Antioxidant properties of some thiourea derivatives

Antioxidant properties of some thiourea derivatives in model reactions were studied.     

Synthesis and biological applications of some novel 8-Hydroxyquinoline urea and thiourea derivatives

A number of novel urea and thiourea derivatives of 8-hydroxyquinoline have been designed, synthesized and evaluated for their anticancer activities. The structures of the new compounds were established by spectroscopic techniques, ¹H NMR, ¹³C NMR, and mass spectrometry. The in vitro cytotoxicity against MCF7, and MDA-MB-231 cell lines were assessed by MTT assay. Six of the 11 compounds synthesized namely 5b, 5c, 5f, and 6b-d exhibited cytotoxicity with IC₅₀ values ranged between 0.5 and 42.4 µM. Apoptotic features of cells treated with 5b compound were observed via florescent microscopy using DAPI and ethidium bromide/acridine orange staining against MCF-7 cells. Molecular docking of these molecules against 16 potential breast cancer protein revealed that these compounds could interact with the active site of poly (ADP-ribose) polymerase-1 (PARP1), B-cell lymphoma-extra large (Bcl-xL) and PARP5A (Tankyrase 1) by forming hydrogen bonds, π-π interactions and hydrophobic interactions. The docked poses of these molecules were observed to be similar in the active site of each of these targets.     

Synthesis and bioactivity of pyrazole acyl thiourea derivatives

Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, 1H-NMR, 13C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.     

Synthesis of thiourea derivatives as CCR4 antagonists

A series of thiourea derivatives have been synthesized. Their structures were confirmed by MS and 1H NMR. Several compounds showed potent activities as antagonists of CCR4 receptor.     

Synthesis and dual binding character of novel macrocyclic thiourea derivatives

Novel macrocyclic thiourea derivative was synthesized, and their ambident binding ability toward dihydrogenphosphate anion and several cations was evaluated by NMR titration and Meisenheimer test.     

Synthesis and transformation of N-oxides of some imidazo[4,5-b]pyrazine derivatives

The Böckelheide reaction was accomplished with a number of imidazo[4,5-b]pyrazine N-oxides, and the N-oxidation of the resulting acetoxy(hydroxy)methyl derivatives of imidazo[4,5-b]pyrazine and 6-bromo-1-methylimidazo[4,5-b]pyrazine was studied. The hydrolytic cleavage of 6-bromo-1-methylimidazo[4,5-b]pyrazine and its 4-N-oxide was studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 690–693, May, 1975.     

Synthesis, spectroscopic properties and antipathogenic activity of new thiourea derivatives

A number of acylthioureas, 2-((4-methylphenoxy)methyl)-N-(aryl-carbamothioyl)benzamides (aryl = 3,5-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichloro-phenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2-bromophenyl, 2,4-dibromophenyl, 2,5-dibromophenyl, 2-iodophenyl, 3-fluorophenyl, 2,3,4-trifluorophenyl, 2,4,5-trifluoro-phenyl, 2,4,6-trifluorophenyl) have been synthesized, characterized by elemental analysis, IR and NMR spectroscopy and tested for their interaction with bacterial cells in free and adherent state. The anti-pathogenic activity was correlated with the presence of one iodine, bromide or fluorine, and two or three chloride atoms on the N-phenyl substituent of the thiourea moiety, being significant especially on Pseudomonas aeruginosa and Staphylococcus aureus strains, known for their ability to grow in biofilms. Our results demonstrate the potential of these derivatives for further development of novel anti-microbial agents with antibiofilm properties.     

Adsorptive stripping voltammetric determination of thiourea and thiourea derivatives

Adsorptive stripping voltammetry of thiourea, α-naphthylthiourea and diphenyl-thiourea is discussed. In perchlorate solution, these compounds are adsorbed at the hanging mercury drop electrode at positive potentials (or at open circuit) and can be stripped in a cathodic scan. Detection limits are 2.5 ng l^?1 for thiourea, 80 ng l^?1 for α-naphthylthiourea and 50 ng l^?4 for diphenylthiourea. The method is applicable in the determination of thiourea in cattle-feed and in the direct analysis of urine.     

Synthesis of some heptazine derivatives

Chemistry of Heterocyclic Compounds - New derivatives of heptazine were prepared from 2,5,8-trichloroheptazine by a Friedel–Crafts reaction and Pd-catalyzed amination. New...     

Synthesis of some thienopyrimidine derivatives

Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolo-pyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.     

Synthesis of some L-idose derivatives

The synthesis of 3-0-benzyl- and 3-0-mesyl-1,2-0-isopropylidene-β′-L-iodofuranose has been effected on the basis of the intramolecular nucleophilic exchange of a mesyloxy group at C₅ in derivatives of 1,2-0-isopropylidene-α-D-glucofuranose. It has been found that in a system of vicinal primary and secondary mesyloxy groups a selective replacement of the primary mesyloxy group by an acetyl group is possible. It has been shown in benzyl and mesyl ethers of 5,6-anhydro-1,2-0 -isopropylidene-β-L-idofuranose the opening of the oxide ring under conditions of acid hydrolysis with the retention of the isopropylidene group is possible.     

Synthesis of some crotonic derivatives

Summary Eight previously undescribed dicrotonic derivatives were synthesized. Synthesis was by the reaction of hexamethylene and 2,4-tolylene diisocyanates with crotonic acid, crotonamide, N-(hydroxymethyl)crotonamide, and N -2-hydroxyethylcrotonamide.     

Synthesis of some phenanthridone derivatives

The alkylation of phenanthridone and some nuclear-substituted phenanthridones using sodium hydride in DMF/benzene is reported. Various 5-cyanoalkylphenanthridones were converted to further derivatives by either hydrolysis or reduction.     

Synthesis of some thiophene derivatives

The synthesis of thiopene derivatives from diacetylenic hydrocarbons has been described [1]. We have examined for the first time the reaction of diacetylenic diesters with hydrogen sulfide and with NaHS. The diacetylenic diesters react readily with hydrogen sulfide or NaHS in acetone at pH 9–10 to give 2,5-disubstituted thiopheries (see Table 1).Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 713–714, May, 1970.     

Synthesis of some sym-triazole derivatives

3,5-Di(hydroxyalkyl) derivatives of 4-amino-1,2,4-triazole and the corresponding derivatives of 1,2,4-triazole obtained by diazotizing them are converted by reaction with SOCl₂ into the hydrochlorides of 4-amino-3,5-di(chloroalkyl)-1,2,4-triazoles and 3,5-di(chloroalkyl)-1, 2,4-triazoles. The dinitrate of 3,5-di(hydroxymethyl)-1,2,4-triazole has been prepared. When the cyanohydrazide of glycolic acid is heated with hydrazine hydrate, 4,5-diamino-3-hydroxymethyl-1, 2,4-triazole is formed.     

Synthesis and characterization of some single crystals of thiourea urea zinc chloride

Thiourea Urea Zinc (II) Chloride (TUZC), a new semiorganic non-linear optical material has been synthesized. The solubility studies have been carried out at room temperature. Single crystals of different proportions of TUZC have been grown by slow evaporation of saturated aqueous solution at room temperature. The FTIR and UV spectral bands have been compared with urea, thiourea and bis Thiourea Zinc Chloride (BTZC). The TG curve showed a two steps mass loss on heating the compound between 30 and 800 °C corresponding to two exothermic DTA peaks at 181–183 and 250–252 oC.     

Synthesis and evaluation of urea and thiourea derivatives of oxazolidinones as antibacterial agents

Urea and thiourea derivatives of oxazolidinones were synthesized and their inhibitory activity (MIC) was determined on the bacterial strains which includes clinical isolates and quality control organisms. The structure activity relationships were studied and a 3D-QSAR model was built using Genetic Function Approximation. Interestingly found that electron withdrawing groups at the ortho position of the phenyl ring enhances the activity.