Synthesis, in vitro urease inhibitory activity and molecular docking of 3,5‐disubstituted thiadiazine‐2‐thiones

• Published in: Journal of heterocyclic chemistry Vol. 56; no. 11; pp. 3073 - 3080
• Main Authors: Shah, Muhammad Ishaq Ali, Khan, Rasool, Arfan, Mohammad, Wadood, Abdul, Ghufran, Mehreen
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc 01-11-2019
• Subjects: Chemical analysis; Infrared analysis; Jack beans; Molecular docking; NMR; Nuclear magnetic resonance
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.3705

A series of 3,5‐disubstituted‐tetrahydro‐thiadiazine‐2‐thione (1‐16) have been synthesized, characterized by elemental analysis, infrared (IR), UV‐visible, 1H NMR, 13C NMR, and MS spectroscopic techniques, and screened against jack bean urease. Among 16 compounds, compounds (1), (2), (3), (4), (6), (7), and (9) demonstrated excellent urease inhibitory activity with IC50 values (9.8 ± 0.5, 11.0 ± 0.6, 16.0 ± 1.5, 17.2 ± 0.5, 15.4 ± 0.5, 19.7 ± 0.4, and 15.8 ± 0.2μM), respectively, even better than the standard thiourea (IC50 = 21 ± 0.01μM). However, compound (8) shows an almost same level of inhibition (IC50 = 22.9 ± 0.3μM), as like standard. In this work, we reported for the first time urease inhibitory activity of thiadiazine thiones and its molecular docking studies.