Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-<i>a</i>]pyrimidine from 5-Aminopyrazole Incorporated with <i>p</i>-Chloroaniline

Wedad Melad Al-Adiwish; Fatma Ali Shtewi; Munira Muftah Ashrif; Dalal Mohamed Ibrahim

doi:doi:10.11648/j.ajhc.20170306.15

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Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline

Wedad Melad Al-Adiwish, Fatma Ali Shtewi, Munira Muftah Ashrif, Dalal Mohamed Ibrahim

Published in American Journal of Heterocyclic Chemistry (Volume 3, Issue 6)

Received: 28 October 2017 Accepted: 8 December 2017 Published: 8 January 2018

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Abstract

5-Amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5-a]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene-S, S-and N, S-acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.

Published in	American Journal of Heterocyclic Chemistry (Volume 3, Issue 6)
DOI	10.11648/j.ajhc.20170306.15
Page(s)	86-94
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), 2024. Published by Science Publishing Group

Keywords

p-Chloroaniline, 5-aminopyrazole, Pyrazolo[1, 5-a]pyrimidines, Antibacterial Activity, Antifungal Activity, Cytotoxicity

References

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[19]	CCDC 1033261 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44 1223 336033, e-mail: deposit@ccdc.cam.ac.uk).
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Wedad Melad Al-Adiwish, Fatma Ali Shtewi, Munira Muftah Ashrif, Dalal Mohamed Ibrahim. (2018). Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. American Journal of Heterocyclic Chemistry, 3(6), 86-94. https://doi.org/10.11648/j.ajhc.20170306.15

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ACS Style

Wedad Melad Al-Adiwish; Fatma Ali Shtewi; Munira Muftah Ashrif; Dalal Mohamed Ibrahim. Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. Am. J. Heterocycl. Chem. 2018, 3(6), 86-94. doi: 10.11648/j.ajhc.20170306.15

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AMA Style

Wedad Melad Al-Adiwish, Fatma Ali Shtewi, Munira Muftah Ashrif, Dalal Mohamed Ibrahim. Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. Am J Heterocycl Chem. 2018;3(6):86-94. doi: 10.11648/j.ajhc.20170306.15

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@article{10.11648/j.ajhc.20170306.15,
  author = {Wedad Melad Al-Adiwish and Fatma Ali Shtewi and Munira Muftah Ashrif and Dalal Mohamed Ibrahim},
  title = {Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {6},
  pages = {86-94},
  doi = {10.11648/j.ajhc.20170306.15},
  url = {https://doi.org/10.11648/j.ajhc.20170306.15},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170306.15},
  abstract = {5-Amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5-a]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene-S, S-and N, S-acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.},
 year = {2018}
}

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TY  - JOUR
T1  - Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline
AU  - Wedad Melad Al-Adiwish
AU  - Fatma Ali Shtewi
AU  - Munira Muftah Ashrif
AU  - Dalal Mohamed Ibrahim
Y1  - 2018/01/08
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20170306.15
DO  - 10.11648/j.ajhc.20170306.15
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 86
EP  - 94
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20170306.15
AB  - 5-Amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5-a]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene-S, S-and N, S-acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.
VL  - 3
IS  - 6
ER  -

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Author Information

Wedad Melad Al-Adiwish

Chemistry Department, Faculty of Science, Azawia University, Az Zawiyah, Libya
Fatma Ali Shtewi

Chemistry Department, Faculty of Science, Azawia University, Az Zawiyah, Libya
Munira Muftah Ashrif

Chemistry Department, Faculty of Science, Azawia University, Az Zawiyah, Libya
Dalal Mohamed Ibrahim

Chemistry Department, Faculty of Science, Omar Al-mukhtar University, Al Bayda, Libya

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Plain Text BibTeX RIS

APA Style

Wedad Melad Al-Adiwish, Fatma Ali Shtewi, Munira Muftah Ashrif, Dalal Mohamed Ibrahim. (2018). Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. American Journal of Heterocyclic Chemistry, 3(6), 86-94. https://doi.org/10.11648/j.ajhc.20170306.15

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ACS Style

Wedad Melad Al-Adiwish; Fatma Ali Shtewi; Munira Muftah Ashrif; Dalal Mohamed Ibrahim. Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. Am. J. Heterocycl. Chem. 2018, 3(6), 86-94. doi: 10.11648/j.ajhc.20170306.15

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AMA Style

Wedad Melad Al-Adiwish, Fatma Ali Shtewi, Munira Muftah Ashrif, Dalal Mohamed Ibrahim. Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline. Am J Heterocycl Chem. 2018;3(6):86-94. doi: 10.11648/j.ajhc.20170306.15

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@article{10.11648/j.ajhc.20170306.15,
  author = {Wedad Melad Al-Adiwish and Fatma Ali Shtewi and Munira Muftah Ashrif and Dalal Mohamed Ibrahim},
  title = {Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {6},
  pages = {86-94},
  doi = {10.11648/j.ajhc.20170306.15},
  url = {https://doi.org/10.11648/j.ajhc.20170306.15},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170306.15},
  abstract = {5-Amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5-a]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene-S, S-and N, S-acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.},
 year = {2018}
}

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TY  - JOUR
T1  - Synthesis, Biological Activity and Cytotoxicity of New Fused Pyrazolo[1,5-a]pyrimidine from 5-Aminopyrazole Incorporated with p-Chloroaniline
AU  - Wedad Melad Al-Adiwish
AU  - Fatma Ali Shtewi
AU  - Munira Muftah Ashrif
AU  - Dalal Mohamed Ibrahim
Y1  - 2018/01/08
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20170306.15
DO  - 10.11648/j.ajhc.20170306.15
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 86
EP  - 94
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20170306.15
AB  - 5-Amino-3-(4-chlorophenylamino)-1H-pyrazole-4-carbonitrile 3 was prepared in high yield from the reaction of hydrazine hydrate with known 2-[(4-chlorophenylamino)(methylthio)methylene]malononitrile 2a (which was prepared from reaction of 2-[bis(methylthio)methylene]malononitrile 1 with p-Chloroaniline) under reflux in ethanol. The compound 3 was utilized as a key intermediate for the synthesis of pyrazolo[1, 5-a]pyrimidines 4a-b, 5a-c and 6 by reactions with some of ketene-S, S-and N, S-acetals. The antibacterial and antifungal activities, as well cytotoxicity against Breast cancer cells (MCF7) of some selected compounds are also reported.
VL  - 3
IS  - 6
ER  -

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