Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds

Topal, Tufan

doi:10.17344/acsi.2020.6183

Cited by 11 publications

(4 citation statements)

References 67 publications

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“…30 The bond length of C(15)-O(3) was 1.3162 (15), which was shorter than the typical C-O length (1.42 Å); the bond length of C( 10)=C(15) (1.3841(16) Å) and C(9)-O(1) (1.2490(15) Å) was also longer than the typical C=C length (1.34 Å) and C=O length (1.21 Å). [31][32][33] These results suggest a conjugative effect between carbonyl, hydroxyl, and C=C bond. In addition, the C(6)-C(9) bond length (1.4892(16) Å) was shorter than the typical C-C length, which could be due to a π-π conjugation between carbonyl and benzene of quinoxaline.…”

Section: Description Of the Crystal Structures And Hydrogen Bondingmentioning

confidence: 71%

Synthesis, Crystal Structure and Biological Activity of Two Triketone-Containing Quinoxalines as HPPD Inhibitors

Leng

Liu²,

Ye³

2022

ACSi

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Two new triketone-containing quinoxaline derivatives were designed by fragment splicing strategy and synthesized using 3,4-diaminobenzoic acid and substituted cyclohexanedione as starting materials. Both compounds were characterized by IR, 1H and 13C NMR, HRMS and X-ray diffraction. 3-Hydroxy-5-methyl-2-(quinoxaline-6-carbonyl)cyclohex-2-en-1-one (6a) crystallized in the triclinic system, space group Pī, a = 7.9829(2) Å, b = 8.1462(2) Å, c = 10.7057(3) Å, α = 84.3590(10)°, β = 89.7760(10)°, γ = 87.4190(10)°, Z = 2, V = 692.12(3) Å3, F(000) = 296, Dc = 1.335 Mg/m3, μ(MoKα) = 0.095 mm–1, R = 0.0683 and wR = 0.1983. 3-Hydroxy-5,5-dimethyl-2-(3-ethoxyquinoxaline-6-carbonyl)cyclohex-2-en-1-one (6b) crystallized in the monoclinic system, space group P21/c, a = 10.1554(6) Å, b = 9.6491(6) Å, c = 17.7645(10) Å, β = 90.784(2)°, Z = 4, V = 1740.59(18) Å3, F(000) = 720, Dc = 1.299 Mg/m3, μ(MoKα) = 0.092 mm–1, R = 0.0462 and wR = 0.1235. Physicochemical property comparison and ADMET prediction showed that compound 6a had similar properties to the commercial herbicide mesotrione. Molecular docking results showed that the interactions between 6a and AtHPPD were similar to mesotrione. Moreover, the extended aromatic ring system and the additional alkyl form more interactions with the surrounding residues. Examination of AtHPPD inhibition and herbicidal activity showed that 6a had similar inhibition values to mesotrione and had a superior inhibitory effect on Echinochloa crus-galli.

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Section: Description Of the Crystal Structures And Hydrogen Bondingmentioning

confidence: 71%

Synthesis, Crystal Structure and Biological Activity of Two Triketone-Containing Quinoxalines as HPPD Inhibitors

Leng

Liu²,

Ye³

2022

ACSi

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“…The downward shift of the phenolic OH proton absorption can be attributed to the presence of strong intramolecular hydrogen bonding in these compounds. [22][23][24] The other proton resonances of these ligands are given experimental section.…”

Section: Characterization Of the Compoundsmentioning

confidence: 99%

Synthesis, Crystal Structure and In Vitro Cytotoxicity of Novel Cu(II) Complexes Derived from Isatin Hydrazide-Hydrazone Ligands

Topkaya

2023

ACSi

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In this study, two innovative hydrazine-hydrazone ligands were synthesized through the chemical reaction involving the isatin moiety with 4-hydroxybenzohydrazide and salicyloylhydrazine. Subsequent to the synthesis of these ligands, Cu(II) complexes were meticulously prepared, and their molecular structures were comprehensively analyzed utilizing an array of spectroscopic techniques. Furthermore, the crystallographic investigation was employed to elucidate the precise crystal structure of the Cu(L2)2 complex, incorporating the salicyloylhydrazine moiety. The research focuses on investigating the cytotoxic effects of Cu(II) complexes bearing isatine groups on cancer cells. These complexes were tested against lung carcinoma (A549) and breast carcinoma (MCF-7) cell lines using the MTT assay, with cisplatin as a positive control. Additionally, their effects on human normal cell line 3T3 were assessed. The Cu(L1)2 complex exhibited significant inhibitory effects on tumor cells in a dose-dependent manner, although not as potent as cisplatin. The cytotoxic selectivity indices (SI) indicated acceptable selectivity levels for both cancer cell lines, indicating potential for selective lethality. The crystal structure of one compound was confirmed, revealing van der Waals interactions and hydrogen bonding in the packing.

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“…The contacts for which the distance between the interacting atoms is equal to the sum of the van der The intermolecular interactions can be further explored with the utilization of two-dimensional fingerprint plots which is a key analysis to separately identify and quantify the interatomic contacts. [37][38][39][40] Figure 6a is the 2D fingerprint plot for overall interactions on which short interactions contacts are shown by large spikes. In most crystal structures of organic compounds, H•••H contacts are the most significant contributors in the crystal packing but in our case, the O•••H contacts are the most significant contributors in the crystal packing with a percentage contribution of 39.8% (Figure 6b).…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Synthesis, SC XRD Based Structure Elucidation, Supramolecular Assembly Exploration Via Hirshfeld Surface Analysis, Computational and QTAIM Study of Functionalized Anilide

Tahir,

Ashfaq,

Ali

et al. 2023

ACSi

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The anilide compound named (Z)-4-(2-methoxy-4-nitrophenyl)amino)-4-oxobut-2-enoic acid (MAOA) has been synthesized by the chemical reaction of 2-methoxy-4-nitroaniline and maleic anhydride in ethyl acetate. The synthesized compound was characterized by elemental analysis, FT-IR and UV-Vis spectroscopy, and TGA/DSC technique. Furthermore, the crystal structure was analyzed by the single crystal X-ray diffraction (SC XRD) technique. The supramolecular assembly of MAOA in terms of non-covalent interactions was explored by Hirshfeld surface analysis. Void analysis inferred that MAOA is expected to have good mechanical properties. The crystal packing environment was further investigated by interaction energy between molecular pairs and energy frameworks. Moreover, the result of the gas-phase DFT study showed that there is an intramolecular N–H···O and O–H···O hydrogen bond in MAOA due to the distance between D and A being smaller than the sum of their van der Waals radii. The result of the QTAIM study showed that there should also be an intramolecular CH···O hydrogen bond with a strength of 3.40 kcal/mol in MAOA.

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Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds

Cited by 11 publications

References 67 publications

Synthesis, Crystal Structure and Biological Activity of Two Triketone-Containing Quinoxalines as HPPD Inhibitors

Synthesis, Crystal Structure and Biological Activity of Two Triketone-Containing Quinoxalines as HPPD Inhibitors

Synthesis, Crystal Structure and In Vitro Cytotoxicity of Novel Cu(II) Complexes Derived from Isatin Hydrazide-Hydrazone Ligands

Synthesis, SC XRD Based Structure Elucidation, Supramolecular Assembly Exploration Via Hirshfeld Surface Analysis, Computational and QTAIM Study of Functionalized Anilide

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