Synthesis of novel pyrazolo[3,4-d]pyrimidine derivatives as potential anti-breast cancer agents

Hamid, Mohammed K. Abd El; Mihovilovic, Marko D.; El‐Nassan, Hala B.

doi:10.1016/j.ejmech.2012.09.031

Cited by 48 publications

(11 citation statements)

References 20 publications

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“…The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, cardiovascular system, cancer and inflammation. [19][20][21] In addition, several 1,3-thiazole scaffolds have been reported as potent anticancer agents. [22][23][24] The synthesis of some new pyrazole-based 1,3-thiazoles as anticancer agents was reported.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

Kamel

2015

ACSi

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The reaction of 1 with phenylisothiocyanate followed by treatment with the α-halocarbonyl compounds 24a-c afforded the thiazole derivatives 25a-c. The synthesized products were evaluated for their cytotoxicity against cancer and normal cell lines. Most compounds showed significant anticancer activity without affecting the normal fibroblast cells. The toxicity of the most pontent cytotoxic compounds was measured using Brine-Shrimp Lethality Assay.

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Section: Introductionmentioning

confidence: 99%

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

Kamel

2015

ACSi

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“…In addition, the literature survey revealed that the pyrazole moiety represents an important pharmacophore in several anticancer active cancer agents. Compound 2 was the most active compound in this search with an IC50 equal to 7.5 nM [21]. In addition, the literature survey revealed that the pyrazole moiety represents an important pharmacophore in several anticancer active agents [22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 89%

“…El Hamid et al synthesized and evaluated a new set of 1-aryl-4-benzylidenehydrazinyl-3methylsulphanyl-pyrazolo [3,4-d]pyrimidines as anti-breast cancer agents. Compound 2 was the most active compound in this search with an IC 50 equal to 7.5 nM [21]. In addition, the literature survey revealed that the pyrazole moiety represents an important pharmacophore in several anticancer active cancer agents.…”

Section: Introductionmentioning

confidence: 90%

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

Bakr

Mehany

2016

Molbank

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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 IC 50 = 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 IC 50 = 5.18 µM.

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“…Screening the literature declared the antitumor activity of many 4-aralkylamino/anilino-pyrazolo [3,4-d]pyrimidines (9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Some of these derivatives exerted their antitumor activity via inhibition of EGFR tyrosine kinase as demonstrated by compounds I-III (19)(20)(21). Moreover, many derivatives with potent antitumor activity were found to possess 4-(un)substitutedphenylpiperidinyl IV (22) and 4-(un)substitutedphenyl-piperazinyl moieties V (23) at position 4 of the pyrazolopyrimidine nucleus (Chart 1).…”

mentioning

confidence: 99%

4‐Substituted‐1‐phenyl‐1H‐pyrazolo[3,4‐d]pyrimidine Derivatives: Design, Synthesis, Antitumor and EGFR Tyrosine Kinase Inhibitory Activity

et al. 2014

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Four series of some 4-substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives 5a-f, 6a-f, 8a-f, and 9a-f were designed to be screened for their antitumor activity. All compounds were evaluated against breast (MCF-7) and lung (A-549) cell lines. Six compounds 5a, 5b, 6b, 6e, 9e, and 9f displaying activity against both cell lines were further estimated for their EGFR-TK inhibitory activity where they revealed 41-91% inhibition and compound 6b elicited the highest activity (91%). A docking study of these compounds into the ATP-binding site of EGFR-TK demonstrated their binding mode where H-bonding interaction with Met793 through N(1) of pyrimidine or N(2) of pyrazole was observed.

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Synthesis of novel pyrazolo[3,4-d]pyrimidine derivatives as potential anti-breast cancer agents

Cited by 48 publications

References 20 publications

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

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

4‐Substituted‐1‐phenyl‐1H‐pyrazolo[3,4‐d]pyrimidine Derivatives: Design, Synthesis, Antitumor and EGFR Tyrosine Kinase Inhibitory Activity

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