Volume 5, Issue 5, September 2017, Page: 45-52
Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from 5-Aminopyrazole and Study Biological Activity and Cytotoxicity
Wedad M. Al-Adiwish, Chemistry Department, Faculty of Science, Azawia University, Az Zawiyah, Libya
Maryam A. S. Abubakr, Department of Botany, Faculty of Science, Azawia University, Az Zawiyah, Libya
Naowara M. Alarafi, Chemistry Department, Faculty of Science, Benghazi University, Benghazi, Libya
Received: Dec. 27, 2016;       Accepted: Jan. 9, 2017;       Published: Aug. 2, 2017
DOI: 10.11648/j.cb.20170505.11      View  1857      Downloads  91
Abstract
Treatment of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline afforded 2-[(4-chlorophenylamino) (methylthio) methylene] malononitrile 2a, of which upon reaction with hydrazine hydrate yielded 5-amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3. This compound was utilized as a key intermediate for the synthesis of pyrazolo [5, 1-c] [1, 2, 4] triazines by diazotization of 3 with nitrous acid at low temperature afforded 3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile-5-diazonium chloride 3', in which coupling with active methylene of acetylacetone and malononitrile in the presence of pyridine gave the hydrazone derivatives, which cyclized directly upon addition of acetic acid to produce respective pyrazolo [5, 1-c] [1, 2, 4] triazine derivatives 7 and 8. Finally, treatment of 3 with acetic anhydride gave the acetyl amide derivative 9. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.
Keywords
Pyrazolo [5, 1-c] [1, 2, 4] triazines, p-Chloroaniline, 5-Aminopyrazole, Antibacterial Activity, Antifungal Activity, Cytotoxicity
To cite this article
Wedad M. Al-Adiwish, Maryam A. S. Abubakr, Naowara M. Alarafi, Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from 5-Aminopyrazole and Study Biological Activity and Cytotoxicity, Cell Biology. Vol. 5, No. 5, 2017, pp. 45-52. doi: 10.11648/j.cb.20170505.11
Copyright
Copyright © 2017 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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