Design, synthesis, docking study and anticancer evaluation of new trimethoxyphenyl pyridine derivatives as tubulin inhibitors and apoptosis inducers

Hagras, Mohamed; Mandour, Asmaa A.; Mohamed, Esraa A.; Gobaara, Ibrahim M. M.; Mehany, Ahmed B. M.; Ismail, Nasser S. M.; Refaat, Hanan M.

doi:10.1039/d1ra07922k

Cited by 11 publications

(4 citation statements)

References 40 publications

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“…Furthermore, bioavailability radars provide a quick way to assess the drug‐likeness parameters of the tested compounds by looking at the optimal ranges for each property in the pink area, where the red line refers to the tested compounds as described previously (Ismail et al, 2023; Raslan et al, 2023). The bioavailability radars are generated based on six items (lipophilicity, polarity, saturation, size, solubility, and flexibility).…”

Section: Resultsmentioning

confidence: 99%

Explore new quinoxaline pharmacophore tethered sulfonamide fragments as in vitro α‐glucosidase, α‐amylase, and acetylcholinesterase inhibitors with ADMET and molecular modeling simulation

Ragab,

Salem,

Ammar

et al. 2024

Drug Development Research

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A new series of quinoxaline‐sulfonamide derivatives 3–12 were synthesized using fragment‐based drug design by reaction of quinoxaline sulfonyl chloride (QSC) with different amines and hydrazines. The quinoxaline‐sulfonamide derivatives were evaluated for antidiabetic and anti‐Alzheimer's potential against α‐glucosidase, α‐amylase, and acetylcholinesterase enzymes. These derivatives showed good to moderate potency against α‐amylase and α‐glucosidase with inhibitory percentages between 24.34 ± 0.01%–63.09 ± 0.02% and 28.95 ± 0.04%–75.36 ± 0.01%, respectively. Surprisingly, bis‐sulfonamide quinoxaline derivative 4 revealed the most potent activity with inhibitory percentages of 75.36 ± 0.01% and 63.09 ± 0.02% against α‐glucosidase and α‐amylase compared to acarbose (IP = 57.79 ± 0.01% and 67.33 ± 0.01%), respectively. Moreover, the quinoxaline derivative 3 exhibited potency as α‐glucosidase and α‐amylase inhibitory with a minute decline from compound 4 and acarbose with inhibitory percentages of 44.93 ± 0.01% and 38.95 ± 0.01%. Additionally, in vitro acetylcholinesterase inhibitory activity for designed derivatives exhibited weak to moderate activity. Still, sulfonamide‐quinoxaline derivative 3 emerged as the most active member with inhibitory percentage of 41.92 ± 0.02% compared with donepezil (IP = 67.27 ± 0.60%). The DFT calculations, docking simulation, target prediction, and ADMET analysis were performed and discussed in detail.

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Section: Resultsmentioning

confidence: 99%

Explore new quinoxaline pharmacophore tethered sulfonamide fragments as in vitro α‐glucosidase, α‐amylase, and acetylcholinesterase inhibitors with ADMET and molecular modeling simulation

Ragab,

Salem,

Ammar

et al. 2024

Drug Development Research

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“…To determine the GSBP seed phytocoumarins as anticancer candidates, a methodology based on the MTT dye was employed. [71] In which 5-flourouracil was used as a positive control, DMSO as a negative one, and eight cancerous populations were included as test species. These included MCF-7, MDA-MB-231, AR42 J, KYSE-30, SK-OV-3, HeLa, AMN3, and AB12.…”

Section: Anticancer Impactmentioning

confidence: 99%

Unveiling the Biomedical Applications of Novel Coumarins Isolated From Capsicum Annuum L. Seeds by a Multivariate Extraction Technique

Younes,

Mustafa

2024

Chemistry & Biodiversity

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For the first time, kinetic thermomagnetic extraction is a novel approach presented in this work. It required the application of four distinct variables: rotation speed (50, 75, and 100 rpm), magnetic field (0.8, 1.2, and 1.6 T), time interval (30, 60, and 90 min), and temperature (45, 55, and 65°C). Numerous phytochemical categories were detected in the 81 crude chloroform extracts of green sweet bell pepper seeds that were collected, according to phytochemical analysis. Nine extracts were discovered to be linked to the coumarin chemical class and to have the same two extraction parameters: a 90‐minute extraction duration and a 55°C extraction temperature. To enable their coumarin contents to be chemically separated and chromatographically purified, two of these extracts containing coumarin were chosen. Four new phytocoumarins have been identified and their molecular structures distinguished using FTIR spectra, 1H‐NMR, 13C‐NMR, and mass analysis. The results demonstrated that the extracted phytocoumarins have exceptional oxidative stress‐mitigating characteristics, ranging from 71.51 to 81.48%, when compared to a positive control. Furthermore, they showed excellent cytotoxicity against the test malignant populations (IC50 values of 46.76–81.45 μg/ml). The isolates need to be taken into account as dual COX‐2/5‐LOX antagonists because they also showed a selective anti‐inflammatory effect

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“…4-Nitro-substituted trimethoxy phenyl pyridine showed a signicant anticancer response against the HCT116, HEPG-2 and MCF7 cancer cell lines compared with hydroxy-, methoxy-, methyl-substituted and chloro trimethoxy phenyl pyridine. 17 Substituted pyrido pyrimidithione and substituted pyrazo pyridine showed interesting anticancer responses against the human hepatoma (Huh-7), lung cancer adenocarcinoma (A549) and Michigan cancer foundation 7 (MCF-7) cell lines with IC 50 values of 2.48 mm and 2.23 mm, respectively. 18 Antiproliferative screening of steroid-substituted pyridine moieties was performed against human tumor cell lines and some selected protein targets for breast cancer.…”

Section: Introductionmentioning

confidence: 99%

2-Chloro-3-cyano-4-nitrobenzyl pyridinium bromide as a potent anti-lung cancer molecule prepared using a single-step solvent-free method

Govindaraj,

Ganesan,

Elumalai

et al. 2024

RSC Adv.

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Design, synthesis, docking study and anticancer evaluation of new trimethoxyphenyl pyridine derivatives as tubulin inhibitors and apoptosis inducers

Abstract: Interaction of compounds VI (IC50 = 8.92 nM) (A) and Vj (IC50 = 10.75 nM) (B) with key amino acids of CBS.

Cited by 11 publications

References 40 publications

Explore new quinoxaline pharmacophore tethered sulfonamide fragments as in vitro α‐glucosidase, α‐amylase, and acetylcholinesterase inhibitors with ADMET and molecular modeling simulation

Explore new quinoxaline pharmacophore tethered sulfonamide fragments as in vitro α‐glucosidase, α‐amylase, and acetylcholinesterase inhibitors with ADMET and molecular modeling simulation

Unveiling the Biomedical Applications of Novel Coumarins Isolated From Capsicum Annuum L. Seeds by a Multivariate Extraction Technique

2-Chloro-3-cyano-4-nitrobenzyl pyridinium bromide as a potent anti-lung cancer molecule prepared using a single-step solvent-free method

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