Synthesis and antimicrobial activity of tetradentate ligands bearing hydrazone and/or thiosemicarbazone motifs and their diorganotin(IV) complexes

González-García, Cristina; Mata, Alejandro; Zani, Franca; Mendiola, M. Antonia; López‐Torres, Elena

doi:10.1016/j.jinorgbio.2016.07.002

Cited by 28 publications

(19 citation statements)

References 38 publications

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“…The crystals of [ 1 EtOH] EtOH were very small and could not be measured in a standard equipment, but they could be measured in a Supernova diffractometer. Due to is tiny size the final R value is high (0.1356) and the structure presents other refinement problems, but the crystal structure is strongly supported by all the spectroscopic and spectrometric techniques used, as well as by the crystal structures previously reported for analogous complexes bearing NH i Pr or NHCy instead of NH 2 …”

Section: Resultsmentioning

confidence: 70%

“…When complex 1 is recrystallized in ethanol two solvent molecules are incorporated, one coordinated to the metal and the other as a crystallization molecule to give [ 1 EtOH]EtOH . Coordination of a donor solvent such as H 2 O, EtOH, DMF or DMSO was previously observed in related complexes . The ligand is doubly deprotonated and binds to the tin as a N 2 SO tetradentate chelate, giving rise to the formation of three five‐member chelate rings that confers great stability to the complex.…”

Section: Resultsmentioning

confidence: 86%

“…Two equivalents of lithium hydroxide were added to induce ligand deprotonation. It is worth to note that, similarly to the ligand with cyclohexyl and in contrast with the isopropyl derivative, symmetrisation of the ligand to give the bis (hydrazone) complexes does not occur.…”

Section: Resultsmentioning

confidence: 99%

“…Hydrazones and thiosemicarbazones have received much attention over the last decades due to their fascinating structural versatility together with their outstanding therapeutic activities, such as antitumor, antiviral, antiprotozoal, antibacterial or antifungal agents . As a continuation of our studies on the synthesis and antimicrobial activity of organotin (IV) complexes with thiosemicarbazone/hydrazone ligands, we have synthesized two ligands, one mixed thiosemicarbazone/hydrazone ligand, L 1 H 2 , and one mono (thiosemicarbazone), HATs, and their complexes with SnR 2 Cl 2 and SnR 3 Cl (R = Me, Bu, Ph), respectively. In a previous work we have found that introduction of a lipophilic pendant group in the terminal amine of the thiosemicarbazone do not increase the antimicrobial activity of the complexes, so we decided to introduce a NH 2 group, which is less lipophilic but has less steric hindrance to evaluate if the ligand size could have any influence in the antimicrobial properties.…”

Section: Introductionmentioning

confidence: 99%

“…As a continuation of our studies on the synthesis and antimicrobial activity of organotin (IV) complexes with thiosemicarbazone/hydrazone ligands, we have synthesized two ligands, one mixed thiosemicarbazone/hydrazone ligand, L 1 H 2 , and one mono (thiosemicarbazone), HATs, and their complexes with SnR 2 Cl 2 and SnR 3 Cl (R = Me, Bu, Ph), respectively. In a previous work we have found that introduction of a lipophilic pendant group in the terminal amine of the thiosemicarbazone do not increase the antimicrobial activity of the complexes, so we decided to introduce a NH 2 group, which is less lipophilic but has less steric hindrance to evaluate if the ligand size could have any influence in the antimicrobial properties. We also used tri‐ and diorganotin (IV) precursors to modify the overall lipophilicity of the derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Huedo

Zani

Mendiola

et al. 2018

Applied Organom Chemis

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Six organotin (IV) complexes with two ligands derived from 2,3‐butanedione and thiosemicarbazide have been synthesized and fully characterized by several spectroscopic techniques, including 119Sn NMR and single crystal X‐ray diffraction. Reactions of the ligand diacetyl‐2‐(thiosemicarbazone)‐3‐(3‐hydroxy‐2‐naphthohydrazone), L1H2, with SnR2Cl2 (R = Me, Bu, Ph) lead to the obtaining of complexes 1–3 with general formula [SnR2L1] (R = Me 1, R = Bu 2, R = Ph 3), in which the ligand is doubly deprotonated and behaves as a N2SO donor, whereas from the reactions of diacetyl‐2‐thiosemicarbazone, HATs, with the same organotin precursors any complex could be isolated. By contrast, reaction of HATs with SnR3Cl induces the ligand cyclization to form a 1,2,4‐triazine‐3‐thione that binds to the metal as a monoanionic donor in a mono or bidentate manner to form compounds 4–6 with formula [SnR3L2] (R = Me 4, R = Bu 5, R = Ph 6). The antimicrobial activity of the ligands and the six complexes was tested towards bacteria and fungi, including clinical isolated strains. The results show that the ligands are devoid of activity, except HATs that displays activity against Bacillus subtilis. Conversely, the complexes exhibit good antimicrobial properties against Gram positive and negative bacteria, yeasts and moulds. The best results are obtained for complexes [SnBu3L2] 5 and [SnPh3L2] 6, indicating that their more lipophilic nature could play an important role in the ease of microbial cell penetration. In some cases, these complexes display similar or higher activity than that of ampicillin and miconazole, used as antibacterial and antifungal positive controls, respectively. Docking study with DHPS protein (S. aureus) has shown that out of six drugs, the compound 6 has the best binding affinity (−8.5 Kcal/mol).

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Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Huedo

Zani

Mendiola

et al. 2018

Applied Organom Chemis

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Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Taxak,

Devi,

Dubey

et al. 2023

Applied Organom Chemis

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In the search of novel and effective anti‐infectious agents, new hydrazone ligands (1–4) and their diorganotin (IV) complexes (5–20) were synthesized by condensing piperonylic hydrazide with salicylaldehyde derivatives, which have been further characterized by numerous physical and spectral techniques [1H, 13C, 119Sn] NMR, mass spectroscopy, UV–Vis, IR). These techniques ascertained dibasic tridentate coupling of hydrazone ligands with diorganotin (IV) through phenolic, enolic oxygens, and imine nitrogen, demonstrating pentacoordinated stereochemistry of the complexes. The thermal stability of up to 160°C of the complexes was ascertained by TGA studies whereas low conductance signified compounds have non‐electrolytic nature. Further, the antimicrobial activity was evaluated against four bacterial and two fungal strains by serial dilution assay, which demonstrated that the metal complexes (10, 11, 12) have comparable MIC values (0.0085–0.0098 μmol/ml) with ciprofloxacin and excellent biological responses in comparison of fluconazole. The phenyl complex [Ph2SnL2] (12) was found to be the most active antimicrobial agent with the lowest MIC value (0.0085 μmol/ml). The compounds were also screened for in vitro anti‐inflammatory activity by BSA denaturation assay and the phenyl complex [Ph2SnL2] (12) has been reported as most potent with 7.62 IC50 value, which is comparable with diclofenac sodium. Further, the biologically active complexes (9–12) and their hydrazone ligand [H2L2] were theoretically analyzed by computational investigations to support the in vitro results. The molecular docking analysis of compounds was performed on the active site of C. albicans (PDB ID: 5V5Z) and E. coli (PDB ID: 1HNJ) to assess the binding interactions and binding energy. The DFT and MESP (2, 9–12) revealed the most reactive areas, molecular geometry, Mulliken atomic charges, electronegativity, etc. of the compounds (2, 9–12). The ADMET profile showed the toxicity level and drug‐likeness properties, showing their potential to operate as viable antagonists.

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Antibacterial Screening of Nitrogen and Sulphur Donor Atom Containing Methylcarbamatethiosemicarbazone and Its Mn(II) and Co(II) Complexes: Synthesis, Spectroscopic Approach, Molecular Modeling

Goel

Kumar

Chandra³

2018

Iran J Sci Technol Trans Sci

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Synthesis and antimicrobial activity of tetradentate ligands bearing hydrazone and/or thiosemicarbazone motifs and their diorganotin(IV) complexes

Cited by 28 publications

References 38 publications

Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Investigation of anti‐inflammatory and antimicrobial activities of hydrazone‐based diorganotin (IV) complexes: Synthesis, spectroscopic characterization, and computational studies

Antibacterial Screening of Nitrogen and Sulphur Donor Atom Containing Methylcarbamatethiosemicarbazone and Its Mn(II) and Co(II) Complexes: Synthesis, Spectroscopic Approach, Molecular Modeling

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