Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Gholivand, Khodayar; EbrahimiValmoozi, Ali Asghar; Gholami, Akram; Dušek, Michal; Eigner, Václav; Abolghasemi, Sara

doi:10.1016/j.jorganchem.2015.09.030

Cited by 27 publications

(18 citation statements)

References 32 publications

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“…Gholivand et al have reported the antimicrobial activity of tin(IV) complexes with phosphonic diamide derivatives, as the used concentrations 5 and 10 mg/ml against S. aureus , P.aeruginosa, B. cereus , B. subtillus, E. coli , and P. stutzori . They have also investigated the antimicrobial activity of tin(IV) complexes of diphosphoryl derivatives, showing considerable activity against B. cereus and E. coli (MIC 0.78–12 and 2.5–10 μg/ml) . High activity for {[R 2 SnL 2 ] (R = Me, Et, Bu, Oct) and [R 3 SnL] n (R = Bu, Ph) (L = O 2 CCH 2 C 6 H 4 OCH 3 –4)} have been reported against S. aureus , B. subtillus, and S.typhi with concentration 1 mg/ml .…”

Section: Resultsmentioning

confidence: 99%

“…The coordination chemistry of organotin compounds has become of great interest because of their important applications as anticancer agents, agrochemical fungicides and biocides, as well as catalysts . Synthesis of organotin with phosphoramide ligands by the reaction of Sn(R) n Cl 4‐n ( n = 1–3) (R = Cl, CH 3 , C 6 H 5 ) with various phosphoramides, as well as evaluation of their cytotoxicity against some human cell lines and microbial strains have frequently been studied . Recently, the development of coordination complexes as nano‐structured materials has increased for nanotechnological applications because of their superior physical and chemical properties that cannot be observed in bulk counterparts.…”

Section: Introductionmentioning

confidence: 99%

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Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Dorosti

Delfan

Khodadadi

2017

Applied Organom Chemis

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{L = C 6 H 5 (O)P(NHC 6 H 11 ) 2 } have been synthesized by sonochemical processes at different concentrations without any surfactant or capping agent. The structure and morphology of the prepared complex were investigated by using SEM-EDAX, XRD, DLS, UV-Vis and FT-IR spectroscopy. Nanoparticles with well-defined rod shapes and sizes in the range 30-40 nm have been obtained. Also bulk form of the titled complex was synthesized and characterized by 1 H, 13 C, 31 P, 119 Sn NMR, UV-Vis and FT-IR spectroscopy and compared with its nano-size. The thermal stabilities at bulk and nano-size scale have been studied by thermal gravimetric (TG) and differential thermal analysis (DTA). Further, SnP 2 O 7 nanoparticles were synthesized by direct calcination at 730°C under air atmosphere and characterized using XRD, SEM, and TEM. From XRD measurements, we determined the mean size of the crystallites about 27.4 nm. It is found that the size and morphology of the tin pyrophosphate nano-structures are dependent upon the particles size of precursor compound as well. Two different forms of metal coordination compound (1a, 1b) and the corresponding ligand (L) were screened for their antibacterial activity against the selected Gram-positive and Gramnegative bacteria, showing bactericidal activity for complexes 1a and 1b. In vitro cytotoxicity of compounds was studied against human carcinoma cell lines, A2780 (ovarian cancer) and PC-3 (prostate cancer). Results indicated that 1a and 1b possess relatively strong cytotoxic activity against cancer cells with IC 50 values ranging from 93.2 to 376.2 μM for two exposure time (24 and 48 h).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Dorosti

Delfan

Khodadadi

2017

Applied Organom Chemis

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“…Ligand selectivity can be introduced into a system in order to determine their effectiveness in bioactivity, particularly in anticancer activity. Ligands not only modify the solubility in lipid permeable membranes, but also play a role in transporting and addressing the compound to their specific target site [21]. On this note, Schiff bases have long been studied as potential target ligands to enhance the bioactivity of chemotherapeutic drugs.…”

Section: Introductionmentioning

confidence: 99%

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

Yusof

Latif

Tahir

et al. 2020

Journal of Molecular Structure

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Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H 2 L1, H 2 L2 and H 2 L3) and 2,3-dihydroxybenzaldehyde (H 2 L4, H 2 L5 and H 2 L6) (where H 2 Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1 H, 13 C and 119 Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3 to be quite similar in which the dinegative tridentate ligand coordinated the tin atoms via thiolate-S, phenoxide-O and imine-N atoms. The coordination geometries are based on an octahedron with like-atoms mutually trans. The *Revised Manuscript Click here to view linked References 2 experimental findings were validated by density functional theory (DFT) calculations at the B3LYP/LanL2DZ/6-311G(d,p) level of theory. All the tin(IV) compounds, except the insoluble compound 2 were screened for their in vitro cytotoxicity against a panel ten of cancer cell lines and one normal breast cell line (MCF-10A) by MTT assay. Interestingly, the cytotoxicity of five tin(IV) compounds against HT29, MCF7 and MIA was higher than the reference drug, cisplatin.

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“…Many kinds of amino have free amino groups that provide the possibility to generate cinnamaldehyde-amino Schiff base. In a previous paper, Reference [ 16 ], cinnamaldehyde-amino acids compounds were synthesized with several kinds of amino acid and cinnamaldehyde derivatives, and the resulting compounds showed comparable antibacterial activity to ciprofloxacin against S. aureus and E. coli. Furthermore, cinnamaldehyde-amino acid Schiff base compounds significantly decreased the drawbacks of cinnamaldehyde (e.g., high volatility, insolubility in water, and foul odor).…”

Section: Introductionmentioning

confidence: 99%

Screening, Synthesis, and QSAR Research on Cinnamaldehyde-Amino Acid Schiff Base Compounds as Antibacterial Agents

et al. 2018

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Development of new drugs is one of the solutions to fight against the existing antimicrobial resistance threat. Cinnamaldehyde-amino acid Schiff base compounds, are newly discovered compounds that exhibit good antibacterial activity against gram-positive and gram-negative bacteria. Quantitative structure–activity relationship (QSAR) methodology was applied to explore the correlation between antibacterial activity and compound structures. The two best QSAR models showed R2 = 0.9354, F = 57.96, and s2 = 0.0020 against Escherichia coli, and R2 = 0.8946, F = 33.94, and s2 = 0.0043 against Staphylococcus aureus. The model analysis showed that the antibacterial activity of cinnamaldehyde compounds was significantly affected by the polarity parameter/square distance and the minimum atomic state energy for an H atom. According to the best QSAR model, the screening, synthesis, and antibacterial activity of three cinnamaldehyde-amino acid Schiff compounds were reported. The experiment value of antibacterial activity demonstrated that the new compounds possessed excellent antibacterial activity that was comparable to that of ciprofloxacin.

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Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Cited by 27 publications

References 32 publications

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

Screening, Synthesis, and QSAR Research on Cinnamaldehyde-Amino Acid Schiff Base Compounds as Antibacterial Agents

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Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Cited by 27 publications

References 32 publications

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP2O7 nano‐structure

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP2O7 nano‐structure

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

Screening, Synthesis, and QSAR Research on Cinnamaldehyde-Amino Acid Schiff Base Compounds as Antibacterial Agents

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Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure