Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from  5-Aminopyrazole and Study Biological Activity and Cytotoxicity

Wedad M. Al-Adiwish; Maryam A. S. Abubakr; Naowara M. Alarafi

doi:doi:10.11648/j.cb.20170505.11

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Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from 5-Aminopyrazole and Study Biological Activity and Cytotoxicity

Wedad M. Al-Adiwish, Maryam A. S. Abubakr, Naowara M. Alarafi

Published in Cell Biology (Volume 5, Issue 5)

Received: 27 December 2016 Accepted: 9 January 2017 Published: 2 August 2017

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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.

Published in	Cell Biology (Volume 5, Issue 5)
DOI	10.11648/j.cb.20170505.11
Page(s)	45-52
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

Pyrazolo [5, 1-c] [1, 2, 4] triazines, p-Chloroaniline, 5-Aminopyrazole, Antibacterial Activity, Antifungal Activity, Cytotoxicity

References

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APA Style

Wedad M. Al-Adiwish, Maryam A. S. Abubakr, Naowara M. Alarafi. (2017). Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from 5-Aminopyrazole and Study Biological Activity and Cytotoxicity. Cell Biology, 5(5), 45-52. https://doi.org/10.11648/j.cb.20170505.11

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ACS Style

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 Biol. 2017, 5(5), 45-52. doi: 10.11648/j.cb.20170505.11

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AMA Style

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 Biol. 2017;5(5):45-52. doi: 10.11648/j.cb.20170505.11

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@article{10.11648/j.cb.20170505.11,
  author = {Wedad M. Al-Adiwish and Maryam A. S. Abubakr and Naowara M. Alarafi},
  title = {Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from  5-Aminopyrazole and Study Biological Activity and Cytotoxicity},
  journal = {Cell Biology},
  volume = {5},
  number = {5},
  pages = {45-52},
  doi = {10.11648/j.cb.20170505.11},
  url = {https://doi.org/10.11648/j.cb.20170505.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.cb.20170505.11},
  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.},
 year = {2017}
}

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TY  - JOUR
T1  - Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from  5-Aminopyrazole and Study Biological Activity and Cytotoxicity
AU  - Wedad M. Al-Adiwish
AU  - Maryam A. S. Abubakr
AU  - Naowara M. Alarafi
Y1  - 2017/08/02
PY  - 2017
N1  - https://doi.org/10.11648/j.cb.20170505.11
DO  - 10.11648/j.cb.20170505.11
T2  - Cell Biology
JF  - Cell Biology
JO  - Cell Biology
SP  - 45
EP  - 52
PB  - Science Publishing Group
SN  - 2330-0183
UR  - https://doi.org/10.11648/j.cb.20170505.11
AB  - 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.
VL  - 5
IS  - 5
ER  -

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Author Information

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

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APA Style

Wedad M. Al-Adiwish, Maryam A. S. Abubakr, Naowara M. Alarafi. (2017). Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from 5-Aminopyrazole and Study Biological Activity and Cytotoxicity. Cell Biology, 5(5), 45-52. https://doi.org/10.11648/j.cb.20170505.11

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ACS Style

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 Biol. 2017, 5(5), 45-52. doi: 10.11648/j.cb.20170505.11

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AMA Style

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 Biol. 2017;5(5):45-52. doi: 10.11648/j.cb.20170505.11

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@article{10.11648/j.cb.20170505.11,
  author = {Wedad M. Al-Adiwish and Maryam A. S. Abubakr and Naowara M. Alarafi},
  title = {Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from  5-Aminopyrazole and Study Biological Activity and Cytotoxicity},
  journal = {Cell Biology},
  volume = {5},
  number = {5},
  pages = {45-52},
  doi = {10.11648/j.cb.20170505.11},
  url = {https://doi.org/10.11648/j.cb.20170505.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.cb.20170505.11},
  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.},
 year = {2017}
}

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TY  - JOUR
T1  - Synthesis of New Pyrazolo [5, 1-c] [1, 2, 4] triazines from  5-Aminopyrazole and Study Biological Activity and Cytotoxicity
AU  - Wedad M. Al-Adiwish
AU  - Maryam A. S. Abubakr
AU  - Naowara M. Alarafi
Y1  - 2017/08/02
PY  - 2017
N1  - https://doi.org/10.11648/j.cb.20170505.11
DO  - 10.11648/j.cb.20170505.11
T2  - Cell Biology
JF  - Cell Biology
JO  - Cell Biology
SP  - 45
EP  - 52
PB  - Science Publishing Group
SN  - 2330-0183
UR  - https://doi.org/10.11648/j.cb.20170505.11
AB  - 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.
VL  - 5
IS  - 5
ER  -

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