Chalcone- and flavone-based novel terpyridine metal complexes: Synthesis, electrochemical, photophysical, photovoltaic and computational studies

Mughal, Ehsan Ullah; Obaid, Rami J.; Sadiq, Amina; Alsharif, Meshari A.; Naeem, Nafeesa; Kausar, Samia; Altaf, Ataf Ali; Jassas, Rabab S.; Ahmed, Safeer; Alsantali, Reem I.; Ahmed, Saleh

doi:10.1016/j.dyepig.2022.110248

Cited by 11 publications

(6 citation statements)

References 54 publications

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“…S3, S5 and S7), a singlet signal is seen at 8.750-8.738 ppm due to the magnetically equivalent protons H3 0 and H5 0 , while in the 1 H NMR spectra of the coordination complexes, this singlet signal has shifted to higher values of � (low field) in the range 10.4-9.63 ppm. This behaviour suggests the formation of the proposed coordination complexes, which indicates the strong interactions generated between metal and ligand (Mughal et al, 2022). In general, the observed signals for the complexes are displaced to a low field due to an electron-deficient metal cation in the structure.…”

Section: Uv-vis Spectrophotometrymentioning

confidence: 84%

Synthesis, characterization and structural analysis of complexes from 2,2′:6′,2′′-terpyridine derivatives with transition metals

Fajardo,

Arteaga,

Ellena

et al. 2024

Acta Crystallogr C

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The synthesis and structural characterization of three families of coordination complexes synthesized from 4′-phenyl-2,2′:6′,2′′-terpyridine (8, Ph-TPY), 4′-(4-chlorophenyl)-2,2′:6′,2′′-terpyridine (9, ClPh-TPY) and 4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine (10, MeOPh-TPY) ligands with the divalent metals Co2+, Fe2+, Mn2+ and Ni2+ are reported. The compounds were synthesized from a 1:2 mixture of the metal and ligand, resulting in a series of complexes with the general formula [M(R-TPY)2](ClO4)2 (where M = Co2+, Fe2+, Mn2+ and Ni2+, and R-TPY = Ph-TPY, ClPh-TPY and MeOPh-TPY). The general formula and structural and supramolecular features were determinated by single-crystal X-ray diffraction for bis(4′-phenyl-2,2′:6′,2′′-terpyridine)nickel(II) bis(perchlorate), [Ni(C21H15N3)2](ClO4)2 or [Ni(Ph-TPY)2](ClO4)2, bis[4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(perchlorate), [Mn(C22H17N3O)2](ClO4)2 or [Mn(MeOPh-TPY)2](ClO4)2, and bis(4′-phenyl-2,2′:6′,2′′-terpyridine)manganese(II) bis(perchlorate), [Mn(C21H15N3)2](ClO4)2 or [Mn(Ph-TPY)2](ClO4)2. In all three cases, the complexes present distorted octahedral coordination polyhedra and the crystal packing is determined mainly by weak C—H...π interactions. All the compounds (except for the Ni derivatives, for which FT–IR, UV–Vis and thermal analysis are reported) were fully characterized by spectroscopic (FT–IR, UV–Vis and NMR spectroscopy) and thermal (TGA–DSC, thermogravimetric analysis–differential scanning calorimetry) methods.

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Section: Uv-vis Spectrophotometrymentioning

confidence: 84%

Synthesis, characterization and structural analysis of complexes from 2,2′:6′,2′′-terpyridine derivatives with transition metals

Fajardo,

Arteaga,

Ellena

et al. 2024

Acta Crystallogr C

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“…[31] More-over, it has been suggested that the N-methyl-D-glucamine component and azo dye moiety could engage distinct receptor permeation pathways, [32][33][34][35] potentially heightening the biological potency of newly created compounds. This study represents a segment of our ongoing research program, [36][37][38][39][40] which centers on the development of new pyrazole, pyridine, and pyrimidine derivatives incorporating an azo dye moiety via a derivative of enaminonitrile. Our goal is to establish a novel foundation for producing natural, bioactive compounds that could potentially be highly effective.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

et al. 2023

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The reaction of N‐(4‐(phenyldiazenyl) phenyl) carbonohydrazonoyl dicyanide (2) with N‐methyl glucamine afforded 3‐amino‐3‐(methyl (2,3,4,5,6‐pentahydroxyhexyl)amino)‐2‐((4‐(phenyldiazenyl)phenyl)diazenyl)acrylonitrile (3). Additionally, compound 2 produced the pyrazole derivatives 4 and 6, respectively, by reactions with hydrazine hydrate and malononitrile. Moreover, when enaminonitrile 3 was treated with malononitrile, N,N‐Dimethylformamide ‐ dimethyl acetal, and thiourea, it generated the glucaminoid derivatives 9, 10, and 13, respectively. In pyridine, compound 19 was obtained when enaminonitrile 3 interacted with the carbon disulfide. While in sodium hydroxide in N,N‐Dimethylformamide, instead of pyridine, it afforded the methyl carbamodithioate 23. Finally, pyrimidinethione derivative 26 was produced when the enaminonitrile 3 and phenyl isothiocyanate interacted. All new compounds were well established by both spectral and elemental analyses. The antitumor activities were evaluated by testing their impact on the viability of four different cell lines: HepG2 (human hepatocellular liver carcinoma), WI‐38 (human lung fibroblast), VERO (African green monkey kidney epithelial), and MCF‐7 (human breast adenocarcinoma). The antitumor study showed that compound 23 has very strong antitumor activity against the HEPG‐2 cell line. The synthesized compounds were analyzed by docking studies that showed good binding scores against the diverse amino acids of the selected proteins B‐Cell Leukemia/Lymphoma‐2 (Bcl‐2). The conducted docking studies were found to be consistent with cytotoxic results.

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“…Additionally, Scontaining b-lactam ring system is present in commercially available antibiotics such as penicillin and cephalosporin. [31][32][33][34][35] The applications of heterocyclic motifs in medicinal chemistry and chemical sciences are very vast as illustrated by the marketed medicines containing N, O, and S heteroatoms. The exceptional function of these heteroatoms in a variety of interactions with essential biological targets broadens the possibility of drug design and development.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, S -containing β-lactam ring system is present in commercially available antibiotics such as penicillin and cephalosporin. 31–35…”

Section: Introductionmentioning

confidence: 99%

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

et al. 2022

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Chalcone- and flavone-based novel terpyridine metal complexes: Synthesis, electrochemical, photophysical, photovoltaic and computational studies

Cited by 11 publications

References 54 publications

Synthesis, characterization and structural analysis of complexes from 2,2′:6′,2′′-terpyridine derivatives with transition metals

Synthesis, characterization and structural analysis of complexes from 2,2′:6′,2′′-terpyridine derivatives with transition metals

Synthesis of Pyrazole, Pyridine, and Pyrimidine Derivatives Incorporating Glucaminoid Moiety and Their Antioxidant, Antitumor Activities and Docking Study

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

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