Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

Abstract

The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-s-triazine scaffold 4. Compound 4 was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-s-triazine is more active (IC50 = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC50 = 20.3 ± 0.43 µM).

Structural and theoretical study of (4E,5Z)‐4,5‐dibenzylidene‐1,2,3,6,7,8‐hexahydroacridine

“…The central fragment of the molecule is almost planar, the mean deviations of C(2) and C(7) atoms are 0.60 and 0.77 Å, respectively. The redistribution of bond lengths and bond angles in the central fragment correlates well with those of substituted 1,2,3,4,5,6,7,8‐octahydro acridine [9,10,16–19] and 1,8‐acridinones [20–24] reported previously. The H(14) atom is involved in an intramolecular C‐H…N contact to form a planar five‐membered ring (N…H(14)=2.376 Å, NH(14)C(14)=106.5°).…”

Design, Synthesis, Characterization and Computational Studies of Mannich Bases Oxadiazole Derivatives as New Class of Jack Bean Urease Inhibitors

“…Recently, several classes of compounds including hydroxamic acids, [16,17] phosphoramidites, [18] boronic and boric acids, [19] quinones, [20,21] heavy metal ions, [22] imidazoles, [23] and others have been investigated as urease inhibitors [24–30] . The bacterial ureases can also be inhibited by the five‐membered heterocycles like 1,2,4 triazoles and 1,3,4 oxadiazoles [30–35] .…”

“…[15] Recently, several classes of compounds including hydroxamic acids, [16,17] phosphoramidites, [18] boronic and boric acids, [19] quinones, [20,21] heavy metal ions, [22] imidazoles, [23] and others have been investigated as urease inhibitors. [24][25][26][27][28][29][30] The bacterial ureases can also be inhibited by the five-membered heterocycles like 1,2,4 triazoles and 1,3,4 oxadiazoles. [30][31][32][33][34][35] It is documented that some of the 1,3,4 oxadiazoles derived Mannich bases decrease inflammation and prevent fungal growth and they also possess analgesic, antiulcer, antibacterial, anti-HIV, anti-convulsant, anti-tuberculosis and anticancer activities and as inhibitors of various other enzymes and are used in many other applications.…”

Synthesis, combined theoretical and spectral characterization of some new 1,3,5 triazine compounds, and their in vitro biological analysis

“…These examples also reveal a range of applications. [16][17][18] For example, El-Faham et al designed and synthesized a variety of s-triazine hybrids with mono-/dipyrazolyl and piperidine moieties, which were then tested for cancer activity and toxicity in vivo. 19 Matthew A. Sanders et al have reported tri-substituted s-triazine as new lead compound TZ9 for selective RAD6B inhibitory activity and cellular anti-cancer activity.…”