Acta Chimica Slovaca (ACS) publishes papers on fundamental and applied aspects of chemistry, biochemistry, chemical technology, chemical engineering and process control, biotechnology and food technology. Welcome are also topics which include chemical aspects of materials, physical chemistry and chemical physics, analytical chemistry, macromolecular chemistry and biomedical engineering.

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

Július Sivý *, Dušan Bortňák a, Daniel Végh b, Erik Rakovský c

Faculty of Mechanical Engineering, STU, Námestie slobody 17, Bratislava 1, SVK-812 31, Slovak Republic
a Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, STU, Radlinského 9, Bratislava 1, SVK-812 37, Slovak Republic
b Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, STU, Radlinského 9, Bratislava 1, SVK-812 37, Slovak Republic
c Department of Inorganic Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovičova 6, Bratislava 4, SVK-842 15, Slovak Republic

E-mail: * julius.sivy@stuba.sk

Abstract: Two novel potent perfluorophenylhydrazone derivatives as multitarget 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), presented that potentially could be improved by further design. Their multitarget structures and features have been combined as potential AD therapeutics. The crystals (I), and (II), are molecules with two rings and hydrazone part like a centre of the molecule. The compounds have been synthesized and characterized by elemental, spectroscopic (1H-NMR) analysis. The crystal structures of the solid phase were determined by single crystal X-ray diffraction method. They crystallize in the monoclinic space group with Z = 4 and Z = 2 molecules per unit-cell. The compound (I) crystallizes as a racemate in the centrosymmetric space group and the compound (II) crystallizes as a non-racemate in the non-centrosymmetric space group. The “absolute configuration and conformation for bond values” were derived from the anomalous dispersion (rmad) for (II). The crystal structures are revealed diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring···π-ring, C-H···π-ring and they were investigated. The expected stereochemistry of hydrazones atoms C7, N2 and N1 were confirmed for (I) and (II). The hole molecule of the (I), and (II) possesses “a boat conformation” like a 6-membered ring. The results of the single crystal studies are reproduced with the help of Hirshfeld surface study and Gaussian software.

Keywords: Ab initio DFT/B3LYP/6-311G/Auto calculation, hydrazine, Hirshfeld surface, hydrogen interactions, single-crystal X-ray study

Acta Chimica Slovaca, Vol. 16, No. 1, 2023, pp. 81—91, DOI: 10.2478/acs-2023-0008