Synthesis, crystal structure, DFT studies, Hirshfeld surface analysis and drug delivery performance of bis(2-chloro-4,6-diaminopyrimidine)copper(II)-dichloride

Yağcı, Nermin Kahveci; Kansız, Sevgi; Özcandan, Eda

doi:10.1016/j.molstruc.2021.131142

Cited by 20 publications

(7 citation statements)

References 36 publications

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“… 48 , 49 This method has received special attention in recent years, as it allows an accurate and complete understanding of intermolecular interactions. 50 − 56 The Hirshfeld surface is defined as based on the normalized contact distance ( d norm ) given by eq 9 . To recognize the interatomic contacts, a red, blue, and white color scheme is used, representing the Hirshfeld surface calculated from the d norm .…”

Section: Resultsmentioning

confidence: 99%

“…Using Hirshfeld surface (HS) analysis and fingerprint plots (FPs) are frequently used methods to analyze the contribution and percentage of distinct intermolecular interactions to the crystal packing. , This method has received special attention in recent years, as it allows an accurate and complete understanding of intermolecular interactions. − The Hirshfeld surface is defined as based on the normalized contact distance ( d norm ) given by eq . To recognize the interatomic contacts, a red, blue, and white color scheme is used, representing the Hirshfeld surface calculated from the d norm .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide

et al. 2022

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In this study, a novel heterocyclic amide derivative, N -(3-cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide ( I ), was obtained by reacting 2-aminothiophene-3-carbonitrile with activated 2-(thiophen-2-yl)acetic acid in a N -acylation reaction and characterized by elemental analyses, FT-IR, 1 H and 13 C NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C–H···N and N–H···N hydrogen bonds. In addition, I was investigated computationally using the density functional theory (DFT) method with the B3LYP exchange and correlation functions in conjunction with the 6311++G(d,p) basis set in the gas phase. Fukui function (FF) analysis was also carried out. Electrophilicity-based charge transfer (ECT) method and charge transfer (Δ N ) were computed to examine the interactions between I and DNA bases (such as guanine, thymine, adenine, and cytosine). The most important contributions to the Hirshfeld surface are H···H (21%), C···H (20%), S···H (19%), N···H (14%), and O···H (12%). An ABTS antioxidant assay was used to evaluate the in vitro antioxidant activity of I . The compound exhibited moderate antioxidant activity. The antimicrobial activity of the title molecule was investigated under aseptic conditions, using the microdilution method, against Gram-positive and Gram-negative bacterial strains, and it also demonstrated significant activity against yeasts ( Candida glabrata ATCC 90030, Candida krusei ATCC 34135). The findings revealed that the molecule possesses significant antioxidant and antimicrobial properties.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide

et al. 2022

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“…The results are outlined in Table 4 in addition to being displayed in Figure S3. The 1 H NMR spectrum of L revealed at a chemical shift of 8.95 ppm for the -N=CH azomethine group, at 6.96-7.94 ppm for the -CH aromatic group and the signal observed at a chemical shift of 13.09 ppm can be credited to the presence of the phenolic hydroxyl group [52][53][54]. Based on the observation of the proton (OH) for the phenolic group in the spectra of the chelates and its chemical shift, it is suggested that L interacts via the oxygen atom of the proton in the phenolic group.…”

Section: Nuclear Magnetic Resonancementioning

confidence: 93%

First Report on Several NO-Donor Sets and Bidentate Schiff Base and Its Metal Complexes: Characterization and Antimicrobial Investigation

et al. 2023

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The condensation product of the reaction between aniline and salicylaldehyde was a 2-(2-hydroxybenzylidinemine)—aniline Schiff base bidentate ligand (L). L was used to generate complexes by interacting with the metal ions lanthanum(III), zirconium(IV), yttrium(III), and copper(II), in addition to cobalt(II). Various physicochemical techniques were utilized to analyze the synthesized L and its metal chelates, including elemental analysis (CHN), conductimetry (Λ), magnetic susceptibility investigations (μeff), Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H NMR) spectroscopy, ultraviolet–visible (UV-Vis.) spectrophotometry, and thermal studies (TG/DTG). FT-IR revealed that the L molecule acted as a bidentate ligand by binding to metal ions via both the oxygen atom of the phenolic group in addition to the nitrogen atom of the azomethine group. Additionally, 1H NMR data indicated the formation of complexes via the oxygen atom of the phenolic group. An octahedral geometrical structure for all of the chelates was proposed according to the UV-Vis. spectra and magnetic moment investigations. Thermal analysis provided insight into the pattern of L in addition to its chelates’ breakdown. In addition, the investigation furnished details on the chelates’ potential chemical formulas, the characteristics of adsorbed or lattice H2O molecules, and the water that is coordinated but separated from the structure at temperatures exceeding 120 °C. The thermodynamic parameters utilizing Coats–Redfern in addition to Horowitz–Metzger equations were studied. The antimicrobial effectiveness of L and its chelates against distinct species of bacteria and fungi was studied using the disc diffusion method. Cu(II) and Y(III) chelates had significant antimicrobial activity against Staphylococcus aureus and Micrococcus luteus.

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“…The intermolecular interactions are represented using different colors, like red, blue and white scheme, indicating Hirshfeld surface calculated from the d norm . The red spots show the shortest contacts, that is, closer than the sum of the van der Waals radii, white color indicating distances near the van der Waals radii separation while the blue spots shows the longer contacts, that is, distances longer than the van der Waals radii (Al‐Resayes et al, 2020; Yağcı et al, 2021). The Hirshfeld surface mapped on the [Ru(Bpy) 3 ] 2+ cations of RBMN and RBMS structures and surface properties, such as, d norm , shape index, curvedness, and fragment patch were determined.…”

Section: Methodsmentioning

confidence: 99%

Structure‐based biological investigations on ruthenium complexes containing 2,2′‐bipyridine ligands and their applications in photodynamic therapy as a potential photosensitizer

Puttaswamy,

Mahanta,

Sarma

et al. 2023

Chem Biol Drug Des

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Ruthenium complexes have been investigated for various biological applications by virtue of their radical scavenging, DNA binding, receptor binding, and cytotoxic abilities; especially the possible potential application of these complexes in photodynamic therapy (PDT). This study focuses on the synthesis, structural characterization and biological application (pertaining to its cytotoxicity and radical generation) of ruthenium complexed with salicylaldehyde fumaryl‐dihydrazone (slfhH4), salicylaldehyde glutaryl‐di‐hydrazone (slfgH4) and 2,2′‐bipyridine (bpy). During the synthesis, the anticipated complex was precipitated out but as serendipity, Ruthenium(II) tris (2,2′‐bipyridyl) monochloride nonahydrate {[Ru(bpy)3]2+.Cl.9H2O} (RBMN) and Ruthenium(II) tris (2,2′‐bipyridyl) monochloride septahydrate {[Ru(bpy)3]2+.Cl.7H2O}(RBMS) were crystallized from the filtrate. The crystal structure of complexes RBMN and RBMS were determined by a single‐crystal X‐ray diffraction methods and it showed that chlorine anion lies at the crystallographic axis and forms a halogen hydrogen‐bonded organic framework (XHOF) to provide the stability. In comparison with similar structures in Cambridge Crystallographic Data Center (CCDC) revealed that the nature of the XHOF framework and the layered packing are conserved. The compounds showed excellent cytotoxic ability (against L6 cells) and the nitro blue tetrazolium (NBT) assay upon irradiation to light revealed its ability to produce reactive oxygen species (ROS). The presence of partially occupied water molecules in the layered organization within the crystal packing mimics the release of ROS resulting in cytotoxicity. The structural results together with the biological data make these complexes interesting candidates for potential photosensitizers for PDT applications.

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Synthesis, crystal structure, DFT studies, Hirshfeld surface analysis and drug delivery performance of bis(2-chloro-4,6-diaminopyrimidine)copper(II)-dichloride

Cited by 20 publications

References 36 publications

Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide

Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide

First Report on Several NO-Donor Sets and Bidentate Schiff Base and Its Metal Complexes: Characterization and Antimicrobial Investigation

Structure‐based biological investigations on ruthenium complexes containing 2,2′‐bipyridine ligands and their applications in photodynamic therapy as a potential photosensitizer

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