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1.
Artigo em Inglês | MEDLINE | ID: mdl-38265284

RESUMO

The novel N-naphthylcyanoacrylamide thioglycosides 4 were readily prepared by the reaction of N-napthylcyanoacetamide 1 with aryl isothiocyanates in the presence of potassium hydroxide, followed by coupling of the produced salts 2 with 2,3,4,6-tetra-O-acetyl-α-d-gluco- and galacto-pyranosyl bromides 3. The N-naphthyl acrylamide thioglycoside 12 was prepared by the reaction of N-napthylcyanoacetamide 1 with glucose isothiocyante 10 in the presence of potassium hydroxide, followed by alkylation of the produced salt 11 with methyl iodide. The reaction of thioglycoside compounds 4 with hydrazines afforded the corresponding naphthyl-pyrazole hybrids.

2.
Nucleosides Nucleotides Nucleic Acids ; 39(8): 1134-1149, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32600173

RESUMO

This research reports a novel method for synthesizing a new class of indeno[1,2-b]pyridine thioglycosides. This series of indenopyridine thioglycosides was designed by the reaction of (E)-2-cyano-3-(furan/or thiophene-2-yl)prop-2-enethioamide 1a or 1b with 1-indanone 2 to give the corresponding 2-thiooxo-1H-indeno[1,2-b]pyridine-3-carbonitriles 3a,b. The latter compounds were treated with peracetylated sugar bromides 5 in KOH-acetone to give the corresponding indenopyridine thioglycosides 6a-h. Ammonolysis of the protected indenopyridine thioglycosides 6a-h gave the corresponding free indenopyridine thioglycosides 7a-h. The compounds have been characterized by 13C NMR, 1H NMR and IR spectra.


Assuntos
Desenho de Fármacos , Piridinas/síntese química , Tioglicosídeos/síntese química , Estrutura Molecular , Piridinas/química , Tioglicosídeos/química
3.
Nucleosides Nucleotides Nucleic Acids ; 37(3): 186-198, 2018 Mar 04.
Artigo em Inglês | MEDLINE | ID: mdl-29608403

RESUMO

A novel series of acyclic pyridine thioglycosides has been synthesized. Evaluation of the anti proliferative activity of these compounds against HEPG-2 cell lines (liver carcinoma cell lines) shows that most of the compounds have high anti-tumor activities especially 6b, 6c, 7b and 7c. Furthermore, in the modeling study, these compounds showed that they have high binding affinity with thymidylate synthase dihydrofolate reductase (TS-DHFR).


Assuntos
Antineoplásicos/síntese química , Carcinoma Hepatocelular/tratamento farmacológico , Neoplasias Hepáticas/tratamento farmacológico , Piridinas/síntese química , Tioglicosídeos/síntese química , Antineoplásicos/uso terapêutico , Sítios de Ligação , Carcinoma Hepatocelular/patologia , Sobrevivência Celular/efeitos dos fármacos , Desenho de Fármacos , Células Hep G2 , Humanos , Neoplasias Hepáticas/patologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Complexos Multienzimáticos/metabolismo , Ligação Proteica , Piridinas/uso terapêutico , Relação Estrutura-Atividade , Tetra-Hidrofolato Desidrogenase/metabolismo , Tioglicosídeos/uso terapêutico , Timidilato Sintase/metabolismo
4.
Nucleosides Nucleotides Nucleic Acids ; 36(7): 474-495, 2017 Jul 03.
Artigo em Inglês | MEDLINE | ID: mdl-28613111

RESUMO

New [(Indolyl)pyrazolyl]-1,3,4-oxadiazole compounds and their derived thioglycosides as well as the corresponding sugar hydrazones were synthesized. The acyclo C-nucleoside analogs of the oxadiazoline base system were also prepared by reaction of acid hydrazides with aldehydo sugars followed by one pot process encompassing acetylation and cyclization of the synthesized hydrazones. The anticancer activity of the newly synthesized compounds was studied against colorectal carcinoma (HCT116), breast adenocarcinoma (MCF7) and prostate cancer (PC3) human tumor cell lines and a number of compounds showed moderate to high activities.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Nucleosídeos/química , Oxidiazóis/química , Tioglicosídeos/síntese química , Tioglicosídeos/farmacologia , Antineoplásicos/química , Antineoplásicos/metabolismo , Domínio Catalítico , Linhagem Celular Tumoral , Quinase 2 Dependente de Ciclina/química , Quinase 2 Dependente de Ciclina/metabolismo , Ciclização , Humanos , Simulação de Acoplamento Molecular , Relação Estrutura-Atividade , Tioglicosídeos/química , Tioglicosídeos/metabolismo
5.
Nucleosides Nucleotides Nucleic Acids ; 36(5): 355-377, 2017 May 04.
Artigo em Inglês | MEDLINE | ID: mdl-28387606

RESUMO

A convenient synthesis of a novel series of dihydropyridine and pyridine thioglycosides was developed. The evaluation of anti-proliferative activity against HepG-2 cell lines (liver carcinoma cell lines) shows that most of the compounds have antitumor activity, especially 5b, 5f, 5j, 5n, 7b, 7f, 7j, 7n, 8b, 8f, and 8j. The results of molecular docking reveal that these compounds have high binding affinity by hydrogen bond formation with the binding pocket of thymidylate synthase dihydrofolate reductase (TS-DHFR).


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Desenho de Fármacos , Piridinas/química , Piridinas/farmacologia , Tioglicosídeos/química , Tioglicosídeos/farmacologia , Antineoplásicos/síntese química , Proliferação de Células/efeitos dos fármacos , Di-Hidropiridinas/síntese química , Di-Hidropiridinas/química , Di-Hidropiridinas/farmacologia , Células Hep G2 , Humanos , Fígado/efeitos dos fármacos , Fígado/metabolismo , Neoplasias Hepáticas/tratamento farmacológico , Neoplasias Hepáticas/metabolismo , Simulação de Acoplamento Molecular , Complexos Multienzimáticos/metabolismo , Ligação Proteica , Piridinas/síntese química , Tetra-Hidrofolato Desidrogenase/metabolismo , Tioglicosídeos/síntese química , Timidilato Sintase/metabolismo
6.
Acta Crystallogr Sect E Struct Rep Online ; 66(Pt 5): m554-5, 2010 Apr 21.
Artigo em Inglês | MEDLINE | ID: mdl-21579039

RESUMO

In the title compound, [Ca(C(18)H(15)N(2)O(3)S(2))(H(2)O)(4)]·2C(4)H(10)O, the Ca atom, which lies on an inversion centre, is coordinated octa-hedrally by four water mol-ecules and two anions of the ketene dithio-acetal, the donor atoms of which are the amidic carbonyl O atoms. The central backbone of the ligands (excluding the naphthalene and oxoethyl groups) is essentially planar (r.m.s. deviation 0.035 Å). Intra-molecular hydrogen bonds are observed from the NH group to the formally 'thiol-ate' S atom and from one coordinated water to the nitrile group and to the ether O atom. Inter-molecular hydrogen bonds from the second independent water mol-ecule to the thiol-ate S atom and the side-chain oxo group connect the mol-ecules in chains parallel to the a axis.

7.
Eur J Med Chem ; 45(3): 973-82, 2010 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-20004044

RESUMO

A number of a new pyridine thioglycosides were synthesized via reaction of piperidinium salts of dihydropyridinethiones with 2,3,4,6-tetra-O-acetyl-alpha-D-gluco- and galactopyranosyl bromide. The antitumor activities of the synthesized compounds were evaluated utilizing two different human cell lines. Some of the tested compounds showed high inhibition of human cell lines. The detailed synthesis, spectroscopic data and antitumor activities for the synthesized compounds were reported.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Di-Hidropiridinas/síntese química , Di-Hidropiridinas/farmacologia , Tioglicosídeos/síntese química , Tioglicosídeos/farmacologia , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Di-Hidropiridinas/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidrogenação , Masculino , Camundongos , Estrutura Molecular , Neoplasias/tratamento farmacológico , Tioglicosídeos/química
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