New s‐block complexes of 1,10‐phenanthroline and 1,3‐benzothizole‐2‐thiolate inhibit ureasein silicoandin vitro

Abstract

The coordination chemistry of 1,10‐phenanthroline (phen) and sodium 1,3‐benzothiazole‐2‐thiolate (SBT) with selected s‐block elements has been investigated. Four metal complexes were prepared and their structures were characterized using a variety of analytical techniques including infrared, UV–visible, 1H NMR and 13C NMR spectroscopies, elemental analysis, mass spectrometry and single‐crystal X‐ray diffraction. The reactions of phen and SBT with M(X)n (M = K(I), Cs(I), Mg(II), Sr(II); X = OH−, CO3−, Cl−; n = 1, 2) in MeOH–H2O yielded one‐dimensional chains of both potassium [K2(phen)2(BT)2(H2O)4]n (1) and caesium [Cs(phen)(BS)(H2O)]n (2) (where BT = 1,3‐benzthiazole‐2‐thiolate and BS = 1,3‐benzthiazole‐2‐sulfinothiolate) and mononuclear complexes of both magnesium {[Mg(phen)(H2O)4](BT)2·phen} (3) and strontium {[Sr(phen)2(H2O)4](BT)2} (4). In these complexes, phen binds via an N,N′ chelate pocket, while the monoanonic BT− ligands either coordinate in a bidentate fashion (in the case of 1) or remain uncoordinated (in the case of 3 and 4). In complex 2, SBT ligand was oxidized in situ into a new BS ligand. The sulfinothiolate oxygen atoms in BS coordinate with caesium in a tridentate fashion. Complexes 1–4 were evaluated against urease for enzyme inhibition. The complexes displayed significant inhibition with IC50 values in the range 10.8–45.8 μM. In order to examine the structure–activity relationship, the complexes were docked at the active site of urease. Docking results clearly demonstrate the binding of each complex within the active site of the enzyme.

Urease Inhibition and Structure‐Activity Relationship Study of Thiazolidinone‐, Triazole‐, and Benzothiazole‐Based Heterocyclic Derivatives: A Focus Review

“…Shah and coauthors [91] have synthesized four complexes of s‐block metals ( 23 ), namely K + , Cs + , Mg 2+ , Sr 2+ with 1,10‐phenanthroline (phen) and 1,3‐benzothizole‐2‐thiolate (SBT). The synthesized complexes were screened for their urease inhibitory potential against Canavalia ensiformis and the bioassay results revealed that the complexes of Mg 2+ ( 23 c ) and Sr 2+ ( 23 d ) displayed superior urease inhibition potential with an IC 50 value of 10.8 and 13.8 μM, respectively, compared with the reference inhibitors, thiourea (IC 50 =20.8 μM) while that of Cs + ( 23 b ) exhibited poor activity (IC 50 =45.8 μM).…”

“…Özil and coauthors [62] synthesized and tested antiurease potency of two series of benzothiazole-based scaffolds, namely; Shah and coauthors [91] have synthesized four complexes of s-block metals (23), namely K + , Cs + , Mg 2 + , Sr 2 + with 1,10phenanthroline (phen) and 1,3-benzothizole-2-thiolate (SBT).…”

Synthesis, crystal structures, DNA interactions, and antitumor activity of two new dinuclear copper(ii) complexes with thiazole ligand

“…30 The selection of ligand plays an important role in the biological activity of complexes. 31 Thiazole derivatives, due to their electron donation properties with their nitrogen-containing heterocyclic, are commonly used as dinuclear 32,33 or mononuclear 34 ligands to synthesize multi-functional thiazole metal complexes with transition metal. 35,36 Thiazole metal complexes are widely used in medicine, 37 optical materials, 38 and agriculture.…”