Synthesis, cytotoxic activity and quantum chemical calculations of new 7-thioxopyrazolo[1,5-f]pyrimidin-2-one derivatives

Kökbudak, Zülbiye; Saraçoğlu, Murat; Akkoç, Senem; Çimen, Zeynep; Yılmazer, Mehmet; Kandemi̇rlı, Fatma

doi:10.1016/j.molstruc.2019.127261

Cited by 18 publications

(16 citation statements)

References 33 publications

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“…As outlined in Table , molecules 4k and 10 possess the highest values of ω (2.557 and 2.755, respectively), confirming their enhanced biological activity. I (ionization potential) is also, one of the essential chemical reactivity parameters; higher values meaning higher stability and vice versa . As displayed in Table , derivative 4k has the smallest value ( I = 0.201 eV) thus, 4k is the most active compound amongst all.…”

Section: Resultsmentioning

confidence: 98%

“…The obtained biological activity results demonstrate derivatives 4h , 4k , 10 , 12a , and 12b are the most active compounds that might be clarified from computational calculations. The relatively smaller value of gap energy (∆ E ) is mostly explained by higher activity and potentially higher performance in inhibition . The calculations revealed that the molecules 4h , 4k , 10 , 12a , and 12b provide smaller ∆ E (0.04643, 0.0148, 0.03654, 0.04335, 0.03582 eV, respectively), consequently possessing the best softness values that demonstrate the reactivity and inhibition of all these compounds.…”

Section: Resultsmentioning

confidence: 98%

“…solar cells . Moreover, the value of ω (global electrophilicity index) is the descriptive term of reactivity and is necessary to explain the molecules' toxicity . As outlined in Table , molecules 4k and 10 possess the highest values of ω (2.557 and 2.755, respectively), confirming their enhanced biological activity.…”

Section: Resultsmentioning

confidence: 99%

“…Pyridines are among the most important biochemical scaffolds with broader uses in the medicinal and pharmaceutical industries as well as intermediates in heterocyclic preparations . Among pyridine derivatives, dicyanopyridines act as ‘privileged skeleton’ owing to their prospective uses for therapy . These derivatives were recorded to serve as anti‐prion, human adenosine A2B receptor, antibacterial, anti‐cancer, and anti‐hepatitis B virus .…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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of main observation and conclusion A highly efficient, simple, and clean single-step sonosynthetic procedure has been sophisticated for assembling new series of mono-and bis-pyridine dicarbonitriles from ketones, HCl, and tetracyanoethylene. The presented protocol is applicable for the preparation of a broad range of uniquely substituted pyridine dicarbonitriles and seems to be superior in comparison with other previously reported methods. The antiproliferative impact of the newly synthesized derivatives was screened towards three representative cancer cell lines (MCF-7, A549, and HCT116). Most of the evaluated derivatives showed a moderate to excellent anti-proliferative activity towards the selected cell lines. Of these, compounds 4h, 4k, 10, 12a, and 12b showed both potent anticancer activity (IC50<10 μM) and lower cytotoxic effect (IC50 > 58 μM) on non-tumorigenic cells (MCF-10A and NCM460), suggesting their promising potential to be lead molecules for future antitumor drug discovery. The structure-activity relationships have been also discussed. Moreover, quantum chemical studies based on Density Functional Theory (DFT) of the synthesized compounds were investigated and found to be consistent with the in vitro inhibitory activities. Results and DiscussionPreparation of 6-chloro-[2,2'-bipyridine]-4,5-dicarbonitrile (4a) by treatment of tetracyanoethylene (1, TCNE, 1.0 mmol), and 2-acetyl pyridine (2a, 1.0 mmol) with HCl (3.0 mL) was chosen as the template reaction (Scheme 1) under silent (70 o C) and ultra-502 www.cjc.wiley-vch.de

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

See 2 more Smart Citations

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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“…Above results show that there is no solely sequence of reactivity, but dye molecules 7a and 5 appear to be more biologically reactive comparing to others. It is important to note that QCDs show just the tendency of biological reactivity, and this reactivity can be changed with respect to the structure of biological target [47,48].…”

Section: Calculated Quantum Chemical Descriptors For Investigated Dyesmentioning

confidence: 99%

Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity

et al. 2021

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Microwave‐induced one‐pot synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole hybrids as antiproliferative agents and density functional theory study

Chudasama,

Rajput,

Patel

et al. 2023

Archiv der Pharmazie

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Herein, we outline a highly efficient PEG‐4000‐mediated one‐pot three‐component reaction for the synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole derivatives (5a–r) at up to 96% yield as antiproliferative agents. This three‐component protocol offers the advantages of an environmentally benign reaction, excellent yield, quick response time, and operational simplicity triggered by the copper catalyst under microwave irradiation. All the synthesized compounds were tested for antiproliferative activity against six human solid tumor cell lines, that is, A549 and SW1573 (nonsmall cell lung), HBL100 and T‐47D (breast), HeLa (cervix), and WiDr (colon). Among them, six compounds, 5g–j, 5m, and 5p, demonstrated effective antiproliferative action with GI50 values under 10 μM. Furthermore, density functional theory (DFT) calculations were performed for all the synthesized molecules through geometry optimizations, frontier molecular orbital approach, and molecular electrostatic potential (MESP). The theoretical DFT calculation was performed using the DFT/B3LYP/6‐31+G (d,p) basis set. Moreover, the biological reactivity of all the representative synthesized molecules was compared with the theoretically calculated quantum chemical descriptors and MESP 3D plots. We also investigated the drug‐likeness characteristic and absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction. In general, our approach enables environmentally friendly access to 3‐imidazolyl indole clubbed 1,2,3‐triazole derivatives as prospective antiproliferative agents.

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Synthesis, cytotoxic activity and quantum chemical calculations of new 7-thioxopyrazolo[1,5-f]pyrimidin-2-one derivatives

Cited by 18 publications

References 33 publications

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity

Microwave‐induced one‐pot synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole hybrids as antiproliferative agents and density functional theory study

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