Problems with molecular mechanics implementations on the example of 4-benzoyl-1-(4-methyl-imidazol-5-yl)-carbonylthiosemicarbazide

Siwek, Agata; Świderek, Katarzyna; Jankowski, Stefan

doi:10.1007/s00894-011-1117-1

Cited by 10 publications

(7 citation statements)

References 87 publications

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“…Based on the results presented by Liesen et al [21] we expected that the replacement of the imidazole core in 4-aryl-1-(4-methyl-1H-imidazole-5-yl)carbonylthiosemicarbazide with a similarly sized five-membered heteroaryl ring would result in compounds with a comparable bioactivity profile. The designed thiosemicarbazides presented structures similar to those proposed by Liesen et al [21], with sulphur and oxygen atoms at C(=O)NHNHC(=S) core on the same side (Figure 2, left) or on the opposite side of the molecule (Figure 2, right), as confirmed by Amber calculations [22].…”

Section: Resultssupporting

confidence: 77%

1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation

et al. 2014

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A series of 4-arylthiosemicarbazides substituted at the N1 position with a 5-membered heteroaryl ring was synthesized and evaluated in vitro for T. gondii inhibition proliferation and host cell cytotoxicity. At non-toxic concentrations for the host cells all studied compounds displayed excellent anti-parasitic effects when compared to sulfadiazine, indicating a high selectivity of their anti-T. gondii activity. The differences in bioactivity investigated by DFT calculations suggest that the inhibitory activity of 4-arylthiosemicarbazides towards T. gondii proliferation is connected with the electronic structure of the molecule. Further, these compounds were tested as potential antibacterial agents. No growth-inhibiting effect on any of the test microorganisms was observed for all the compounds, even at high concentrations.

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Section: Resultssupporting

confidence: 77%

1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation

et al. 2014

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“…However, a completely different correlation in the case of other cyclohexyl ( 31 , 44 ) and phenyl ( 21 , 35 ) derivatives inspired us to conduct conformational analyses of compounds 15 , 31, and 44 . Molecule geometry optimization was performed using Amber force field which yields good results for geometries and the energetics of thiosemicarbazide derivatives . The most stable structures obtained were optimized to the closest local minimum using AM1 parametrization (implemented in HyperChem).…”

Section: Resultsmentioning

confidence: 99%

Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

et al. 2014

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Forty-five derivatives of thiosemicarbazide were synthesized, and their antibacterial activity against Gram-positive and Gram-negative bacteria was evaluated. Some of the described compounds exhibited interesting activity against reference strains of Gram-positive bacteria, whereas only two derivatives had the ability to inhibit the growth of Gram-negative species (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, Proteus mirabilis ATCC 12453). The most potent antimicrobial activity was observed in the cases of salicylic acid hydrazide derivatives. The differences in activity inspired us to conduct conformational analysis using molecular mechanics level. The obtained results suggest that the molecule geometry, especially at the N4-terminus of thiosemicarbazide skeleton, determines the antibacterial activity. Unfortunately, in opposition to what we expected, only one of the tested compounds inhibited the activity of the topoIV enzyme, and none of them was active against DNA gyrase.

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“…Conformational search, physicochemical parameters, and HOMO/LUMO maps were calculated using HyperChem 8.0.1 [ 28 ]. Extensive conformational searches were carried out using the molecular mechanics level with OPLS force field [ 29 ]. The most stable structures obtained were subsequently optimized to the closest local minimum at the semiempirical level using RM1 parametrization.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids

et al. 2018

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Series of new thiazolidine-2,4-dione-based chlorophenylthiosemicarbazone hybrids (17–40) were synthesized by the reaction of condensation chlorophenylthiosemicarbazides with formylphenyl 2-(2,4-dioxothiazolidin-5-yl/ylidene)acetates. New compounds were tested on reference strains of Gram-positive and Gram-negative bacteria. The antibacterial activity of target compounds was determined by broth dilution method. Most active compounds possess minimum inhibitory concentration (MIC) = 3.91 mg/L. These compounds were non-toxic at concentrations close to their antibacterial effect. The antibacterial activity of some compounds was similar to or higher than the activity of used reference drugs such as oxacillin and cefuroxime. The structure–activity relationships (SARs) analysis collectively suggests that at least two different molecular mechanisms of their antibacterial activity should be expected.

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Problems with molecular mechanics implementations on the example of 4-benzoyl-1-(4-methyl-imidazol-5-yl)-carbonylthiosemicarbazide

Cited by 10 publications

References 87 publications

1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation

1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation

Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids

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