclinic space group with Z = 4 and Z = 2 molecules per unit-cell. Compound (I) crystallises as a racemate in the centrosymmetric space group and compound (II) crystallises as a non-racemate in the non-centrosymmetric space group. Their “absolute configuration and conformation for bond values” were derived from the anomalous dispersion (rmad) for (II). Crystal structures revealed diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring…π-ring, C—H…π-ring. The expected stereochemistry of hydrazones atoms C7, N2 and N1 were confirmed for (I) and (II). Both molecules show “boat conformation” like a 6-membered ring. Results of single crystal studies were reproduced with the help of Hirshfeld surface study and Gaussian software.

Two novel potent perfluorophenylhydrazone derivatives, 1-((4-bromothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, and 1-((4-bromo-5-methylthiophen-2-yl)methylene)-2-(perfluorophenyl)hydrazine as multi-target compounds to combat Alzheimer disease and their crystal, molecular, and electronic properties

Department of Inorganic Chemistry, Faculty of Natural Sciences

Acta Chimica Slovaca

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Two potent novel perfluorophenylhydrazone derivatives are presented as multi-target compounds to combat Alzheimer disease C11H4BrF5N2S,...

Data publikacji: 15 gru 2023

Zakres stron: 81 - 91

DOI: https://doi.org/10.2478/acs-2023-0008

Słowa kluczowe
DFT/B3LYP/6-311G/Auto calculation, hydrazine, Hirshfeld surface, hydrogen interactions, single-crystal X-ray study

© 2023 Július Sivý et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Data publikacji: 15 gru 2023

Zakres stron: 81 - 91

DOI: https://doi.org/10.2478/acs-2023-0008

Słowa kluczoweDFT/B3LYP/6-311G/Auto calculation, hydrazine, Hirshfeld surface, hydrogen interactions, single-crystal X-ray study

© 2023 Július Sivý et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Słowa kluczowe
DFT/B3LYP/6-311G/Auto calculation, hydrazine, Hirshfeld surface, hydrogen interactions, single-crystal X-ray study