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Synthesis, in vitro urease inhibitory activity and molecular docking of 3,5‐disubstituted thiadiazine‐2‐thiones
Author(s) -
Shah Muhammad Ishaq Ali,
Khan Rasool,
Arfan Mohammad,
Wadood Abdul,
Ghufran Mehreen
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3705
Subject(s) - chemistry , thiourea , urease , in vitro , inhibitory postsynaptic potential , proton nmr , stereochemistry , docking (animal) , nuclear chemistry , carbon 13 nmr , medicinal chemistry , enzyme , organic chemistry , biochemistry , medicine , nursing , neuroscience , biology
A series of 3,5‐disubstituted‐tetrahydro‐thiadiazine‐2‐thione ( 1 ‐ 16 ) have been synthesized, characterized by elemental analysis, infrared (IR), UV‐visible, 1 H NMR, 13 C 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 IC 50 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 (IC 50 = 21 ± 0.01μM). However, compound ( 8 ) shows an almost same level of inhibition (IC 50 = 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.