Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds

Газиева, Галина А.; Кравченко, Ангелина Н.

doi:10.1070/rc2012v081n06abeh004235

Cited by 46 publications

(15 citation statements)

References 52 publications

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“…In this section, we used thiosemicarbazone as a precursor for the synthesis of a variety of bioactive sulfur-nitrogen heterocyclic systems as known [10,11] . Therefore, Compound 10 was treatment with concentrated hydrochloric acid to cyclization carbothioamide into 5-(1Hindol-3-yl)-5-methyl-4,5-dihydro-1,3,4-thiadiazol-2-amine 11.…”

Section: Methodsmentioning

confidence: 99%

Construction, Molecular Docking, Antimicrobial and Antioxidant Activity of Some Novel 3-Substitued Indole Derivatives Using 3-Acetyl Indole

Ghoneim¹,

Al-Khaldi²,

Elsherif³

et al. 2021

Preprint

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This dissertation presents a method for the synthesis of substituted indoles bearing heterocyclic substituents onto the 3- position. The route for the synthesis of the heterocyclic substituents indoles starts from 3-acetyl indole nucleus depend on two parts. One part: Reaction of 3-acetylindole 1 with hydrazide compounds such as phenyl hydrazine, hydrazine hydrate, and thio-semicarbazide, to yield 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2, 3-(1-hydrazonoethyl)-1H-indole 6, and thiosemicarbazone 10 respectively. 3-(1-Hydrazonoethyl)-1H-indole 6 reacted with thiophene-2-carboxaldeyde, isatin and 3-acetyl indole. In the same way, 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2 reacted with thioglycollic acid, glycine and benzaldehyde. 3-Acetylindole 1 thiosemicarbazone reacted with acetic anhydride, piperidine, concentration of hydrochloric acid and thiophene-2-carboxaldeyde. Second part. Reaction of 3-acetyl indole 1 with amines compounds such as p-nitroaniline to formed Schiff base 15 which it reacted with thioglycollic acid to give compound 16. 3-Acetyl indole 1 reacted with ethylene diamine to afford bis imine indole to afford compound 17. The reports of this docking study revealed that the new compounds exhibit good antibacterial activity. The synthesized compounds screened in vitro for their antibacterial activity revealed remarkable inhibitory effects against the selected microorganisms. And also an anti-oxidant activity studying for some synthesized compounds. Structures of the newly synthesized compounds examination by spectral data (IR, 1H- NMR and 13C -NMR).

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Section: Methodsmentioning

confidence: 99%

Construction, Molecular Docking, Antimicrobial and Antioxidant Activity of Some Novel 3-Substitued Indole Derivatives Using 3-Acetyl Indole

Ghoneim¹,

Al-Khaldi²,

Elsherif³

et al. 2021

Preprint

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“…Substituted thiosemicarbazides (TSCs) constitute an important class of organic compounds with the general formula R-(C O)-NH-NH-(C S)-R 0 and find application in the synthesis of five-and six-membered heterocyclic compounds (Gazieva & Kravchenko, 2012) and transition-metal complexes (Campbell, 1975). The chemical diversity of thiosemicarbazides, and their synthesis, including their role in biological applications, is nicely summarized in a recent review article (Acharya et al, 2021).…”

Section: Chemical Contextmentioning

confidence: 99%

Structural investigation of N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide and N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide

Dey¹,

Shruti²,

Chopra³

et al. 2021

Acta Cryst E

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The compound N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide, C21H16FN3O3S, crystallizes in the monoclinic centrosymmetric space group P21/c and its molecular conformation is stabilized via an intramolecular N—H...O hydrogen bond. The corresponding para-methoxy derivative, namely, N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide, C22H18FN3O4S, crystallizes in the monoclinic centrosymmetric space group C2/c. The supramolecular network mainly comprises N—H...O, N—H...S and C—H...O hydrogen bonds, which contribute towards the formation of the crystal structures for the two molecules. The different intermolecular interactions have been further analysed using Hirshfeld surface analysis and fingerprint plots.

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“…Over decades, thiosemicarbazides are evidenced to be effective intermediates for the development of so many pharmaceutical and bioactive materials and hence, they are applied expandly in medicinal chemistry. The vast number of heterocycles produced from thiosemicarbazides is related primarily to the fact that these compounds can display the characteristics of N(1)-; N(2)-; N(1); N(4)-; N (2); N(4)-; N(1); S-, N(2); S-and N(4),S-nucleophiles [20]. Among of these heterocycles are the thiosemicarbazones derivatives with isatin counterparts that have attracted the concern of the pharmacy world owing to their extensive range of biological features [21][22][23] and industrial application as corrosion inhibitors [24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Evolution of the Efficiency of Divalent Cobalt and Copper Chelates Based on Isatin Derivatives and Thiosemicarbazide Ligands as Inhibitors for the Corrosion of Sabic Iron in Acidic Medium

El‐Ghamry

Fawzy

Farghaly

et al. 2021

Preprint

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Divalent cobalt and copper chelates of the two ligands 1-(1- Ethoxycarbonylmethyl-2-oxoindolin-3-ylidene) thiosemicarbazide (EOIT) and 1-(1-Benzyl-2-oxoindolin-3-ylidene) thiosemicarbazide (BOIT) are the target compounds of the current study. Identification of the constitution and geometry of these compounds have been performed using the possible physicochemical and analytical instruments. Elemental analysis, molar conductance and thermal analysis assured the composition of the four chelates to be [Co(POIT)Cl]•1.5H2O, [Cu(POIT)Cl], [Co(BOIT)Cl2(H2O)]•5H2O and [Cu(BOIT)Cl]•Cl which was further confirmed by the measurement of mass spectra. The architecture arrangement of the ligand atoms around Co and Cu centers has been determined depending on the UV-Vis spectral measurements and calculation of µeff values assuring the copper compounds to be square plane whereas the cobalt complexes have tetrahedral or octahedral arrangements. These compounds were examined as corrosion inhibitors for the Sabic steel in 1.0 M HCl utilizing potentiodynamic polarization, electrochemical impedance spectroscopy, mass-loss method and scanning electron microscopy at fixed temperature of 298 K. The acquired outcomes disclosed that the inhibition efficiencies (% IEs) of the examined compounds were set to be dependent on both the concentrations and composition of the compounds. The examined compounds were set to have high % IEs, which were interpreted by strong adsorption of the compounds’ molecules on the iron surface and such adsorption was discovered to follow Langmuir adsorption isotherm. The investigational results obtained from all utilized techniques were set to be in a good accord with each other.

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Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds

Cited by 46 publications

References 52 publications

Construction, Molecular Docking, Antimicrobial and Antioxidant Activity of Some Novel 3-Substitued Indole Derivatives Using 3-Acetyl Indole

Construction, Molecular Docking, Antimicrobial and Antioxidant Activity of Some Novel 3-Substitued Indole Derivatives Using 3-Acetyl Indole

Structural investigation of N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide and N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide

Evolution of the Efficiency of Divalent Cobalt and Copper Chelates Based on Isatin Derivatives and Thiosemicarbazide Ligands as Inhibitors for the Corrosion of Sabic Iron in Acidic Medium

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