Cargando…

Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives

5-Amino-N-aryl-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamides 4a–c were synthesized by the reaction of N-(aryl)-2-cyano-3-[(4-methoxyphenyl)amino]-3-(methylthio)acrylamides 3a–c with hydrazine hydrate in ethanol. The reaction of 5-amino-N-aryl-1H-pyrazoles 4a–c with acetylacetone 5 or 2-(4-me...

Descripción completa

Detalles Bibliográficos
Autores principales: Hassan, Ashraf S., Hafez, Taghrid S., Osman, Souad A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Austrian Journal of Pharmaceutical Sciences 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4727791/
https://www.ncbi.nlm.nih.gov/pubmed/26839799
http://dx.doi.org/10.3797/scipharm.1409-14
_version_ 1782412023642980352
author Hassan, Ashraf S.
Hafez, Taghrid S.
Osman, Souad A.
author_facet Hassan, Ashraf S.
Hafez, Taghrid S.
Osman, Souad A.
author_sort Hassan, Ashraf S.
collection PubMed
description 5-Amino-N-aryl-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamides 4a–c were synthesized by the reaction of N-(aryl)-2-cyano-3-[(4-methoxyphenyl)amino]-3-(methylthio)acrylamides 3a–c with hydrazine hydrate in ethanol. The reaction of 5-amino-N-aryl-1H-pyrazoles 4a–c with acetylacetone 5 or 2-(4-methoxybenzylidene)malononitrile 8 yielded the pyrazolo[1,5-a]pyrimidine derivatives 7a–c and 10a–c, respectively. The structures of the synthesized compounds were established based on elemental analysis and spectral data (IR, MS, (1)H-NMR, and (13)C-NMR). Representative examples of the new synthesized products were screened for their in vitro cytotoxic activity against Ehrlich Ascites Carcinoma (EAC) cells.
format Online
Article
Text
id pubmed-4727791
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher The Austrian Journal of Pharmaceutical Sciences
record_format MEDLINE/PubMed
spelling pubmed-47277912016-02-02 Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives Hassan, Ashraf S. Hafez, Taghrid S. Osman, Souad A. Sci Pharm Research Article 5-Amino-N-aryl-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamides 4a–c were synthesized by the reaction of N-(aryl)-2-cyano-3-[(4-methoxyphenyl)amino]-3-(methylthio)acrylamides 3a–c with hydrazine hydrate in ethanol. The reaction of 5-amino-N-aryl-1H-pyrazoles 4a–c with acetylacetone 5 or 2-(4-methoxybenzylidene)malononitrile 8 yielded the pyrazolo[1,5-a]pyrimidine derivatives 7a–c and 10a–c, respectively. The structures of the synthesized compounds were established based on elemental analysis and spectral data (IR, MS, (1)H-NMR, and (13)C-NMR). Representative examples of the new synthesized products were screened for their in vitro cytotoxic activity against Ehrlich Ascites Carcinoma (EAC) cells. The Austrian Journal of Pharmaceutical Sciences 2015 2014-10-24 /pmc/articles/PMC4727791/ /pubmed/26839799 http://dx.doi.org/10.3797/scipharm.1409-14 Text en Copyright: © Hassan et al. http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Hassan, Ashraf S.
Hafez, Taghrid S.
Osman, Souad A.
Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title_full Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title_fullStr Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title_full_unstemmed Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title_short Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives
title_sort synthesis, characterization, and cytotoxicity of some new 5-aminopyrazole and pyrazolo[1,5-a]pyrimidine derivatives
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4727791/
https://www.ncbi.nlm.nih.gov/pubmed/26839799
http://dx.doi.org/10.3797/scipharm.1409-14
work_keys_str_mv AT hassanashrafs synthesischaracterizationandcytotoxicityofsomenew5aminopyrazoleandpyrazolo15apyrimidinederivatives
AT hafeztaghrids synthesischaracterizationandcytotoxicityofsomenew5aminopyrazoleandpyrazolo15apyrimidinederivatives
AT osmansouada synthesischaracterizationandcytotoxicityofsomenew5aminopyrazoleandpyrazolo15apyrimidinederivatives