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).
Highlights
Urease is a metalloenzyme-containing nickel that frequently exists in various plants, bacteria, fungi, and algae and leads to the growing of different bacteria pathogen (e.g., Helicobacter pylori) in acidic condition inside the stomach
The structural feature of the desired hydroacridinone-based hydrazino-s-triazine was assigned based on sets of spectroscopic tools including FT-IR, mass spectroscopy (MS), nuclear magnetic resonance (NMR), and single-crystal X-ray diffraction technique
The 1 H-NMR spectra are consistent with the assigned structure of 4
Summary
Urease is a metalloenzyme-containing nickel that frequently exists in various plants, bacteria, fungi, and algae and leads to the growing of different bacteria pathogen (e.g., Helicobacter pylori) in acidic condition inside the stomach. In spite of numerous compounds being well-known to have potential urease inhibition, few of them are in the market for urease treatment. The discovery of effective and safe urease inhibitors is a very important issue in pharmaceutical research due to the contribution of ureases in different pathological conditions. Acridine-based compounds have been proven to display different pharmaceutical targets including anti-protozoal drugs [3], anti-bacterial drugs [4], anti-malarial agents [5], anti-HIV drugs [6], anti-inflammatory drugs [7], and antiviral drugs [8], and are known as cytotoxic agents and fluorescent probes [9,10]. Several acridine-based heterocyclic compounds have previously been reported to have a wide range of biological and therapeutic activities [11,12,13,14,15]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
