(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

Cited by 15 publications

(5 citation statements)

References 29 publications

(31 reference statements)

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“…Pyrazole and pyrimidine rings are essential nitrogen containing heterocycles with interesting biological potential [24,58–65] . They are reported to show antimicrobial activity through inhibiting dihydropteroate synthase (DHPS) enzyme [14,24,66,67] …”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Bakr

Alolyyan

Elkanzi

et al. 2023

Chemistry & Biodiversity

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New series of pyrazoles 4a-c and pyrazolopyrimidines 5a -f had been constructed. The newly synthesized compounds were assessed for their antimicrobial activity towards E. coli and P. aeruginosa (gram -ve bacteria), B. subtilis and S. aureus (gram + ve bacteria) and A. flavus and C. albicans (representative of fungi). The pyrazolylpyrimidine-2,4-dione derivative 5b is the most active candidate against B. subtilis (MIC = 60 μg/mL) and P. aeruginosa (MIC = 45 μg/mL). Regarding antifungal potential, compound 5f was the most effective against A. flavus (MIC = 33 μg/mL). Similarly, compound 5c displayed strong antifungal activity towards C. Albicans (MIC = 36 μg/mL) in reference to amphotericin B (MIC = 60 μg/mL). Finally, the novel compounds had been docked inside dihydropteroate synthase (DHPS) to suggest the binding mode of these compounds.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Bakr

Alolyyan

Elkanzi

et al. 2023

Chemistry & Biodiversity

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“…These effects are primarily brought on by its suppression of EGFR, VEGFR-2 tyrosine kinases, and associated signaling pathways. [90] Bakr et al [91] synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1phenyl-1H-pyrazolo [3,4-d]pyrimidin-4-ylamino)phenyl]methanone (138) (Figure 25). The antiproliferative activity of this compound was tested on the breast (MCF-7), colon (HCT-116), and liver (HEPG-2) cancer cell lines.…”

Section: Pyrazolo[34-d ]Pyrimidines As Dual Egfr and Vegfr Inhibitorsmentioning

confidence: 99%

“…Bakr et al [ 91 ] synthesized (3,5‐dimethylpyrazol‐1‐yl)‐[4‐(1‐phenyl‐1 H ‐pyrazolo[3,4‐ d ]pyrimidin‐4‐ylamino)phenyl]methanone ( 138 ) (Figure 25). The antiproliferative activity of this compound was tested on the breast (MCF‐7), colon (HCT‐116), and liver (HEPG‐2) cancer cell lines.…”

Section: Pyrazolo[34‐d]pyrimidines As Dual Egfr and Vegfr Inhibitorsmentioning

confidence: 99%

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Kassab

2022

Archiv der Pharmazie

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The pyrazolo[3,4‐d]pyrimidine core has received a lot of interest from the medicinal chemistry community as a promising framework for drug design and discovery. It is an isostere of the adenine ring of adenosine triphosphate, which allows it to mimic kinase active site hinge region binding contacts. This scaffold has a wide pharmacological and biological value, one of which is as an anticancer agent. Many successful anticancer medicines have been designed and synthesized using pyrazolo[3,4‐d]pyrimidine as a key pharmacophore. The main synthetic routes of pyrazolo[3,4‐d]pyrimidines as well as their recent developments as promising anticancer agents acting as endothelial growth factor receptors and vascular endothelial growth factor receptor inhibitors, published in the time frame from 1999 to 2022, are summarized in this review to set the direction for the design and synthesis of novel pyrazolo[3,4‐d]pyrimidine derivatives for clinical deployment in cancer treatment.

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“…On the other hand, pyrimidine and thiazolidinone heterocycles attracted chemists’ attention due to their biological potential as well as their agrochemical effects. Both heterocycles exhibited potential as anticancer, − anti-inflammatory, − hypoglycemic, , antifungal, antioxidant, − antibacterial, ,, and insecticidal agents − and nicotinic acetylcholine inhibitors. − …”

Section: Introductionmentioning

confidence: 99%

Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora

et al. 2022

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An efficient and environmentally friendly method was established for designing novel 3-amino-1,4-dihydroquinoxaline-2-carbonitrile ( 1 ) via the reaction of bromomalononitrile and benzene-1,2-diamine under microwave irradiation in an excellent yield (93%). This targeted amino derivative was utilized for the construction of a series of Schiff bases ( 8 – 13 ). A new series of thiazolidinone derivatives ( 15 – 20 ) were synthesized in high yields (89–96%) via treatment of thioglycolic acid with Schiff bases ( 8 – 13 ) under microwave irradiation in high yields (89–96%). Moreover, new pyrimidine derivatives ( 26 – 30 and 35 – 38 ) were prepared by treatment of compound 1 with arylidenes ( 21 – 25 ) and/or alkylidenemalononitriles ( 31 – 34 ) using piperidine as a basic catalyst under microwave conditions. Based on elemental analyses and spectral data, the structures of the new assembled compounds were determined. The newly synthesized quinoxaline derivatives were screened and studied as an insecticidal agent against Aphis craccivora . The obtained results indicate that compound 16 is the most toxicological agent against nymphs of cowpea aphids ( Aphis craccivora ) compared to the other synthesized pyrimidine and thiazolidinone derivatives. The molecular docking study of the new quinoxaline derivatives registered that compound 16 had the highest binding score (−10.54 kcal/mol) and the thiazolidinone moiety formed hydrogen bonds with Trp143.

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

Cited by 15 publications

References 29 publications

Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora

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