Synthesis and Tuberculostatic Activity of Some 1,1-Bis-methylthio-2-nitro-ethene Derivatives

Foks, Henryk; Pancechowska-Ksepko, Danuta; Janowiec, M; Zwolska, Zofia; Augustynowicz-Kopeé, Ewa

doi:10.1080/104265090920921

Cited by 16 publications

(4 citation statements)

References 10 publications

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“…The double bond on the cyclic 1,1-enediamine bears the characteristic of high polarization resulting from the conjugation effect of an electron-withdrawing substituent and a strong electron-donating amino group . The α-carbon is the first reaction site when the intermediate is attacked by the electrophilic reagents owing to the delocalization effect of the lone pair electron on the nitrogen atom. , Various adducting reactions of methyleneimidazolidine with electrophiles such as heterocyclic aldehyde, benzyl bromide, ethyl propiolate, diphenylnitrile imine, and diazonium salt proceed smoothly and have been reported previously, ,− which proved to us the possibility of synthesizing the phenylazoneonicotinoids by reaction with different substituted diazonium salts (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

Xia

Shao

et al. 2011

J. Agric. Food Chem.

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On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the π-π interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral ((1)H NMR, (13)C NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids ( Aphis craccivora ). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

Xia

Shao

et al. 2011

J. Agric. Food Chem.

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“…The compounds (EMIM) + (Ac) -, (EMIM) + (Br) -, and (BMIM) + (BF 4 ) -(Figure 1a), with purity ≥95%, acids, and cleaning materials used in the experiments were acquired from Merck Sigma-Aldrich. The HPY inhibitor was produced in the laboratory (Figure 1b), according to the modified synthesis described previously 31 , using a mixture of 1,3-diaminepropan-2-ol (5 mmol) and 1,1-bis-methylsulfanyl-2-nitromethylene (5 mmol), with ethanol (15 mL) as solvent, in a flask suitable for reactions in a microwave reactor (reaction 1). Microwave irradiation was applied for 20 min, to assist the double vinylic substitution according to an addition-elimination mechanism, producing 5-hydroxy-2-nitromethylenehexahydropyrimidine (HPY), with a yield of 82% after purification by filtration and extensive washing using cold ethanol.…”

Section: Methodsmentioning

confidence: 99%

Combining Electrochemical and Theoretical Analysis to Evaluate Hydrogen Permeation Inhibitors During Free Corrosion

Silvério,

Araujo,

Carvalho

et al. 2024

Mat. Res.

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In this work, electrochemical tests were performed to measure hydrogen permeation during free dissolution of carbon steel in the presence of the ionic liquids (ILs) 1-ethyl-3-methylimidazolium acetate [(EMIM) + (Ac) -], 1-ethyl-3-methylimidazolium bromide [(EMIM) + (Br) -], and 1-butyl-3-methylimidazolium tetrafluoroborate [(BMIM) + (BF 4 ) -] in 5.4 mol L -1 HCl aqueous solution. The permeation inhibition efficiencies (IEp (%)) of 5-hydroxy-2-nitromethylene-hexahydropyrimidine (HPY) and a commercial corrosion inhibitor (CCI) were also evaluated. Among the ILs, the (BMIM) + (BF 4 )compound presented the highest corrosion and hydrogen permeation inhibition efficiencies, with values of 23% and 30%, respectively. The (EMIM) + (Br)and (EMIM) + (Ac)compounds were not effective against corrosion, but they presented IEp of 15.8% and 23%, respectively. The HPY compound demonstrated 61% effectiveness in preventing corrosion, while in silico evaluation indicated no toxicity. However, neither the HPY compound nor the CCI compound inhibited the entry of hydrogen into the carbon steel during the pickling process.

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“…2‐(nitromethylene)hexahydropyrimidin‐5‐ol ( 11 ) (Foks et al., 2005): Yield 90%. Melting point: 221°C–224°C (decomposition).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and cytotoxic evaluation of heterocyclic compounds by vinylic substitution of ketene dithioacetals

Baliza,

Freitas,

Gonçalves

et al. 2024

Chem Biol Drug Des

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N‐heterocyclic compounds are important molecular scaffolds in the search for new drugs, since most drugs contain heterocyclic moieties in their molecular structure, and some of these classes of heterocycles are able to provide ligands for two or more biological targets. Ketene dithioacetals are important building blocks in organic synthesis and are widely used in the synthesis of N‐heterocyclic compounds. In this work, we used double vinylic substitution reactions on ketene dithioacetals to synthesize a small library of heterocyclic derivatives and evaluated their cytotoxic activity in breast and ovarian cancer cells, identifying two benzoxazoles with good potency and selectivity. In silico predictions indicate that the two most active derivatives exhibit physicochemical properties within the range of drug‐like compounds and showed potential to interact with HDAC8 and ERK1 cancer‐related targets.

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Synthesis and Tuberculostatic Activity of Some 1,1-Bis-methylthio-2-nitro-ethene Derivatives

Cited by 16 publications

References 10 publications

Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

Combining Electrochemical and Theoretical Analysis to Evaluate Hydrogen Permeation Inhibitors During Free Corrosion

Synthesis and cytotoxic evaluation of heterocyclic compounds by vinylic substitution of ketene dithioacetals

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