Nano‐synthesis and spectral, thermal, modeling, quantitative structure–activity relationship and docking studies of novel bioactive homo‐binuclear metal complexes derived from thiazole drug for therapeutic applications
Abstract:Seven novel homo-binuclear Cr(III), Fe(III), Cu(II), ZrO(II), Sn(II), Pb(II) and Ce(III) nanosized complexes of a thiazole drug (H 2 L) were synthesized for chemotherapeutic applications. H 2 L was prepared via a condensation reaction between 2-(4-aminobenzenesulfonamido)thiazole and 2-hydroxybenzaldehyde.The structures of H 2 L and its metal complexes were investigated by various means. These included microanalysis, 1 H NMR, 13 C NMR, Fourier transform infrared, UV-visible, electron spin resonance and mass sp… Show more
“…The far-IR spectra of both complexes exhibited the stretching vibrations of the ν(M-N) and ν(M-O) bonds at 633, 641 and 476, 462 cm À1 , respectively. [42] Based on the above results, the IR spectra data were in good agreement with the X-ray structural data.…”
Two novel complexes [Zn(L)2·(NO3)2] (1) and [Ni(L)2·2H2O]·2CH3OH·(NO3)2 (2) (L = 2‐(2‐thiazolyl)‐4‐methyl‐1,2‐dihydroquinazoline‐N3‐oxide) were synthesized successfully and characterized by elemental analysis, as well as various spectroscopic techniques. Specifically, the photoluminescence behavior of complex 1 was explored in different solvents. The structural characterization of both complexes has been determined single‐crystal X‐ray diffraction. It revealed that the metals in 1 and 2 are chelated by two L ligands in centro‐symmetrically fashion and the complexes are counterbalanced by nitrate ions which act as coordinating species in 1, while two water molecules complete the Ni coordination sphere in 2. In the crystal structures, the adjacent molecules of complex 1 disclosed a ladder‐like 2‐D network and 3‐D supramolecular self‐assembly. Simultaneously, an infinite 1‐D chain, 2‐D layered skeleton, and even meter‐shaped 3‐D network of 2 was governed by molecular interactions (H–bonds, C–H⋯π). Most strikingly, the research of antibacterial activity proved that two complexes had good activity against two standard bacteria strains. To ascertain deeply the optimum geometric configurations and detect the frontier molecular orbital energy gaps, density functional theory (DFT) calculations were also investigated. Additionally, analyses of Hirshfeld surfaces (HS) and electrostatic potential (ESP) were also performed to quantify the presence of diverse noncovalent interactions.
“…The far-IR spectra of both complexes exhibited the stretching vibrations of the ν(M-N) and ν(M-O) bonds at 633, 641 and 476, 462 cm À1 , respectively. [42] Based on the above results, the IR spectra data were in good agreement with the X-ray structural data.…”
Two novel complexes [Zn(L)2·(NO3)2] (1) and [Ni(L)2·2H2O]·2CH3OH·(NO3)2 (2) (L = 2‐(2‐thiazolyl)‐4‐methyl‐1,2‐dihydroquinazoline‐N3‐oxide) were synthesized successfully and characterized by elemental analysis, as well as various spectroscopic techniques. Specifically, the photoluminescence behavior of complex 1 was explored in different solvents. The structural characterization of both complexes has been determined single‐crystal X‐ray diffraction. It revealed that the metals in 1 and 2 are chelated by two L ligands in centro‐symmetrically fashion and the complexes are counterbalanced by nitrate ions which act as coordinating species in 1, while two water molecules complete the Ni coordination sphere in 2. In the crystal structures, the adjacent molecules of complex 1 disclosed a ladder‐like 2‐D network and 3‐D supramolecular self‐assembly. Simultaneously, an infinite 1‐D chain, 2‐D layered skeleton, and even meter‐shaped 3‐D network of 2 was governed by molecular interactions (H–bonds, C–H⋯π). Most strikingly, the research of antibacterial activity proved that two complexes had good activity against two standard bacteria strains. To ascertain deeply the optimum geometric configurations and detect the frontier molecular orbital energy gaps, density functional theory (DFT) calculations were also investigated. Additionally, analyses of Hirshfeld surfaces (HS) and electrostatic potential (ESP) were also performed to quantify the presence of diverse noncovalent interactions.
Two complexes [Zn(L) 2 (CH 3 OH) 2 ](NO 3 ) 2 (1) and [Ni(L) 3 ]Á(NO 3 ) 2 (2) (L = 2-[2-imidazolyl]-4-methyl-1,2-dihydroquinazoline-N 3 -oxide) were obtained successfully by means of slow evaporation solution technique (SEST)and characterized using elemental analysis, FT-IR, UV-vis, and fluorescence spectroscopic. X-ray diffraction revealed that the metal in complex 1 is chelated by two L ligands and two lattice methanol molecules, whereas in 2 by three L ligands, counterbalanced by nitrate ions. The crystal structures of both showed infinite 1-D, 2-D, and 3-D supramolecular architecture due to intermolecular interactions. Most strikingly, Zn (II) complex showed different fluorescence properties in diverse solvents. The antimicrobial activities of all compounds were compared and showed perceptible efficiency against Gramnegative and Gram-positive bacteria. Electrostatic potential (ESP) calculation was used to predict the nucleophilic and electrophilic attack sites. Density functional theory (DFT) calculation results showed good agreement with experimental data, as well as the frontier molecular orbital energy gaps were detected by time-dependent (TD)-DFT method with HOMO-LUMO calculations. Additionally, the non-covalent interactions of both complexes were further quantified and explored with the help of Hirshfeld surface analysis.
Single‐step synthesis of novel 4‐hydrazinothiazole derivatives 6a‐e was achieved under mild conditions via the sequential four components method using isothiocyanate, aminoguanidine, carbonyl adduct, and α‐haloketone derivatives. Deprotection of these hydrazinothiazoles was influenced by acylation, providing a novel group of diacylated molecular structures with a broader scope for the design of thiazolyl‐containing drugs 7a and 7b. FTIR, 1H/13C NMR, LC‐MS spectroscopy, and CHN elemental analyses have been used to study the compounds' chemical structures. Using an MTT assay on Human Periodontal Ligament Fibroblast (HPDLF) cells, the 4‐hydrazinothiazole derivatives were screened for cytotoxicity in an in vitro cytotoxicity investigation. The 4‐hydrazinothiazole compound 6b bearing an isopropylidene‐hydrazino group demonstrated a strongly potent cytotoxicity against CAKI1 (IC50 = 1.65±0.24 μM) and A498 (IC50 of 0.85±0.24 μM). Furthermore, the chloroacetyl‐containing thiazole compound 7a has displayed efficient inhibition of growth against the test cell lines CAKI1 and A498 at low micromolar IC50 of 0.78 and 0.74 μM, respectively.
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