Synthesis of some 5‐arylidene‐2‐(4‐acetamidophenylimino)‐thiazolidin‐4‐one derivatives and exploring their breast anticancer activity

Abumelha, Hana M.; Saeed, Ali

doi:10.1002/jhet.3906

Cited by 18 publications

(14 citation statements)

References 31 publications

(48 reference statements)

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“…We completed the reaction mix by adding 19 μl of nuclease‐free water. All reactions were performed for 35 cycles using the following temperature profiles: “95°C for 5 min (initial denaturation); 95°C for 15 min (Denaturation), 55°C for 30 min (Annealing), and 72°C for 30 min (Extension)” (Abumelha & Saeed, 2020; Nirwan et al, 2019). Then, the C t values were collected to calculate the relative genes’ expression in all samples by normalization to the β‐actin housekeeping gene (Nafie, Arafa, et al, 2020; Nafie et al, 2021).…”

Section: Methodsmentioning

confidence: 99%

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

et al. 2021

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Quinoline-based thiazolidinone heterocycles exhibited potent activity in the field of cancer therapy. Hence, ten quinoline-based thiazolidinone derivatives were evaluated for their anticancer activity through cytotoxic activity, epidermal growth factor receptor (EGFR) inhibition pathway, apoptosis investigation through flow cytometric analyses, RT-PCR gene expression, in vivo solid-Ehrlich carcinoma model, and finally in silico approach for highlighting the interaction pose. Results revealed that compound 7 exhibited cytotoxic activity against HCT-116 cells with an IC 50 value of 7.43 µM compared to 5-FU (IC 50 = 11.36 µM) with moderate cytotoxic activity against the FHC (IC 50 = 35.27 µM), and it exhibited remarkable inhibition activity of EGFR with IC 50 value of 96.43 nM compared to Erlotinib (IC 50 = 78.65 nM). Moreover, it significantly stimulated apoptotic colon cancer cell death with 171.58-fold arresting cell cycle at G2 and S-phases.Additionally, it ameliorated both biochemical and histochemical structures near normal with tumor inhibition ratio of 52.92% compared to 5-FU of 57.16%, with immunohistochemical examinations of EGFR inhibition in the treated group compared to control. Finally, molecular docking study highlighted its good binding affinity through good interactive binding pose inside the EGFR protein. In conclusion, the potent EGFR inhibitory activity of compound 7 was investigated using three integrated approaches in vitro, in vivo, and in silico, so it worth be validated and developed as a chemotherapeutic anticancer agent.

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Section: Methodsmentioning

confidence: 99%

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

et al. 2021

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“…The thioureas so obtained were cyclized by refluxing with ethyl bromoacetate in the presence of sodium acetate to give the title compounds 160 in good yields. Compound 160a revealed good anticancer activity as determined by the MTT assay with 35.82% inhibition in HeLa cells at a dose of 10 μM while no toxicity was shown against NIH3T3 mouse fibroblast cells at the same dose with a 98.19% survival rate [39] thiazolidinone scaffold by a substituted-benzylidene moiety enhanced the anticancer potential of the 4-thiazolidin one analogues [41].…”

Section: Anticancer Derivativesmentioning

confidence: 99%

“…The in vitro activity as assessed by the MTT assay displayed the remarkable anticancer potential of compound 167a with an IC 50 value of 58.33 μM. The SAR study revealed that the substitution at position 5 of the thiazolidinone scaffold by a substituted‐benzylidene moiety enhanced the anticancer potential of the 4‐thiazolidinone analogues [41].…”

Section: Synthetic Strategies and Biological Activity Profile Of 4‐th...mentioning

confidence: 99%

Synthetic strategies and medicinal perspectives of 4‐thiazolidinones: Recent developments and structure–activity relationship studies

Chawla

Wahan

Negi

et al. 2022

Journal of Heterocyclic Chem

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The 4‐thiazolidinone moiety is a privileged scaffold showing diversity in biological responses like antiinflammatory, antidiabetic, anticancer, antitubercular, anesthetic, hypnotic, antiviral and many more. As a result of this, researchers have been studying and synthesizing this class of heterocycles through several simple as well as complex pathways as the target scaffold for biological studies. This review recapitulates the recent advances in the chemical and biological activities of 4‐thiazolidinones that have proved to be of immense importance in the discovery and development of several molecules and, thereby, the treatment of many ailments. This study will add to previously published reviews by examining the research on various biological activities of 4‐thiazolidinones, including patents, with a focus on structure–activity relationship (SAR) investigations. Literature and patents emphasizing synthetic schemes and biological activities of 4‐thiazolidinones have covered the data in the last decade. Here, sufficient efforts have been put into place to compile the synthetic strategies, establish SARs and enlist various patents so far for this fantastic molecule. The facile synthetic schemes and a vast range of biological activity profiles possessed by this nucleus may provide researchers with new opportunities toward novel therapeutics.

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“…Overexpression of VEGFR1 has been associated with a poor prognosis, as it is thought to contribute to tumor growth and metastasis. [11] Thiazolidin-4-one and its derivatives have a wide range of pharmacological activities such as anticancer [12][13][14][15][16][17] anti-inflammatory, analgesic, anticonvulsant, antimicrobial, local and spinal anesthetics, central nervous system stimulants, hypnotics, anti-HIV, antidiabetic, follicle-stimulating hormone receptor antagonist. [18][19][20][21][22] The aim of this study is to develop new and effective anticancer agents through the synthesis of thiazolidin-4-one derivatives of 4-furfuryloxy-benzohydrazide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

2023

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In this study, 16 new compounds were synthesized starting from methylparaben. These new compounds consist of eight arylidenehydrazide derivatives and eight thiazolidin‐4‐on derivatives. All compounds were tested against MCF‐7 breast cancer cells and MCF10A breast healthy tissue to determine their anti‐cancer activity. Molecular docking studies were also carried out against receptor proteins related to the growth factor of cancer cells to understand inhibition mechanism. According to the results, 4‐furan‐2‐ylmethoxy)‐N‐(4‐oxo‐2‐phenylthiazolidin‐3‐yl)benzamide (5 a) and 4‐(furan‐2‐ylmethoxy)‐N‐(2‐(4‐nitrophenyl)‐4‐oxothiazolidin‐3‐yl)benzamide (5 e) were found as the highest selective and most active compounds against breast cancer cells.

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Synthesis of some 5‐arylidene‐2‐(4‐acetamidophenylimino)‐thiazolidin‐4‐one derivatives and exploring their breast anticancer activity

Cited by 18 publications

References 31 publications

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

Synthetic strategies and medicinal perspectives of 4‐thiazolidinones: Recent developments and structure–activity relationship studies

Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

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