Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity

Kostecka, Małgorzata

doi:10.3390/molecules17033560

Cited by 10 publications

(4 citation statements)

References 18 publications

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“…Antifungal properties of compounds containing sulfur and nitrogen have been well documented in literature [40,41,42,43,44,45,46]. Among these substances also various thiosemicarbazones [47,48,49,50,51,52] and derivatives of 1,3-thiazolidin-4-one were reported [53,54,55,56,57,58,59,60,61,62,63].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

Opletalová

Dolezel²,

Kuneš

et al. 2016

Molecules

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Abstract:Two novel thiosemicarbazones and eight novel 2-{[1-(5-alkyl/arylalkylpyrazin-2-yl) ethylidene]hydrazono}-1,3-thiazolidin-4-ones were prepared and tested against a panel of eight fungal strains-Candida albicans ATCC 44859, Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I, Trichosporon asahii 1188, Aspergillus fumigatus 231, Lichtheimia corymbifera 272, and Trichophyton interdigitale 445. 1,3-Thiazolidin-4-ones exhibited activity against all strains, the most potent derivative was 2-{[1-(5-butylpyrazin-2-yl)ethylidene]hydrazono}e-1,3-thiazolidin-4-one. Susceptibility of C. glabrata to the studied 1,3-thiazolidin-4-ones (minimum inhibitory concentrations (MICs) were in the range 0.57 to 2.78 mg/L) is of great interest as this opportunistic pathogen is poorly susceptible to azoles and becomes resistant to echinocandins. Antifungal potency of thiosemicarbazones was slightly lower than that of 1,3-thiazolidin-4-ones.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

Opletalová

Dolezel²,

Kuneš

et al. 2016

Molecules

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“…This reaction represents nucleophilic substitution reaction and its mechanism involved nucleophilic attack of amino group in hydrazine on carbonyl group in ester followed by elimination of ethanol molecule [25], as shown in the following Scheme:…”

Section: Synthesis Of Morpholin-nacetohydrazide(2)mentioning

confidence: 99%

Synthesis and Characterization of Some New Morpholine Derivatives

Journal¹

2016

Baghdad Sci.J

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In this paper a new series of morpholine derivatives was prepared by reacting the morpholine with ethyl chloro acetate in the presence triethylamine as a catalyst in benzene gave morpholin-N-ethyl acetate(1) which reacted with hydrazine hydrate in ethanol, and gave morpholin-N-ethyl acetohydrazide (2) . Morpholin-N-aceto semithiocarbazide (3) were prepared by reacting compound(2) with ammonium thiocyanate , concentrated hydrochloric acid and ethanol as a solvent .Compound (3) reacted with sodium hydroxide and hydrochloric acid to give 5-(morpholin-N-methylene)-1H-1,2,4-triazole-3-thiol (4) .The new series of 1,2,4-triazol derivatives (5-8) was synthesized by reaction of compound(4) with formaldehyde , DMF as a solvent and different secondary amines. Preparation of new 1,2,4-triazoline derivatives (9) by reaction compound (4) with bromo acetic acid . Reaction of compound (9) with different aromatic aldehyde and dimethyl sulfoxide as a solvent obtained compounds (10-13).

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“…Hydrazides have been described as useful key compound to synthesize various heterocyclic compounds . Hydrazides are reported to have different and rich biological properties . Hydrazones are used in electrophotography, due to their relatively simple synthesis, low molecular weight, and aperture‐conveying properties .…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

Hamama

Ibrahim

Gooda

et al. 2018

Journal of Heterocyclic Chem

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A novel series of Schiff bases, hydrazide, and hydrazine derivatives containing quinoline moiety were synthesized via condensation of 3-substituted quinolines 1a and 1b with different aromatic amines or hydrazines. Furthermore, various heterocyclic ring systems: 1,3,4-thiadiazole, thiazolidin-4-one, 2-thioxoimidazolidin-4-one, and thiazole derivatives 10-13 were synthesized by refluxing hydrazinecarbothioamide derivative 9 with different acetic acid derivatives. Theoretical calculation of the title compounds were carried out using density functional theory method. The geometrical optimization of the prepared target compounds was theoretically analyzed. The synthesized compounds were examined for their antimicrobial and antioxidant activities. The obtained results revealed clearly that compounds 8 and 13 displayed promising activity as an antimicrobial activity and compounds 3, 5, 6, 7, and 9 exhibited better radical scavenging ability. Scheme 3. Transformation reaction of thiosemicarbazone derivative 9 to quinolone-attached 5-membered heterocyclic moieties 10-13. Scheme 2. Reaction of 2-substituted quinoline-3-carbaldehyde 1a and 1b with hydrazine derivatives.

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Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity

Cited by 10 publications

References 18 publications

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

Synthesis and Antifungal Screening of 2-{[1-(5-Alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones

Synthesis and Characterization of Some New Morpholine Derivatives

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

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