Cytotoxic activity and density functional theory studies of some 1,3-diphenylpyrazolyltetrahydropyrimidine derivatives

Ramadan, Sayed K.; Halim, Karema N. M.; Rizk, Sameh A.; El‐Hashash, Maher A.

doi:10.1007/s13738-020-01880-8

Cited by 26 publications

(7 citation statements)

References 37 publications

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“…Pyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities [2,3], and several drugs currently on the market, have the pyrazole ring as the key structural motif [4]. Some pyrazole derivatives have been demonstrated to be cytotoxic on several human cell lines [5][6][7][8], and, at this time, several drugs that have pyrazoles in their structure have been approved for the treatment of different types of cancer (see Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

et al. 2021

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Background Pyrazoles have attracted particular attention due to the diverse biological activities associated with this heterocyclic system, and some have been shown to be cytotoxic to several human cell lines. Several drugs currently on the market have this heterocycle as the key structural motif, and some have been approved for the treatment of different types of cancer. Results 4,4ʹ-(Arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a–q were synthetized by a three components reaction of 3-methyl-1-phenyl-5-pyrazolone (1) with various benzaldehydes 2 catalyzed by sodium acetate at room temperature. The structures of all synthesized compounds were characterized by physicochemical properties and spectral means (IR and NMR) and were evaluated for their radical scavenging activity by DPPH assay and tested in vitro on colorectal RKO carcinoma cells in order to determine their cytotoxic properties. All 4,4ʹ-(arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a–q were synthetized in high to excellent yield, and pure products were isolated by simple filtration. All compounds have good radical scavenging activity, and half of them are more active than ascorbic acid used as standard. Conclusion Several derivatives proved to be cytotoxic in the RKO cell line. In particular, compound 3i proved to be a very potent scavenger with an IC50 of 6.2 ± 0.6 µM and exhibited an IC50 of 9.9 ± 1.1 μM against RKO cell. Autophagy proteins were activated as a survival mechanism, whereas the predominant pathway of death was p53-mediated apoptosis.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

et al. 2021

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“…The IR spectrum of 2 exhibited the absorption bands for NH and C O groups. Further evidence for the assigned structure 2 is acquired from its 1 H NMR spectrum that provided two exchangeable broad singlet signals for two NH protons, as well as a singlet signal for methine proton of pyrimidine ring and two singlet signals for the protons of two methyl groups (cf. Section 4).…”

Section: Chemistrymentioning

confidence: 99%

Straightforward synthesis, antiproliferative screening, and density functional theory study of some pyrazolylpyrimidine derivatives

Halim

Rizk

El‐Hashash

et al. 2020

Journal of Heterocyclic Chem

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Tetrahydropyrimidinone derivative was synthesized through one‐pot three components condensation of 1,3‐diphenylpyrazole‐4‐carbaldehyde with pentan‐2,4‐dione and urea under Biginelli reaction conditions. The corresponding chloro‐ and hydrazino derivatives were synthesized and utilized for the construction of some valuable N‐heterocycles encompassing both pyrazole and pyrimidine cores, such as triazolopyrimidine, tetrazolopyrimidine, pyrazole, and pyrazolone derivatives through condensation with nitrogen nucleophiles and carbon electrophiles. The antiproliferative activity evaluation of the synthesized compounds against four human carcinoma cell lines namely, liver carcinoma (HepG2), breast adenocarcinoma (MCF7), prostate cancer (PC3), and colon cancer (HCT‐116) cell lines revealed that some of them provided significant potency, as well as the density‐functional theory (DFT) was studied. The permeability of various hydrophilic and hydrophobic synthesized compounds across both normal and cancer cells is confirmed via DFT simulation in which the much higher permeability through aquaporin channels revealed the selective cytotoxicity toward cancer cells.

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“…Heterocyclic compounds, especially nitrogen heterocycles, play an important role in the process of drug development and drug analysis (approximately two-thirds of the medicines available on the market include a heterocyclic skeleton). 1–13 Accordingly, furanones are found to be easily converted to a variety of heterocyclic skeletons of biological importance. 14–20 A broad range of pharmacological activities including insecticidal, antiviral, anticancer, antimicrobial, antimalarial, anti-inflammatory, and analgesic properties have been documented in quinoline (benzo[ b ]pyridine) derivatives (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3H)-one against Culex pipiens L. larvae

et al. 2022

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Cytotoxic activity and density functional theory studies of some 1,3-diphenylpyrazolyltetrahydropyrimidine derivatives

Cited by 26 publications

References 37 publications

Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

Straightforward synthesis, antiproliferative screening, and density functional theory study of some pyrazolylpyrimidine derivatives

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3H)-one against Culex pipiens L. larvae

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