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Synthesis and Structure Insights of Two Novel Broad-Spectrum Antibacterial Candidates Based on (E)-N'-[(Heteroaryl)methylene]adamantane-1-carbohydrazides.

  • Al-Wahaibi LH Department of Chemistry, College of Sciences, Princess Nourah bint Abdulrahman University, Riyadh 11671, Saudi Arabia.
  • Alvarez N Química Inorgánica, Facultad de Química, Universidad de la República, Av. General Flores 2124, Montevideo 11800, Uruguay.
  • Blacque O Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
  • Veiga N Química Inorgánica, Facultad de Química, Universidad de la República, Av. General Flores 2124, Montevideo 11800, Uruguay.
  • Al-Mutairi AA Department of Chemistry, College of Sciences, Al Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia.
  • El-Emam AA Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.
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  • 2020-04-26
Published in:
  • Molecules (Basel, Switzerland). - 2020
DFT
Hirshfeld surface analysis
IR
UV-Vis spectra
adamantane-1-carbohydrazides
antibacterial activity
crystal structure
English Two new N'-heteroarylidene-1-carbohydrazide derivatives, namely; E-N'-[(pyridine-3-yl)methylidene]adamantane-1-carbohydrazide (1) and E-N'-[(5-nitrothiophen-2-yl)methylidene]adamantane-1-carbohydrazide (2), were produced via condensation of adamantane-1-carbohydrazide with the appropriate heterocyclic aldehyde. Both compounds were chemically and structurally characterized by 1H-NMR, 13C-NMR, infrared and UV-vis spectroscopies, and single crystal X-ray diffraction. The study was complemented with density functional theory calculations (DFT). The results show an asymmetrical charge distribution in both compounds, with the electron density accumulated around the nitrogen and oxygen atoms, leaving the positive charge surrounding the N-H and C-H bonds in the hydrazine group. Consequently, the molecules stack in an antiparallel fashion in the crystalline state, although the contribution of the polar contacts to the stability of the lattice is different for 1 (18%) and 2 (42%). This difference affects the density and symmetry of their crystal structures. Both molecules show intense UV-Vis light absorption in the range 200-350 nm (1) and 200-500 nm (2), brought about by π → π* electronic transitions. The electron density difference maps (EDDM) revealed that during light absorption, the electron density flows within the π-delocalized system, among the pyridyl/thiophene ring, the nitro group, and the N'-methyleneacetohydrazide moiety. Interestingly, compounds 1 and 2 constitute broad-spectrum antibacterial candidates, displaying potent antibacterial activity with minimal inhibitory concentration (MIC) values around 0.5-2.0 μg/mL. They also show weak or moderate antifungal activity against the yeast-like pathogenic fungus Candida albicans.
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  • English
Open access status
gold
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https://sonar.ch/global/documents/48126
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