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1.
Bioorg Chem ; 89: 102998, 2019 08.
Artigo em Inglês | MEDLINE | ID: mdl-31128819

RESUMO

In this study, novel imidazo[2,1-b][1,3,4]thiadiazole (ITD) compounds were synthesized and their antimicrobial and antioxidant capacity was examined. The C-2 position of the ITD structure was fixed with the 3,4-hydroxybenzene ring and the properties of the two series of compounds obtained by phenyl or 4-chlorophenyl in the C-6 position were compared. In the formation of these series, new properties were determined by the addition of different pharmacophore to the target product by binding of the groups known in the literature from the C-5 position to the structure. In the study, it was seen that the compounds 4a, 4b, 5a, 5b, 7f, 10, 12 and 13 had very high anti-tuberculosis activities at low concentrations, 3b was found to exhibit moderate activity while other synthesis compounds exhibited moderate activity. In addition, it showed activity against gram positive and negative bacteria. In the determination of the antioxidant capacities of the newly synthesized compounds by FRAP and DPPH methods, the compounds showing activity were found to be 2, 3a, 3b, 6c, 9, 11 and 13. The structures of all synthesized compounds were solved by spectroscopic methods such as FT-IR, 1H NMR, 13C NMR and mass.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Desenho de Fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Imidazóis/farmacologia , Tiadiazóis/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Relação Dose-Resposta a Droga , Recuperação de Fluorescência Após Fotodegradação , Imidazóis/síntese química , Imidazóis/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade , Tiadiazóis/síntese química , Tiadiazóis/química
2.
Bioorg Chem ; 88: 102928, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31005785
3.
Spectrochim Acta A Mol Biomol Spectrosc ; 133: 272-80, 2014 Dec 10.
Artigo em Inglês | MEDLINE | ID: mdl-24952089

RESUMO

In this study, novel phthalonitrile derivative (3) was synthesized by the reaction between 4-nitrophthalonitrile (2) and a triazole derivative (1) containing pyridine moiety. Crystal structure of compound (3) was characterized by X-ray diffraction. New metal free and metallo-phthalocyanine complexes (Zn, Cu, and Mg) were synthesized using the phthalonitrile derivative (3). Cationic derivatives of these phthalocyanines (5, 7, 9, and 11) were prepared from the non-ionic phthalocyanines (4, 6, 8, and 10). All proposed structures were supported by instrumental methods. The aggregation behaviors of the phthalocyanines (4-11) were investigated in different solvents such as dimethylsulfoxide (DMSO), N,N-dimethylformamide (DMF), chloroform and water. Water soluble cationic Pcs (5, 7, 9, and 11) aggregated in water and sodium dodecyl sulfate was used to prevent the aggregation. The second derivatives of the UV-Vis spectra of aggregated Pcs were used for analyzing the Q and B bands of aggregated species. Thermal behaviors of the phthalocyanines were also studied. In addition, anti-bacterial properties of the phthalocyanines were investigated. We used four gram negative and two gram positive bacteria to determine antibacterial activity of these compounds. Compound 7 has the best activity against the all bacteria with 125µg/mL of MIC value. Compounds 4, 6, and 10 have the similar effect on the bacteria with 250µg/mL of MIC value.


Assuntos
Antibacterianos/química , Cobre/química , Indóis/química , Magnésio/química , Compostos Organometálicos/química , Zinco/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Infecções Bacterianas/tratamento farmacológico , Cobre/farmacologia , Cristalografia por Raios X , Humanos , Indóis/farmacologia , Isoindóis , Magnésio/farmacologia , Modelos Moleculares , Compostos Organometálicos/farmacologia , Solubilidade , Água/química , Zinco/farmacologia
4.
Bioorg Khim ; 40(3): 341-56, 2014.
Artigo em Inglês | MEDLINE | ID: mdl-25898742

RESUMO

1,2,4-Triazole-3-one prepared from tryptamine was converted to the corresponding carbotioamides by several steps. Their treatment with ethyl bromoacetate or 4-chlorophenacyl bromide produced the corresponding 5-oxo-1,3-thiazolidine or 3-(4-chlorophenyl)-1,3-thiazole derivatives. Acetohydrazide derivative that was obtained starting from tryptamine, was converted to the corresponding Schiff basis and sulfonamide by the treatment with suitable aldehydes and benzensulphonyl chloride, respectively. 2-[(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl)methyl]-4-[2-(1H-indole-3-yl)ethyl]-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one was synthesized starting from hydrazide via the formation of the corresponding 1,3,4-oxadiazole compound, while the other bitriazole compounds were obtained by intramolecular cyclisation of carbothioamides in basic media. The treatment of 1,2,4-triazole or 1,3,4-oxadiazole compound with several amines generated the corresponding Mannich bases. Ethyl (2-amino-1,3-thiazole-4-yl)acetate was converted to the corresponding 1,3,4-oxadiazole derivative, arylidenehydrazides, 1,2,4-triazole-3-one and 5-oxo-1,3-oxazolidine derivatives by several steps. The structural assignments of new compounds were based on their elemental analysis and spectral (FT IR, 1H NMR, 13C NMR and LC-MS) data. The antimicrobial, antilipase and antiurease activity studies revealed that some of the synthesized compounds showed antimicrobial, antilipase and/or antiurease activity.


Assuntos
Anti-Infecciosos/síntese química , Oxidiazóis/síntese química , Triazóis/síntese química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , Lipase/antagonistas & inibidores , Bases de Mannich/síntese química , Bases de Mannich/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Oxidiazóis/química , Oxidiazóis/farmacologia , Relação Estrutura-Atividade , Triazóis/química , Triazóis/farmacologia , Urease/antagonistas & inibidores
5.
Arch Pharm (Weinheim) ; 346(10): 743-56, 2013 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-24038519

RESUMO

4-Aryl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-(thi)oles 5-7, obtained starting from nicotinic acid hydrazide were converted to the corresponding Mannich bases 12-24 by the reaction with several heterocyclic amines in the presence of formaldehyde. The synthesis of S-alkylated compounds 8-11 was performed from the reaction of the corresponding triazol-5-thioles with various alkyl halides. The condensation of carbo(thio)amides 2-4 with 4-chlorophenacyl bromide afforded the corresponding 1,3-thia(oxa)zol-2(3H)-ylidene]pyridine-3-carbohydrazides 25-27. 1,3-Thia(oxa)zolidine derivatives 28-30 were obtained from the cyclization reaction between compounds 2-4 and ethyl bromoacetate. All newly synthesized compounds were screened for their antimicrobial, antiurease, and antilipase activities. The biological activity studies revealed that all the compounds screened showed good or moderate antimicrobial, antiurease, and/or antilipase activity.


Assuntos
Anti-Infecciosos/farmacologia , Lipase/antagonistas & inibidores , Triazóis/farmacologia , Urease/antagonistas & inibidores , Anti-Infecciosos/síntese química , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Compostos Heterocíclicos/síntese química , Compostos Heterocíclicos/química , Compostos Heterocíclicos/farmacologia , Bases de Mannich/síntese química , Bases de Mannich/química , Bases de Mannich/farmacologia , Triazóis/síntese química , Triazóis/química
6.
Eur J Med Chem ; 67: 230-42, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23871903

RESUMO

Norfloxacin was converted to 7-(4-amino-2-fluorophenyl)piperazin derivative (2) via the formation of nitro compound. The synthesis of the norfloxacin derivatives containing 1,3-thiazole or 1,3-thiazolidin moiety was performed from the reaction of 4-chlorophenacylbromide or ethyl bromoacetate with compounds 4-7 obtained starting from 2. 3-Fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]aniline (14), 5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol (18) and {[4-(2-methoxy phenyl)piperazin-1-yl]methyl}-1,3,4-oxadiazol-2-thiol (19) were obtained starting from 1-(2-methoxyphenyl)piperazine by several steps. The treatment of hydrazide (16) with several aldehydes afforded N'-[(2-hydroxyphenyl)methylen]- (20), N'-[(3-hydroxy-4-methoxy phenyl)methylen]- (21) or N'-[1H-indol-3-ylmethylene]-2-[4-(2-methoxyphenyl)piperazin-1-yl]acetohydrazide (22). Then, compounds 14, 18, 19 and 22 were condensed with 7-[4-(chloroacetyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3) that was obtained from norfloxacine. All newly synthesized compounds were screened for their antimicrobial activities and some of them exhibited excellent activity. Moreover, one compound was found to have antiurease activity.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Inibidores Enzimáticos/farmacologia , Micro-Ondas , Norfloxacino/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Bactérias/efeitos dos fármacos , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Norfloxacino/síntese química , Norfloxacino/química , Relação Estrutura-Atividade , Urease/antagonistas & inibidores , Urease/metabolismo
7.
Eur J Med Chem ; 45(11): 4726-32, 2010 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-20727622

RESUMO

Acetohydrazide derivative containing both antipyrine and triazole nuclei (5) was obtained starting from ethyl hydrazinecarboxylate derivative (2) and 4-aminoantipyrine (1) by three steps. The treatment of compound 5 with CS(2) afforded the conversion of hydrazide function into 5-mercapto-1,3,4-oxadiazole ring leading to the formation of 7. Then, 7 gave the product containing triazolotriazine moiety (9) by the reaction with hydrazine hydrate. The synthesis of the compounds incorporating the 1,3,4-thiadiazole (10a-c), 1,2,4-triazole (11a-c) or 1,3-thiazole (12, 13) nucleus as third heterocycle was performed by the acidic or basic treatment of compounds 6a-c which were obtained from the reaction of 5 with several isothiocyanates, or by the condensation of 6a with two different phenacyl bromides, respectively. The antimicrobial activity study revealed that all the compounds showed good activities except 3-5.


Assuntos
Anti-Infecciosos/farmacologia , Antipirina/química , Triazóis/química , Anti-Infecciosos/química , Ciclização , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Espectrofotometria Infravermelho
8.
Eur J Med Chem ; 44(11): 4362-6, 2009 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-19647352

RESUMO

5-Pyridin-4-yl-1,3,4-oxadiazole-2-thiol (2) was obtained from the reaction of isonicotinic acid hydrazide with carbon disulfide in basic media and converted into 4-amino-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (5) by the treatment with hydrazine hydrate. The synthesis of 3 and 6 was performed from the reaction of 2 and 5 with ethyl bromide. The treatment of 5 with 4-fluorobenzaldehyde or indol-3-carbaldehyde resulted in the formation of 4-[(arylmethylene)amino]-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiols (7a and 7b). The reactions of 2, 5 and 7a with some primary and secondary amines in the presence of formaldehyde afforded the corresponding Mannich bases, 4a, 4b, 9a-9c and 8. All newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that all the compounds screened showed good or moderate activity except compounds 2, 7a, 7b, 8 and 9b.


Assuntos
Anti-Infecciosos/síntese química , Anti-Infecciosos/farmacologia , Isoniazida/análogos & derivados , Triazóis/síntese química , Triazóis/farmacologia , Anti-Infecciosos/química , Bactérias/efeitos dos fármacos , Bases de Mannich , Testes de Sensibilidade Microbiana , Estrutura Molecular , Oxidiazóis/síntese química , Oxidiazóis/química , Oxidiazóis/farmacologia , Relação Estrutura-Atividade , Triazóis/química , Leveduras/efeitos dos fármacos
9.
Eur J Med Chem ; 44(3): 1057-66, 2009 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-18676062

RESUMO

4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (3) was obtained in basic media via the formation of 2-isonicotinoyl-N-phenylhydrazinecarbothioamide (2), and converted to some alkylated derivatives (4a,b) and Mannich base derivatives (5a-c). 2-[(4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]acetohydrazide (7) that was obtained by using compound 3 as precursor in two steps was converted to thiosemicarbazide derivative (8), Schiff base derivatives (9) and 5-{[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-1,3,4-oxadiazole-2-thiol (10). Moreover, 5-{[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-3-{[(2-morpholin-4-ylethyl)amino]methyl}-1,3,4-oxadiazole-2(3H)-thione (11) was synthesized via reaction of compound 10 with 2-(4-morpholino)ethylamine. The treatment of compound 8 with NaOH gave 4-(4-methylphenyl)-5-{[(4-phenyl-5-pyridine-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-4H-1,2,4-triazole-3-thiol (12), while the acidic treatment of compound 8 afforded 5-{[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]methyl}-2(4-methylphenyl)-amino-1,3,4-thiadiazole (14). N-Methyl derivative of compound 14 and a Mannich base derivative of compound 12 were synthesized from the reactions of these precursors with methyl iodide and methyl piperazine, respectively. All newly synthesized compounds were screened for their antimicrobial activities. The antimicrobial activity study revealed that all the compounds screened showed good or moderate activity except compounds 3, 5c, 7, 9c, 9e, 9g, 9h, 11, and 13.


Assuntos
Anti-Infecciosos/síntese química , Bases de Mannich/química , Bases de Schiff/química , Triazóis/síntese química , Anti-Infecciosos/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Espectrofotometria Infravermelho , Triazóis/farmacologia
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