Green synthesis and 3D pharmacophore study of pyrimidine and glucoside derivatives with in vitro potential anticancer and antioxidant activities

Salem, Mohammed A.-M.; Behalo, Mohamed S.; Elrazaz, Eman Z.

doi:10.1007/s00044-019-02367-9

Cited by 12 publications

(8 citation statements)

References 37 publications

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“…In continuation of our program aiming to synthesize polyfunctional substituted heterocyclic compounds of potential biological activity, [ 3,4,8,17,18,23–29 ] the synthesis of poly‐functionalized 7‐amino‐5‐(4‐methoxyphenyl)‐2,4‐dioxo‐1,2,3,4‐tetrahydropyrido[2,3‐ d ]pyrimidine‐6‐carbonitrile ( 1a ) and 2‐amino‐4‐(4‐methoxyphenyl)‐5‐oxo‐5 H ‐dipyrido[1,2‐a:3′,2′‐ e ]pyrimidine‐3‐carbonitrile ( 1b ) was achieved via one‐pot multicomponent reactions of the barbituric acid and/or 3 H ‐pyrido [1,2‐ a ]pyrimidine‐2,4‐dione, [ 26 ] anisaldehyde, ammonium acetate and malononitrile or three‐component reactions of barbituric acid and/or 3 H ‐pyrido[1,2‐ a ]pyrimidine‐2,4‐dione, arylidine of malononitrile and ammonium acetate, under fusion at 150°C (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…[ 11 ] It also worthy to mention that, 2‐amino‐3‐cyanopyridines in particular are known as‐IKK‐β‐inhibitors. [ 12 ] Furthermore, they have been identified to possess multiple biological activities such as anti‐microbial, anti‐bacterial, anti‐fungal, anti‐tumor, [ 8,13–18 ] anti‐viral, [ 19 ] anti‐inflammatory, [ 20 ] over and above anti‐hypertensive properties. [ 21 ] Besides, they have been utilized as important‐and useful intermediates and scaffolds in construction of a variety of heterocyclic products.…”

Section: Introductionmentioning

confidence: 99%

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3D‐pharmacophore study molecular docking and synthesis of pyrido[2,3‐d]pyrimidine‐4(1H) dione derivatives with in vitro potential anticancer and antioxidant activities

Gouda

Salem

Mahmoud

2020

Journal of Heterocyclic Chem

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Some poly functionalized heterocyclic‐compounds containing pyridine‐moieties were readily assembled by combining differently functionalized pyridopyrimidine‐6‐carbonitrile derivatives 1a,b with different electrophilic and nucleophilic reagents via short synthetic routes. The structures of the prepared derivatives were ascertained from their‐spectral‐and elemental analyses. Some of the synthesized compounds were tested as plausible antitumor agents. Most of those tested compounds likes 7, 9, 10, 11a showed cytotoxic potencies against different tumor cell lines. In addition, the assessments for their antioxidant activities have also been done and compound 9 exhibited the highest antioxidant activity while compounds 7 and 10 showed moderate activities. Finally, molecular docking studies were carried out which favorably indicated a high support for the experimental‐results.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

3D‐pharmacophore study molecular docking and synthesis of pyrido[2,3‐d]pyrimidine‐4(1H) dione derivatives with in vitro potential anticancer and antioxidant activities

Gouda

Salem

Mahmoud

2020

Journal of Heterocyclic Chem

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“…The top pharmacophore hypothesis generated was developed with a total cost value of 104.77, null cost = 226.1, and fixed cost = 59.75. Further evaluation of the generated pharmacophore models was based on the correlation coefficient, [ 26 ] which was found to be 0.869, indicating the capability of the pharmacophore model to predict the activity of the training set compounds. The predicted activities through the pharmacophore model are represented in Table 6 as well as their fit values.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new arylazopyrazoles as apoptosis inducers: Candidates to inhibit proliferation of MCF‐7 cells

Ismail

Soliman

Sabour

et al. 2020

Archiv der Pharmazie

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New 4‐arylazo‐3,5‐diamino‐1H‐pyrazole derivatives substituted in the 4‐aryl ring with the acetyl moiety were designed and synthesized. The antiproliferative activity of the novel arylazopyrazoles was examined against the MCF‐7 cell line. Among all target compounds, 8b (IC50 3.0 µM) and 8f (IC50 4.0 µM) displayed higher cytotoxicity as compared with the reference standard imatinib (IC50 7.0 µM). Further studies to explore the mechanism of action were performed on the most active hit of our library, 8b, via anti‐CDK2 kinase activity. It demonstrated good inhibitory effects for CDK2 (IC50 0.24 µM) with 62.5% inhibition, compared with imatinib. The cell cycle analysis in the MCF‐7 cell line revealed apoptosis induction by 8b and cell cycle arrest at the S phase. Docking in the CDK2 active site and pharmacophore modeling confirmed the affinity of 8b to the CDK2 active site. Absorption, distribution, metabolism, and excretion studies revealed that our target compounds are orally bioavailable, with no permeation through the blood–brain barrier.

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“…In this study, quantum chemical calculations of previously synthesized pyrimidine compounds 30 were studied. The electronic properties of the molecules, corrosion prevention parameters and electrostatic potential maps (MEP) properties were theoretically calculated on the DFT-B3LYP / 6-31 G (d, p) base set.…”

Section: Discussionmentioning

confidence: 99%

Determination of electronic characteristics of tetrahydro pyrimidine derivatives and investigation of usability as anti-corrosion

Akbaş

Okay

Ergan

et al. 2021

International Journal of Chemistry and Technology

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Corrosion of metallic structures is a serious problem in most industries worldwide. This problem can be controlled by the addition of chemicals capable of adsorption onto the metal surface. The metal can be isolated from the corrosive environment. These chemicals are often selected from groups containing free electron pairs and / or π electrons, which are rich in functional groups. In this study, electronic structures Highest Molecular Orbital (HOMO), Lowest Occupied Molecular Orbital (LUMO), MEP, energy gap (ΔE), ionization potential (I), electron affinity (A), chemical structure of pyrimidine derivative compounds containing unpaired electron pairs, π electrons, functional groups such as N, O and S hardness and softness (S), general electrophilic index (ω), transmitted electron fraction index (ΔN) and recovery (backEbackdonation) properties of quantum chemical calculation methods to investigate the properties of the selected compounds in this direction and adsorbed to the surface with the quantum chemical calculation methods. The aim of this study is to determine the efficiency of synthesized compounds as anticorrosion materials and to provide new gains to the industry in this sense.

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Green synthesis and 3D pharmacophore study of pyrimidine and glucoside derivatives with in vitro potential anticancer and antioxidant activities

Cited by 12 publications

References 37 publications

3D‐pharmacophore study molecular docking and synthesis of pyrido[2,3‐d]pyrimidine‐4(1H) dione derivatives with in vitro potential anticancer and antioxidant activities

3D‐pharmacophore study molecular docking and synthesis of pyrido[2,3‐d]pyrimidine‐4(1H) dione derivatives with in vitro potential anticancer and antioxidant activities

Synthesis of new arylazopyrazoles as apoptosis inducers: Candidates to inhibit proliferation of MCF‐7 cells

Determination of electronic characteristics of tetrahydro pyrimidine derivatives and investigation of usability as anti-corrosion

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