(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone

Bakr, Rania B.; Mehany, Ahmed B. M.

doi:10.3390/M915

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(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone

Rania B. Bakr

^1,2,* and

Ahmed B. M. Mehany

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni Suef University, Beni Suef 62514, Egypt

Department of Pharmaceutical Chemistry, College of Pharmacy, Al Jouf University, Sakaka, Al Jouf 2014, Saudi Arabia

Department of Zoology, Faculty of Science, Al-Azhar University, Cairo 11884, Egypt

Author to whom correspondence should be addressed.

Academic Editor: Norbert Haider

Molbank 2016, 2016(4), M915; https://doi.org/10.3390/M915

Received: 28 September 2016 / Revised: 29 October 2016 / Accepted: 8 November 2016 / Published: 10 November 2016

(This article belongs to the Section Organic Synthesis)

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Abstract

In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast (MCF-7), colon (HCT-116), and liver (HEPG-2) cancer cell lines. The tested compound exhibited cytotoxic activity with IC₅₀ = 5.00–32.52 μM. Moreover, inhibitory activity of this compound was evaluated against the epidermal growth factor receptor (EGFR), the fibroblast growth factor receptor (FGFR), the insulin receptor (IR), and the vascular endothelial growth factor receptor (VEGFR). This target compound showed potent inhibitory activity, especially against FGFR with IC₅₀ = 5.18 μM. View Full-Text

Keywords: pyrazole; pyrazolo[3,4-d]pyrimidine; anticancer; protein kinases

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Supplementary File 1:
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Supplementary File 2:
Supplementary 3D structure (MOL, 3 KiB) Display in JSmol Viewer
3D structure generated by CORINA Classic by MN-AM.
Supplementary File 3:
Supplementary (INCHI, 950 B)
Supplementary File 4:
Supplementary (MOL, 3 KiB) Display in JSmol Viewer

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Bakr, R.B.; Mehany, A.B.M. (3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone. Molbank 2016, 2016, M915. https://doi.org/10.3390/M915

AMA Style

Bakr RB, Mehany ABM. (3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone. Molbank. 2016; 2016(4):M915. https://doi.org/10.3390/M915

Chicago/Turabian Style

Bakr, Rania B., and Ahmed B.M. Mehany. 2016. "(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone" Molbank 2016, no. 4: M915. https://doi.org/10.3390/M915

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(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone

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