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Synthesis of a Novel Unexpected Cu(II)-Thiazolidine Complex-X-ray Structure, Hirshfeld Surface Analysis, and Biological Studies.

ABSTRACT: An unexpected trinuclear Cu(II)-thiazolidine complex has been synthesized by mixing CuCl₂·2H₂O with the Schiff base ligand, 1-(((4,5-dihydrothiazol-2-yl)ethylidene)hydrazono)methyl)phenol L, in ethanol. Unexpectedly, the reaction proceeded via the hydrolysis of the Schiff base L, followed by cyclization to afford 3-methyl-5,6-dihydrothiazolo[3,2-c][1,2,3]triazole (L^a), then complexation with the Cu(II) salt, forming the trinuclear [Cu₃(L^a)₄(Cl)₆] complex. The complex was characterized by means of FTIR spectra, elemental analysis, and X-ray crystallography. In the trinuclear [Cu₃(L^a)₄(Cl)₆] complex, there are two crystallographically independent hexa- and penta-coordinated Cu(II) sites, where the thiazolidine ligand L^a units act as a monodentate ligand and a linker between the Cu(II) centers. The crystal packing of the [Cu₃(L^a)₄(Cl)₆] complex is primarily affected by the weak non-covalent C-H∙∙∙Cl interactions. In accordance with Hirshfeld surface analysis, the Cl∙∙∙H, H∙∙∙H, S∙∙∙H, and N∙∙∙H percentages are 31.9%, 27.2%, 13.5%, and 9.9%, respectively. X-ray photoelectron spectroscopy confirmed the oxidation state of copper as Cu(II), as well as the presence of two different coordination environments around copper centers. The complex showed interesting antibacterial activity against the Gram-positive bacteria S. subtilis, with MIC = 9.7 µg/mL compared to MIC = 4.8 µg/mL for the control, gentamycin. Moreover, the Cu(II) complex showed an equal MIC (312.5 µg/mL) against C. albicans compared to ketoconazole. It also exhibits a very promising inhibitory activity against colon carcinoma (IC₅₀ = 3.75 ± 0.43 µg/mL).

SUBMITTER: Altowyan MS

PROVIDER: S-EPMC9319961 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Synthesis of a Novel Unexpected Cu(II)-Thiazolidine Complex-X-ray Structure, Hirshfeld Surface Analysis, and Biological Studies.

Altowyan Mezna Saleh MS Khalil Samar M S M SMSM Al-Wahaib Dhuha D Barakat Assem A Soliman Saied M SM Ali Ali Eldissouky AE Elbadawy Hemmat A HA

Molecules (Basel, Switzerland) 20220718 14

An unexpected trinuclear Cu(II)-thiazolidine complex has been synthesized by mixing CuCl2·2H2O with the Schiff base ligand, 1-(((4,5-dihydrothiazol-2-yl)ethylidene)hydrazono)methyl)phenol L, in ethanol. Unexpectedly, the reaction proceeded via the hydrolysis of the Schiff base L, followed by cyclization to afford 3-methyl-5,6-dihydrothiazolo[3,2-c][1,2,3]triazole (La), then complexation with the Cu(II) salt, forming the trinuclear [ ...[more]

PMID: 35889457

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Project description:The reaction of 4-hydroxyquinazoline (4HQZ) with aqueous solution of nitric acid afforded the corresponding quinazolinone-nitrate (4HQZN) complex in very good yield. The crystal structure of 4HQZN was determined and its structural and supramolecular structural aspects were analyzed. 4HQZN crystallized in the space group P21/c and monoclinic crystal system with one [4HQZ-H]+[NO3]- formula and Z = 4. Its supramolecular structure could be described as a 2D infinite layers in which the 4HQZN molecules are connected via N-H…O and C-H…O hydrogen bridges. Using DFT calculations, the relative stability of five suggested isomers of 4HQZN were predicted. It was found that the medium effects have strong impact not only on the isomers' stability but also on the structure of the 4HQZN. It was found that the structure of 4HQZN in DMSO and methanol matched well with the reported X-ray structure which shed the light on the importance of the intermolecular interactions on the isomers' stability. The structure of 4HQZN could be described as a proton transfer complex in which the nitrate anion acting as an e-donor whiles the protonated 4HQZ is an e-acceptor. In contrast, the structure of the isolated 4HQZN in gas phase and in cyclohexane could be described as a 4HQZ…HNO3 hydrogen bonded complex. Biological screening of the antioxidant, anticancer and antimicrobial activities of 4HQZ and 4HQZN was presented and compared. It was found that, 4HQZN has higher antioxidant activity (IC50 = 36.59 ± 1.23 µg/mL) than 4HQZ. Both of 4HQZ and 4HQZN showed cell growth inhibition against breast (MCF-7) and lung (A-549) carcinoma cell lines with different extents. The 4HQZ has better activity with IC50 of 178.08 ± 6.24 µg/mL and 119.84 ± 4.98 µg/mL, respectively. The corresponding values for 4HQZN are 249.87 ± 9.71 µg/mL and 237.02 ± 8.64 µg/mL, respectively. Also, the antibacterial and antifungal activities of 4HQZN are higher than 4HQZ against all studied microbes. The most promising result is for 4HQZN against A. fumigatus (MIC = 312.5 μg/mL).

Dataset Information

Synthesis of a Novel Unexpected Cu(II)-Thiazolidine Complex-X-ray Structure, Hirshfeld Surface Analysis, and Biological Studies.

Publications

Synthesis of a Novel Unexpected Cu(II)-Thiazolidine Complex-X-ray Structure, Hirshfeld Surface Analysis, and Biological Studies.

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