Design and synthesis of novel pyrazolo[3,4-d]pyrimidin-4-one bearing quinoline scaffold as potent dual PDE5 inhibitors and apoptotic inducers for cancer therapy

Ibrahim, Tarek S.; Hawwas, Mohamed M; Taher, Ehab S.; Alhakamy, Nabil A.; Alfaleh, Mohamed A.; Elagawany, Mohamed; Elgendy, Bahaa; Zayed, Gamal; Mohamed, Mamdouh F. A.; Abdel‐Samii, Zakaria K.; Elshaier, Yaseen A.M.M.

doi:10.1016/j.bioorg.2020.104352

Cited by 15 publications

(8 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…). 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm: 2.03 (s, 3H, CH 3 ), 2.24 (s, 3H, CH 3 ), 2.47 (s, 3H, CH 3 ), 4.85 (s, 1H, -CH-), 6.82 (s, 2H, -NH 2 ), 7.00-7.90 (m, 16H, Ar-H), 9.97 (s, 1H, NH). 13 H NMR (400 MHz, DMSO-d6) δ ppm: 2.03 (s, 3H, CH3), 2.24 (s, 3H, CH3), 4.85 (s, 1H, -CH-), 6.82 (s, 2H, -NH2), 7.00-7.90 (m, 16H, Ar-H), 9.97 (s, 1H, NH).…”

Section: Synthesis Of Target Molecule 1-(5-(1h-imidazol-1-yl)-3-methy...mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives

Patel,

Sharma,

Koshti

et al. 2024

ajc

View full text Add to dashboard Cite

In this work, a new series of imidazole-pyrazole-benzo[f]chromene hybrids were designed and synthesized by a base-catalyzed cyclo-condensation through a one-pot multicomponent reaction. All compounds were tested for in vitro antimicrobial and anticancer activities. Enzyme inhibitory activities of all compounds were carried out against FabH and EGFR. The majority of synthesized compounds displayed promising antimicrobial as well as anticancer activity against used strains and cancer cell lines respectively. The compounds were also tested for in vitro anticancer activities against two cancer cell lines A549 and Hep G2. Compound 7f (IC50 = 0.62 µM) against EGFR and (IC50 = 1.31 µM) against A549 kinase displayed the most potent inhibitory activity as compared to another member of the series. In the molecular modelling study, compound 7e was bound into the active pocket of EGFR with one pi-pi interaction and one hydrogen bond having minimum binding energy ∆Gb = −7.6894 kcal/mol. Moreover, FabH molecule 7d was found to be binding in the active pocket with a minimum binding energy of −8.9117 kcal/mol.

show abstract

Section: Synthesis Of Target Molecule 1-(5-(1h-imidazol-1-yl)-3-methy...mentioning

confidence: 99%

“…Studies on the discovery of cancer related drugs have made a remarkable progress but still the area needs a lot of research due to less effectiveness and selectivity [1]. It has also been reported that almost 80% of the deaths caused by cancer are related to lung cancer [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives

Patel,

Sharma,

Koshti

et al. 2024

ajc

View full text Add to dashboard Cite

show abstract

“…[61] F I G U R E 3 The structure of pyrazolo [3,4- (11-fold). [31] In 2020, Ibrahim et al [71] reported the synthesis of a series of pyrazolo [3,4-d]pyrimidin-4-ones carrying quinoline moiety. The NCI has chosen all the rationalized compounds for cytotoxic activity testing against 60 cell lines.…”

Section: Pyrazolo[34-d ]Pyrimidines As Egfr 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

View full text Add to dashboard Cite

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.

show abstract

“…They demonstrated that compound 78 induced an intrinsic apoptotic pathway that was evidenced by the lower expression levels of the anti-apoptotic Bcl-2 protein. (Ibrahim et al, 2020) Besides, pyrazolo [3,4-d]pyrimidine-6-amine 79 was reported and its mitochondrial permeability was elucidated along with, its inhibition activity against TNF Receptor Associated Protein 1 (TRAP1) that is responsible for abnormal mutations in different cell lines. As well, they proved the higher plasma and metabolic stability of compound 79 and its CYP acceptable inhibition.…”

Section: (Lamie Et Al 2021)mentioning

confidence: 99%

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

Salem¹,

Salem²,

Sabbagh

et al. 2022

Records of Pharmaceutical and Biomedical Sciences

View full text Add to dashboard Cite

Pyrazolo [3,4-d]pyrimidine is a bicyclic hetero organic nucleus that encompass a pyrazole ring fusion with a pyrimidine ring. Pyrazolo [3,4-d]pyrimidine nucleus could be synthesized using different synthetic procedures depending on either pyrazole or pyrimidine rings as starting synthones in addition to, different miscellaneous procedures. It was initially synthesized and evaluated as adenosine nucleoside analogues for cancer and viral therapy. Recently, numerous pyrazolo [3,4-d]pyrimidine compounds adopted anti-neoplastic activity via several mechanistic pathways. Also, designing drugs with pyrazolo [3,4-d]pyrimidine nucleus as pharmacophore encourage different biological activities such as anti-inflammatory, anti-microbial, antimycobacterial, anti-malarial, anti-gout and anti-diabetic. This bibliographic development presents an overview on works carried out on pyrazolo [3,4d]pyrimidine derivatives during the period 2017-2021.

show abstract

Design and synthesis of novel pyrazolo[3,4-d]pyrimidin-4-one bearing quinoline scaffold as potent dual PDE5 inhibitors and apoptotic inducers for cancer therapy

Cited by 15 publications

References 89 publications

Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives

Synthesis, Characterization, DFT Studies, Biological Investigation and Molecular Modelling of Novel 1-(5-(1H-imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)- 3-amino-2-cyano-N-phenyl-1H-benzo[f]chromene-5-carboxamide Derivatives

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

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

Contact Info

Product

Resources

About