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Molecules 2014, 19(3), 3297-3309; doi:10.3390/molecules19033297
Article

Synthesis and Anticancer Activity of Some New Pyrazolo[3,4-d]pyrimidin-4-one Derivatives

1
,
1
,
1
,
2
 and
1,*
1 Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt 2 Cell Biology and Histology Division, Zoology Department, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt
* Author to whom correspondence should be addressed.
Received: 31 December 2013 / Revised: 27 February 2014 / Accepted: 5 March 2014 / Published: 18 March 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

3,6-Dimethyl-1-phenyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one (3) was prepared by hydrolysis of ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) to afford the corresponding carboxylic acid 2, which was reacted with acetic anhydride to give 3. The pyrazolo[3,4-d][1,3]oxazin-4-one 3 was reacted with hydroxylamine hydrochloride, urea, thiourea, thiosemicarbazide, phenylhydrazine and aromatic amines to afford the corresponding pyrazolo[3,4-d]pyrimidin-4-ones 4, 5a,b, 6, 7, 8ae, respectively. Condensation of pyrazoloxazine derivative 3 with 99% hydrazine hydrate afforded the 5-aminopyrazolo[3,4-d] pyrimidine derivative 9. Coupling of 9 with aromatic aldehydes yielded a series of 3,6-dimethyl-5-(4-substitutedbenzylideneamino)-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin- 4-ones 10ae. The new compounds were tested for their antitumor activity on the MCF-7 human breast adenocarcinoma cell line. Almost all the tested compounds revealed antitumor activity, especially 3,6-dimethyl-5-(4-nitrobenzylideneamino)-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one (10e) which displayed the most potent inhibitory activity with a half maximal inhibitory concentration (IC50) of 11 µM.
Keywords: pyrazolo[3,4-d]pyrimidin-4-one; anticancer activity; MCF7 pyrazolo[3,4-d]pyrimidin-4-one; anticancer activity; MCF7
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Abdellatif, K.R.A.; Abdelall, E.K.A.; Abdelgawad, M.A.; Ahmed, R.R.; Bakr, R.B. Synthesis and Anticancer Activity of Some New Pyrazolo[3,4-d]pyrimidin-4-one Derivatives. Molecules 2014, 19, 3297-3309.

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