Syntheses of novel 1,5‐benzodiazepinederivatives: Crystal structures, spectroscopic characterizations, Hirshfeld surface analyses, molecular docking studies,DFTcalculations, corrosion inhibition anticipation, and antibacterial activities

Abstract

A series of newly pyrazolo‐1,5‐benzodiazepine derivatives (5‐7) was performed and characterized by using 1H, 13C‐NMR spectroscopic measurements. The molecular and crystal structures of two compounds 2 and 7 have also been further examined by single‐crystal X‐ray crystallography showing that the alkyl groups are beard by sulfur atom and to pyrazolic nitrogen atom in position 2 and not in position 1 of the tricyclic compounds as described in the literature. In addition, through Hirshfeld surface analysis, molecular docking studies, and DFT calculations, the closest contact between the active atoms of the compound can be determined. Also, the Monte Carlo simulations outcomes show that compounds 2 and 7 can be considered as a good acidic corrosion inhibitor for the aluminum metal, while emphasizing that the compound 7 provides enhanced prevention. Finally, compounds 1 to 7 were evaluated for their antibacterial activity against Gram‐positive and Gram‐negative microbial strains such as Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus. The results obtained demonstrated the antibacterial activity of compounds 1 to 7 tested using the minimal inhibitory concentration.

Crystal structure, Hirshfeld surface analysis and DFT calculations of (E)-3-[1-(2-hydroxyphenylanilino)ethylidene]-6-methylpyran-2,4-dione

“…Heterocyclic molecules play a very important role in life processes and are of major interest in the industrial development of dyes, pharmaceuticals, pesticides, and natural products (Saber et al, 2020;El Ghayati et al, 2021;Patra & Saxena, 2010). Therefore, scientists have devoted considerable effort to finding efficient synthetic methods for a wide variety of heterocyclic compounds (Yeh et al, 2014;Liaw et al, 2015).…”

Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid

“…The chemistry of heterocyclic compounds still receives increasing interest because of the therapeutic importance of most heterocyclic compounds, especially those with nitrogencontaining heterocycles, which are of great interest as potential bioactive molecules (Taia et al, 2020;Sebbar et al, 2016;El Ghayati et al, 2021;Dinakaran et al, 2012;Lahmidi et al, 2018;Hni et al, 2019). In this regard, pyrazolo [3,4-d]pyrimi-]pyrimidines are an important family of heterocyclic compounds, and their derivatives possess various pharmacological properties (Bakavoli et al, 2010;Severina et al, 2016), including their applications as anti-microbial (Holla et al, 2006;Bakavoli et al, 2010), anti-tumor (Kandeel et al, 2012), anti-inflammatory (El-Tombary, 2013), anti-oxidant (El-Mekabaty, 2015), anti-cancer (Gupta et al, 2008;Maher et al, 2019) and anti-convulsant (Severina et al, 2016) agents.…”

NiFe2O4@SiO2@PrNH2–DPA–CeCl3: a cerium-based magnetic nano dual-acid catalyst with high efficacy and recyclability for domino sequential synthesis of lactam ring-fused 1,5-benzodiazepines

“…[1][2][3][4] Among them, 1,5-bezodiazepines consisting of a benzene portion and a seven-member dinitrogen heteroatomic ring were regarded as prerogative motifs due to their surplus therapeutic function, such as antipsychotic, anticonvulsant, antiinflammatory and antimicrobial. [5][6][7][8] Recently, it has been confirmed that 1,5-benzodiazepines can unambiguously inhibit the HIV virus and various microbes. [9][10][11][12] The lactam ring also occupies an essential position in heterocyclic species, maintaining the antibacterial activity of certain compounds.…”