Synthesis, characterization, crystal structure and HSA binding of two new N,O,O-donor Schiff-base ligands derived from dihydroxybenzaldehyde and tert-butylamine

Khosravi, Iman; Hosseini, Farnaz; Khorshidifard, Mahsa; Sahihi, Mehdi; Rudbari, Hadi Amiri

doi:10.1016/j.molstruc.2016.04.094

Cited by 38 publications

(16 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There exists a non-classical hydrogen bond in a phenyl-imine form with C-H⋯N. All intramolecular bond parameters are comparable with closely related compounds in the literature [46][47][48][49][50].…”

Section: X-ray Crystal Structuresupporting

confidence: 73%

Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde

et al. 2021

View full text Add to dashboard Cite

Three Schiff bases 1-(4-chlorophenyl)-N-(naphthalen-1-yl)methanimine (1), 1-(4-methoxy phenyl)-N-(naphthalen-1-yl)methanimine (2), and 1-(4-chlorophenyl)-N-(2,6-diisopropyl phenyl)methanimine (3) were synthesized and characterized by elemental analysis, 1H and 13C NMR, FT-IR and UV-Visible spectroscopic techniques. The crystal structure of compound 3 was obtained and it revealed that the compound crystallized in a monoclinic space group P21/n and there exists an intermolecular hydrogen bond in a phenyl-imine form with C-H⋯N. Crystal data for C19H22ClN: a = 7.28280(10) Å, b = 9.94270(10) Å, c = 24.0413(2) Å, β = 97.0120(10)°, V = 1727.83(3) Å3, Z = 4, μ(Mo Kα) = 0.215 mm-1, Dcalc = 1.1526 g/cm3, 14038 reflections measured (12.42° ≤ 2Θ ≤ 52.74°), 3448 unique (Rint = 0.0223, Rsigma = 0.0182) which were used in all calculations. The final R1 was 0.0337 (I≥2u(I)) and wR2 was 0.0927 (all data). The free radical scavenging activities of all three compounds were assayed using DPPH, FRAP, and OH assays. According to results obtained, compound 2 shows effective DPPH- (IC50 = 22.69±0.14 μg/mL), FRAP+ (IC50 = 28.44±0.12 μg/mL), and OH- (IC50 = 27.97±0.16 μg/mL) scavenging activities compared with compounds 1 and 3 but less than standard antioxidant compound Trolox (TRO). Additionally, theoretical calculations for the three complexes were performed by using density functional theory (DFT) calculations at the B3LYP/6-31++G(2d,2p) level in the ground state to obtain an optimized geometrical structure and to perform an electronic, molecular electronic potential surface and natural bond orbital (NBO) analysis. The geometrical calculation obtained was found to be consistent with the experimental geometry. Further analysis was conducted using the in silico technique to predict the drug likeness, molecular and ADME properties of these molecules.

show abstract

Section: X-ray Crystal Structuresupporting

confidence: 73%

Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde

et al. 2021

View full text Add to dashboard Cite

show abstract

“…In quantum chemical analysis, Mulliken atomic charge investigation of any molecular system has a vital role to play in obtaining the dipole moment, electronic properties, and molecular polarizability of the chemical system . The Mulliken population examination of L 1 was found to use the B3LYP level with a 6‐311+G(d,p) basis set.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, and biological screening of metal complexes of novel sulfonamide derivatives: Experimental and theoretical analysis of sulfonamide crystal

Sumrra

Hassan

Imran

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

This study reports the synthesis of sulfonamide‐derived Schiff bases as ligands L1 and L2 as well as their transition metal complexes [VO(IV), Fe(II), Co(II), Ni(II), Cu(II), and Zn(II)]. The Schiff bases (4‐{E‐[(2‐hydroxy‐3‐methoxyphenyl)methylidene]amino}benzene‐1‐sulfonamide (L1) and 4‐{[(2‐hydroxy‐3‐methoxyphenyl)methylidene]amino}‐N‐(5‐methyl‐1,2‐oxazol‐3‐yl)benzene‐1‐sulfonamide (L2) were synthesized by the condensation reaction of 4‐aminobenzene‐1‐sulfonamide and 4‐amino‐N‐(3‐methyl‐2,3‐dihydro‐1,2‐oxazol‐5‐yl)benzene‐1‐sulfonamide with 2‐hydroxy‐3‐methoxybenzaldehyde in an equimolar ratio. Sulfonamide core ligands behaved as bidentate ligands and coordinated with transition metals via nitrogen of azomethine and the oxygen of the hydroxyl group. Ligand L1 was recovered in its crystalline form and was analyzed by single‐crystal X‐ray diffraction technique which held monoclinic crystal system with space group (P21/c). The structures of the ligands L1and L2 and their transition metal complexes were established by their physical (melting point, color, yields, solubility, magnetic susceptibility, and conductance measurements), spectral (UV–visible [UV–Vis], Fourier transform infrared spectroscopy, 1H NMR, 13C NMR, and mass analysis), and analytical (CHN analysis) techniques. Furthermore, computational analysis (vibrational bands, frontier molecular orbitals (FMOs), and natural bonding orbitals [NBOs]) were performed for ligands through density functional theory utilizing B3LYP/6‐311+G(d,p) level and UV–Vis analysis was carried out by time‐dependent density functional theory. Theoretical spectroscopic data were in line with the experimental spectroscopic data. NBO analysis confirmed the extraordinary stability of the ligands in their conjugative interactions. Global reactivity parameters computed from the FMO energies indicated the ligands were bioactive by nature. These procedures ensured the charge transfer phenomenon for the ligands and reasonable relevance was established with experimental results. The synthesized compounds were screened for antimicrobial activities against bacterial (Streptococcus aureus, Bacillus subtilis, Eshcheria coli, and Klebsiella pneomoniae) species and fungal (Aspergillus niger and Aspergillus flavous) strains. A further assay was designed for screening of their antioxidant activities (2,2‐diphenyl‐1‐picrylhydrazine radical scavenging activity, total phenolic contents, and total iron reducing power) and enzyme inhibition properties (amylase, protease, acetylcholinesterase, and butyrylcholinesterase). The substantial results of these activities proved the ligands and their transition metal complexes to be bioactive in their nature.

show abstract

“…MD simulation [ 35 – 37 ] method was used to compare the structural changes of proteins in the absence and presence of 3HF and 7HF. The flavonol-protein complexes with the most negative free binding energy were considered as the initial conformations for the MD studies.…”

Section: Methodsmentioning

confidence: 99%

Differential roles of 3-Hydroxyflavone and 7-Hydroxyflavone against nicotine-induced oxidative stress in rat renal proximal tubule cells

et al. 2017

Self Cite

View full text Add to dashboard Cite

Plant flavonoids are well known as antioxidants against oxidative stress induced by exposure to external pollutants. Nicotine (NIC) is one of those agents which increases renal oxidative stress, an important factor in the pathogenesis of renal epithelial injury in smokers. Although several studies had been conducted on flavonoids and oxidative stress, the mechanism of the protective pathways are not fully understood. Here, we present studies on antioxidant properties of two mono-hydroxyflavone isomers, 3-hydroxyflanove (3HF)- and 7-hydroxyflavone (7HF), against nicotine-associated oxidative stress and injury in cultured renal proximal tubule cells and correlate their antioxidant properties with their chemical structure. Our data clearly demonstrates, for the first time, that while both 3HF and 7HF protect renal cells from NIC-associated cytotoxicity, the mechanism of their action is different: 3HF elicits protective activity via the PKA/CREB/MnSOD pathway while 7HF does so via the ERK/Nrf2/HO-1 pathway. Molecular docking and dynamics simulations with two major signaling pathway proteins showed significant differences in the binding energies of 3HF (-5.67 and -7.39 kcal.mol-1) compared to 7HF (-5.41 and -8.55 kcal.mol-1) in the matrices of CREB and Keap1-Nrf2 proteins respectively, which corroborate with the observed differences in their protective properties in the renal cells. The implications of this novel explorative study is likely to promote the understanding of the mechanisms of the antioxidative functions of different flavones.

show abstract

Synthesis, characterization, crystal structure and HSA binding of two new N,O,O-donor Schiff-base ligands derived from dihydroxybenzaldehyde and tert-butylamine

Cited by 38 publications

References 69 publications

Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde

Synthesis, crystal structure with free radical scavenging activity and theoretical studies of Schiff bases derived from 1-naphthylamine, 2,6-diisopropylaniline, and substituted benzaldehyde

Synthesis, characterization, and biological screening of metal complexes of novel sulfonamide derivatives: Experimental and theoretical analysis of sulfonamide crystal

Differential roles of 3-Hydroxyflavone and 7-Hydroxyflavone against nicotine-induced oxidative stress in rat renal proximal tubule cells

Contact Info

Product

Resources

About