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5-N-Arylaminothiazoles with pyridyl groups and their first-row transition metal complexes: synthesis, photophysical properties, and Zn sensing.

ABSTRACT: A series of 5-N-arylaminothiazoles were synthesized with facile diversity-oriented synthesis from readily available starting materials via the reaction of thioamide dianions and thioformamides. The introduction of various substituents at the 2-position of a thiazole ring (i.e., 2-pyridyl, 4-methylpyridyl, and phenyl groups) and on the nitrogen atom (i.e., p-tolyl and phenyl groups) significantly influenced the absorption and emission spectra of the isolated compounds. X-ray analysis confirmed that the substituents at the amino site were twisted from a thiazole ring, while the formation of its nickel complex showed dinuclear metal complexes bridged with chlorine atoms. Moreover, the formation of zinc-thiazole complexes showed enhanced emission properties in solution and noticeable emission in a solid state. In addition, thiazole-bridged dypyrromethene type ligands showed high selectivity toward Zn⁺², which make them good candidates for zinc sensing.

SUBMITTER: Puji Pamungkas KK

PROVIDER: S-EPMC9109715 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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5-N-Arylaminothiazoles with pyridyl groups and their first-row transition metal complexes: synthesis, photophysical properties, and Zn sensing.

Puji Pamungkas Khurnia Krisna KK Maruyama Toshifumi T Murai Toshiaki T

RSC advances 20220516 23

A series of 5-N-arylaminothiazoles were synthesized with facile diversity-oriented synthesis from readily available starting materials via the reaction of thioamide dianions and thioformamides. The introduction of various substituents at the 2-position of a thiazole ring (i.e., 2-pyridyl, 4-methylpyridyl, and phenyl groups) and on the nitrogen atom (i.e., p-tolyl and phenyl groups) significantly influenced the absorption and emission spectra of the isolated com ...[more]

PMID: 35702202

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Project description:Inflammatory mediators constitute a recently coined term in the field of metal-based complexes with antiplatelet activities. Our strategy targets Platelet-Activating Factor (PAF) and its receptor, which is the most potent lipid mediator of inflammation. Thus, the antiplatelet (anti-PAF) potency of any substance could be exerted by inhibiting the PAF-induced aggregation in washed rabbit platelets (WRPs), which internationally is a well-accepted methodology. Herein, a series of mononuclear (mer-[Cr(pqx)Cl3(H2O]) (1), [Co(pqx)Cl2(DMF)] (2) (DMF = N,N'-dimethyl formamide), [Cu(pqx)Cl2(DMSO)] (3) (DMSO = dimethyl sulfoxide), [Zn(pqx)Cl2] (4)) and dinuclear complexes ([Mn(pqx)(H2O)2Cl2]2 (5), [Fe(pqx)Cl2]2 (6) and [Ni(pqx)Cl2]2 (7)) incorporating the 2-(2'-pyridyl)quinoxaline ligand (pqx), were biologically evaluated as inhibitors of the PAF- and thrombin-induced aggregation in washed rabbit platelets (WRPs). The molecular structure of the five-co-ordinate analog (3) has been elucidated by single-crystal X-ray diffraction revealing a trigonal bipyramidal geometry. All complexes are potent inhibitors of the PAF-induced aggregation in WRPs in the micromolar range. Complex (6) displayed a remarkable in vitro dual inhibition against PAF and thrombin, with IC50 values of 1.79 μM and 0.46 μM, respectively. Within the series, complex (5) was less effective (IC50 = 39 μM) while complex (1) was almost 12-fold more potent against PAF, as opposed to thrombin-induced aggregation. The biological behavior of complexes 1, 6 and 7 on PAF's basic metabolic enzymatic pathways reveals that they affect key biosynthetic and catabolic enzymes of PAF underlying the anti-inflammatory properties of the relevant complexes. The in vitro cytotoxic activities of all complexes in HEK293T (human embryonic kidney cells) and HeLa cells (cervical cancer cells) are described via the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The results reveal that complex 3 is the most potent within the series.

Dataset Information

5-N-Arylaminothiazoles with pyridyl groups and their first-row transition metal complexes: synthesis, photophysical properties, and Zn sensing.

Publications

5-<i>N</i>-Arylaminothiazoles with pyridyl groups and their first-row transition metal complexes: synthesis, photophysical properties, and Zn sensing.

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