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1.
Bioorg Chem ; 101: 103932, 2020 08.
Artículo en Inglés | MEDLINE | ID: mdl-32506019

RESUMEN

There is an urging continuous need for novel anti-cancer agents due to persistent chemoresistance. Herein, newly synthesized cinnolines are evaluated for their possible anticancer activities and suggested mechanisms. In the current study, a simple and efficient synthesis of densely functionalized cinnolines has been developed that relied on multi-component reaction of ethyl 5-cyano-4-methyl-1-aryl-6-oxo-1,6-dihydropyridazine-3-carboxylates with aromatic aldehydes and nitromethane in dioxane/pipridine under controlled microwave heating. Selected cinnolines (4a-c, e, h, j-n, q-v) were tested for possible anticancer activity using in vitro one dose assay at National Cancer institute, USA. Only cinnoline 4b stood out as the most potent cinnoline derivative (mean GI%=26.33) with broad-spectrum antitumor activity against the most tested cancer cell lines from all subpanels. The target cinnoline 4b emerged as the most active derivative against both leukemia RPMI-8226 and melanoma LOX IMVI cell lines (GI% = 106.06 and 82.1) respectively, with IC50 values equal to 17.12 ± 1.31 and 12.32 ± 0.75 µg/mL, which are comparable to those of staurosporin; 24.97 ± 1.47 and 8.45 ± 0.42 µg/mL, respectively. Cinnoline 4b influenced cell cycle distribution causing pre-G1 apoptosis and cell growth arrest at G2/M phase. It also induced apoptosis in both cell lines as manifested by significant increase in the percent of annexin V-FITC positive apoptotic cells in leukemia RPMI-8226 cells (from 1.09% to 12.47%) and melanoma LOX IMVI (from 1.32% to 19.05%). In addition, it showed lower expression levels of anti-apoptotic Bcl-2 protein, and higher expression levels of pro-apoptotic proteins; Bax, p53, cytochrome c, caspases 3 and 9. CONCLUSION: Induction of mitochondrial intrinsic pathway of apoptosis is a possible mechanism by which cinnoline 4b may confer its anticancer activity.


Asunto(s)
Antineoplásicos/farmacología , Apoptosis/efectos de los fármacos , Compuestos Heterocíclicos con 2 Anillos/síntesis química , Compuestos Heterocíclicos con 2 Anillos/farmacología , Microondas , Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Humanos , Mitocondrias/efectos de los fármacos
2.
Beilstein J Org Chem ; 16: 1706-1712, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32733614

RESUMEN

An efficient one-pot synthesis of N 2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine-2,4-diamine derivatives was developed by reacting 5-amino-1,2,3,4-tetrazole with aromatic aldehydes and cyanamide in pyridine under controlled microwave heating with high yields. X-ray crystallography confirmed the structure of the obtained products.

3.
Mol Divers ; 23(4): 1065-1084, 2019 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-30666490

RESUMEN

α-Cyanoketones represent a synthetically attractive scaffold possessing bifunctional reactivity which enabled synthesis of a diversity of products. This involves reaction of nucleophiles with electrophilic carbonyl carbon performing an efficient and regioselective way to acylation reaction, cycloaddition of activated cyano function with dipolarophiles, metal-catalyzed cross-dehydrogenative coupling carbocyanation across C-C multiple bonds as well as hydrocyanation. This review provides the recent developments in the chemistry of α-cyanoketones which will be beneficial for researchers and scientists in such field.


Asunto(s)
Cianuros/química , Compuestos Heterocíclicos/síntesis química , Acilación , Reacción de Cicloadición
4.
Molecules ; 23(3)2018 Mar 09.
Artículo en Inglés | MEDLINE | ID: mdl-29522435

RESUMEN

A convenient, fast and environmentally benign procedure for the synthesis of a new series of highly functionalized N-alkylated pyridines as privileged medicinal scaffolds was developed via a unique three-component reaction of easily available aromatic as well as heteroaromatic aldehydes, N-alkyl-2-cyanoacetamides and malononitrile in EtOH in the presence of K2CO3 as a base promoter under microwave irradiation. The presented tandem process is presumed to proceed via Knoevenagel condensation, Michael addition, intramolecular cyclization, autoxidation and subsequent aromatization. Particularly valuable features of this protocol, including high product yields, mild conditions, atom-efficiency, simple execution, short reaction times and easy purification make it a highly efficient and promising synthetic strategy to prepare substituted pyridine nuclei. The proposed mechanism of this novel one-pot reaction and structure elucidation of the products are discussed.


Asunto(s)
Aldehídos/química , Técnicas de Química Sintética , Microondas , Nitrilos/química , Piridinas/síntesis química , Piridinas/química
5.
Mol Divers ; 19(3): 625-51, 2015 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-25894364

RESUMEN

Developments made since 2010 in the utilization of multi-component reactions as green efficient methodologies for the synthesis of polysubstituted pyrans, thiopyrans, pyridines, and pyrazoles are reviewed and the mechanisms of these processes are discussed. Reference is made to classical older synthetic methods developed earlier in our laboratories.


Asunto(s)
Técnicas de Química Sintética/métodos , Tecnología Química Verde/métodos , Piranos/síntesis química , Pirazoles/síntesis química , Piridinas/síntesis química , Compuestos de Sulfhidrilo/síntesis química , Piranos/química , Pirazoles/química , Piridinas/química , Compuestos de Sulfhidrilo/química
6.
Molecules ; 19(3): 2993-3003, 2014 Mar 07.
Artículo en Inglés | MEDLINE | ID: mdl-24609019

RESUMEN

New 1,2,4-triazole colorants were obtained, in high yields, by coupling 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole (1) with diazotized aniline derivatives 2, 4 and 6. The azo dyes prepared in this work may exist in three tautomeric forms. We found that the tautomerism is influenced mainly by the nature of substituent at the para position of the aniline coupling component. This tautomerisation was observed in the NMR spectra of the dyes. The dyes were characterized by IR, ¹H-NMR, ¹³C-NMR and MS spectroscopic techniques.


Asunto(s)
Compuestos Azo/química , Colorantes/química , Triazoles/química , Compuestos Azo/síntesis química , Técnicas de Química Sintética , Colorantes/síntesis química
7.
Molecules ; 17(5): 6011-9, 2012 May 18.
Artículo en Inglés | MEDLINE | ID: mdl-22609790

RESUMEN

A one-pot and clean synthesis of 2-arylbenzothiazoles via the ambient temperature reaction of 2-aminothiophenols and aromatic aldehydes without catalyst in glycerol as a green solvent has been reported.


Asunto(s)
Benzotiazoles/síntesis química , Glicerol/química , Benzotiazoles/química , Catálisis , Temperatura
8.
Beilstein J Org Chem ; 8: 18-24, 2012.
Artículo en Inglés | MEDLINE | ID: mdl-22423269

RESUMEN

The multicomponent reaction of 5-aminopyrazole derivatives with cyclic 1,3-dicarbonyl compounds and dimethylformamide dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded regioselectively 8,9-dihydropyrazolo[1,5-a]quinazolin-6(7H)-ones 6 rather than the corresponding dihydropyrazolo[5,1-b]quinazolin-8(5H)-ones 4.

9.
Molecules ; 13(11): 2908-14, 2008 Nov 24.
Artículo en Inglés | MEDLINE | ID: mdl-19037182

RESUMEN

A one-pot synthesis of 2-arylbenzothiazoles from the reaction of 2-aminothiophenol and aromatic aldehydes catalysed by cerium (IV) ammonium nitrate (CAN) is reported.


Asunto(s)
Benzotiazoles/síntesis química , Cerio/química , Nitratos/química , Catálisis , Cromatografía en Capa Delgada , Cromatografía de Gases y Espectrometría de Masas , Espectroscopía de Resonancia Magnética
10.
J Med Chem ; 55(9): 4169-77, 2012 May 10.
Artículo en Inglés | MEDLINE | ID: mdl-22509764

RESUMEN

In this paper we report the synthesis of some novel 1,2,4-triazolo[1,5-a]pyridine and azolotriazolopyridine ring systems. The products were screened for various types of activity like antibacterial, antifungal, and antioxidative activity. Compound 13 was found to pose an antioxidative activity. In addition, this compound was found to extend the life span of Caenorhabiditis elegans under standard laboratory conditions and reduces both heat and chemical induced oxidative stress in C. elegans in a dose-dependent manner. Furthermore, treatment of worms with compound 13 was found to significantly attenuate the formation of advanced glycation end products and malondialdehyde in a dose-dependent manner.


Asunto(s)
Antioxidantes/síntesis química , Caenorhabditis elegans/efectos de los fármacos , Estrés Oxidativo/efectos de los fármacos , Piridinas/síntesis química , Piridinas/farmacología , Triazoles/síntesis química , Triazoles/farmacología , Factores de Edad , Animales , Antioxidantes/química , Antioxidantes/farmacología , Caenorhabditis elegans/metabolismo , Productos Finales de Glicación Avanzada/metabolismo , Estimación de Kaplan-Meier , Espectroscopía de Resonancia Magnética , Malondialdehído/metabolismo , Espectrometría de Masas , Piridinas/química , Espectrofotometría Infrarroja , Triazoles/química
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