Design, synthesis, anticancer evaluation and docking studies of novel 2-(1-isonicotinoyl-3-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-one derivatives as Aurora-A kinase inhibitors

Beniwal, Meenu; Jain, Neelam; Jain, Sandeep; Aggarwal, Navidha

doi:10.1186/s13065-022-00852-8

Cited by 8 publications

(5 citation statements)

References 37 publications

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“…These issues have been compounded by the widespread use of antibiotics and the infection caused by microorganisms resistant to drugs, 1,2 cancer is a deadly disease characterized by the uncontrolled growth of irritating cells. The medical uses of various anticancer drugs have been limited due to their non-selectivity, toxicity, side effects on healthy cells, and drug resistance [3][4][5][6] in addition to the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) that caused COVID-19, the worldwide pandemic that started by 2019, and spread quickly worldwide leading to high mortality and morbidity rates and no effective vaccines for governing the pandemic had been developed. 7,8 In this light, the development of more powerful endeavors, safer, more effective, and potent antimicrobial, anticancer and antiviral agents are urgently required to find the best treatment to fight these lethal diseases and to develop effective drugs with fewer adverse impacts.…”

Section: Introductionmentioning

confidence: 99%

A promising perspective through potential antimicrobial, anti‐cancer, and antiviral activity against SARS‐CoV‐2 of silver(I) complexes: Synthesis, characterization, density functional theory calculations, and in‐silico molecular docking studies

Elhusseiny,

Sherif,

Soliman

et al. 2024

Applied Organom Chemis

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This study tends to accomplish the sustainable development goal, which calls for all healthy lives. Antibiotic resistance, cancer, and severe acute respiratory syndrome coronavirus all showed high death rates in recent years. Our approach is to make better medications available to fight these feared health issues. In this context, three silver(I) complexes (1–3) based on the antibiotic gemifloxacin (HGMF) were synthesized and thoroughly examined using analytical, spectral, and thermal methods. The density functional theory suggested that complex 1 has a bent coordination environment while 2 and 3 have a distorted trigonal planar geometry. The optimal donor and acceptor centers were determined by the natural‐bond orbital analysis. Interaction of complexes with calf‐thymus DNA has been investigated and their binding constants were ordered as 3 > 2 > 1. The antimicrobial activity against 10 pathogenic microorganisms demonstrated that complex 3 exhibited superior activity compared with standard antibiotics. Testing against mammalian cell lines, liver carcinoma, breast carcinoma, and colon carcinoma revealed that complex 3 showed remarkable cell growth inhibition activity with IC50 values ranging from 3.0 to 9.3 μg/mL. Studies of Molecular docking against SARS‐CoV‐2 main protease Mpro (ID: 6 WTT) proved a powerful type of interaction at the active site. Complex 3 exhibits a potent inhibition effect with a total binding energy of −12.58 kcal/mol compared with the reference ligand inhibitor K36 suggesting its ability to block viral protease. This study presents promising bioactive candidates that have a practical impact on various medicinal fields.

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Section: Introductionmentioning

confidence: 99%

A promising perspective through potential antimicrobial, anti‐cancer, and antiviral activity against SARS‐CoV‐2 of silver(I) complexes: Synthesis, characterization, density functional theory calculations, and in‐silico molecular docking studies

Elhusseiny,

Sherif,

Soliman

et al. 2024

Applied Organom Chemis

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“…Therefore, 1,3,4-oxadiazole/thiadiazole derivatives have wide-spectrum pharmacological actions. There have been some reports suggesting that a 1,3,4-oxadiazole/thiadiazole moiety may be effective as an anticancer [19][20][21], antimicrobial [22,23], antioxidant [24,25], tyrosinase inhibitor [26], cathepsin K inhibitor [27], antitubercular [28,29], anti-diabetics [30], anti-inflammatory [31][32][33], anticonvulsant [34,35], antihypertensive activities [36], etc. These heterocyclic scaffolds are the main structural backbone of a wide range of drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anticancer, Antimicrobial and Antioxidant Potential of Novel 4-(Substituted phenyl-1,3,4-oxadiazol/thiadiazol-2-yl)-4-(4-substituted phenyl) Azetidin-2-One Derivatives

et al. 2023

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By exploiting the ample biological potential of 1,3,4-oxadiazole/thiadiazole ring, 4-substitutedphenyl-1,3,4-oxadiazol/Thiadiazol-2-yl)-4-(4-substitutedphenyl) azetidin-2-one derivatives were prepared. Various substituted azetidin-2-one derivatives have been identified as immunostimulating and antimicrobial, as well as their antioxidant activity. 2-amino 1,3,4 oxadiazole/thiadiazole conjugates were synthesized by mixing semi/thio carbazides and sodium acetate with water and stirring well, followed by adding aldehydes in methanol at room temperature. Acetate (glacial) was used as the catalyst to produce Schiff’s bases (intermediates) by treating substituted aldehydes with 2-amino 1,3,4 oxadiazole/thiadiazole(s). Using the mixture of triethylamine (dropwise) and chloroacetylchloride with vigorous stirring, 4-substitutedphenyl-1,3,4-oxadiazol/Thiadiazol-2-yl)-4-(4-substitutedphenyl) azetidin-2-one derivatives were prepared. The newly synthesized conjugates were evaluated for their anticancer potential using MCF-7 cell lines. Amoxicillin and fluconazole were used as reference drugs to determine their antimicrobial activity. Synthesized derivatives were evaluated for their antioxidant properties using 2-diphenyl-1-picrylhydrazyl (DPPH). In vitro cytotoxicity screening (MTTS assay) revealed that derivatives AZ-5, 9, 10, 14 and 19 demonstrated high efficacy with the percentage of inhibition at different concentration ranges (0.1 μM, 0.5 μM, 1 μM, 2 μM) of 89% to 94% μM as compared to doxorubicin as standard drug. The antimicrobial study indicated that compounds AZ-10, 19, and AZ-20 were found to have significant antimicrobial potential with MIC ranges of 3.34 µM to 3.71 µM in comparison to reference drugs having 4.29 µM to 5.10 µM. Based on antioxidant screening, most of the synthetic derivatives showed greater stability and effectiveness than the standard drug. According to the antioxidant screening, compounds AZ-5 and AZ-15 (IC50 = 45.02 μg/mL and 42.88 μg/mL, respectively) showed the greatest potency, as compared to ascorbic acid (IC50 = 78.63 μg/mL). Structure-activity relationship (SAR) studies of synthesized novel derivatives revealed that para-substituted halogen and nitro derivatives have remarkable potential against MCF-7 cancer cell lines and different microbial strains. Current evidence indicates that the synthesized derivatives may be promising candidates for use in the prevention and treatment of these infections. These synthesized compounds require further mechanism-based research to understand how they interact with the cells.

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“…Many different types of therapeutic approaches are being applied for the treatment of cancer. Several anticancer drugs are available around the world but most drugs are associated with large numbers of serious side effects, toxicity, and drug resistance [ 3 , 4 ]. Thus, it is crucial to develop novel anticancer molecules with great potential and fewer side effects.…”

Section: Introductionmentioning

confidence: 99%

2-Substituted-3-(5-Substituted-1,3,4-oxadiazol/thiadiazol-2-yl) Thiazolidin-4-one Derivatives: Synthesis, Anticancer, Antimicrobial, and Antioxidant Potential

et al. 2023

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In this innovative research, a novel series of thiazolidin-4-one analogues having a 1,3,4-oxadiazole/thiadiazole moiety were derived and the structures of all the newly obtained molecules were established using different physicochemical and analytical means (1H-NMR, FTIR, mass spectra, and elemental analyses). The synthesized molecules were then investigated for their antiproliferative, antimicrobial, and antioxidant potential. The cytotoxicity screening studies revealed that analogues D-1, D-6, D-15, and D-16 possessed comparable efficacy, within the IC50 range (1 to 7 μM), when taking doxorubicin as a reference drug (IC50 = 0.5 μM). The antimicrobial activity was assessed using different Gram-(+) and Gram-(−) bacterial and fungal strains and the results revealed that molecules D-2, D-4, D-6, D-19, and D-20 possessed potent activity against selective strains of microbes with MIC ranges of 3.58 to 8.74 µM. The antioxidant evaluation was performed using the DPPH assay and the screening results revealed that analogue D-16 was the most potent derivative (IC50 = 22.3 µM) when compared with the positive control, ascorbic acid (IC50 = 111.6 µM). Structure–activity relationship (SAR) studies of the synthesized novel derivatives revealed that para-substituted halogen and hydroxy derivatives have remarkable potential against the MCF-7 cancer cell line and antioxidant potential. Similarly, electron-withdrawing groups (Cl/NO2) and -donating groups at the para position possess moderate to promising antimicrobial potential.

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Design, synthesis, anticancer evaluation and docking studies of novel 2-(1-isonicotinoyl-3-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-one derivatives as Aurora-A kinase inhibitors

Cited by 8 publications

References 37 publications

A promising perspective through potential antimicrobial, anti‐cancer, and antiviral activity against SARS‐CoV‐2 of silver(I) complexes: Synthesis, characterization, density functional theory calculations, and in‐silico molecular docking studies

A promising perspective through potential antimicrobial, anti‐cancer, and antiviral activity against SARS‐CoV‐2 of silver(I) complexes: Synthesis, characterization, density functional theory calculations, and in‐silico molecular docking studies

Synthesis, Anticancer, Antimicrobial and Antioxidant Potential of Novel 4-(Substituted phenyl-1,3,4-oxadiazol/thiadiazol-2-yl)-4-(4-substituted phenyl) Azetidin-2-One Derivatives

2-Substituted-3-(5-Substituted-1,3,4-oxadiazol/thiadiazol-2-yl) Thiazolidin-4-one Derivatives: Synthesis, Anticancer, Antimicrobial, and Antioxidant Potential

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