Synthesis, molecular modeling, in vivo study and anticancer activity against prostate cancer of (+) (S)-naproxen derivatives

Birgül, Kaan; Yıldırım, Yeliz; Karasulu, H. Yeşim; Karasulu, Ercüment; Uba, Abdullahi Ibrahim; Bekçi, Hatice; Cumaoğlu, Ahmet; Kabasakal, Levent; Yılmaz, Özgür; Küçükgüzel, Ş. Güniz

doi:10.1016/j.ejmech.2020.112841

Cited by 26 publications

(20 citation statements)

References 27 publications

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“…The molecular weights of the synthesized compounds Naproxen is a well knownnon-steroidal antiinflammatory drug (NSAIDs) that acts as a COX inhibitor [10]. In addition to theiranti-inflammatory activity, naproxen derivatives have been explored for anticancer activity [11][12][13][14][15]. For example, Naproxen-based urea and propanamide derivatives have shown promising inhibition in colon cancer cells [16], protection in bladder cancer proliferation [17] and inhibitors of VEGFR-2 and histone deacetylase enzymes [18,19].…”

Section: Generalmentioning

confidence: 99%

“…The molecular weights of the synthesized compounds were measured on a mass spectrometer (LCQ Fleet-LCF10605) and elemental analyses were performed on a LEECO Elementar Analyzer. (8)(9)(10)(11)(12)(13)(14)(15)(16) The target compounds (8)(9)(10)(11)(12)(13)(14)(15)(16) were prepared according to our previous work [31] with fewmodifications. The key intermediate 5 (0.001 mole) was charged into a round bottom flask (100 mL) followed by the addition of ter.butanol:water (2:1, 50 mL).…”

Section: Generalmentioning

confidence: 99%

“…The MDC layer was concentrated and recrystallized using MDC and cyclohexane (Scheme 1). The target compounds (8)(9)(10)(11)(12)(13)(14)(15)(16) were prepared according to our previous work [31] with fewmodifications. The key intermediate 5 (0.001 mole) was charged into a round bottom flask (100 mL) followed by the addition of ter.butanol:water (2:1, 50 mL).…”

Section: Generalmentioning

confidence: 99%

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Naproxen Based 1,3,4-Oxadiazole Derivatives as EGFR Inhibitors: Design, Synthesis, Anticancer, and Computational Studies

et al. 2021

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A library of novel naproxen based 1,3,4-oxadiazole derivatives (8–16 and 19–26) has been synthesized and screened for cytotoxicity as EGFR inhibitors. Among the synthesized hybrids, compound2-(4-((5-((S)-1-(2-methoxynaphthalen-6-yl)ethyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)phenol(15)was the most potent compound against MCF-7 and HepG2cancer cells with IC50 of 2.13 and 1.63 µg/mL, respectively, and was equipotent to doxorubicin (IC50 1.62 µg/mL) towards HepG2. Furthermore, compound 15 inhibited EGFR kinase with IC50 0.41 μM compared to standard drug Erlotinib (IC50 0.30 μM). The active compound induces a high percentage of necrosis towards MCF-7, HePG2 and HCT 116 cells. The docking studies, DFT and MEP also supported the biological data. These results demonstrated that these synthesized naproxen hybrids have EGFR inhibition effects and can be used as leads for cancer therapy.

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Section: Generalmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

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Naproxen Based 1,3,4-Oxadiazole Derivatives as EGFR Inhibitors: Design, Synthesis, Anticancer, and Computational Studies

et al. 2021

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“…Structures containing a 1,2,4-triazole ring have anticancer activity. 36–46 There exist a few molecules with a 1,2,4-triazole ring used in breast cancer, such as Vorozole, Anastrazole, and Letrozole (Scheme 1). 47,48…”

Section: Introductionmentioning

confidence: 99%

“…Structures containing a 1,2,4-triazole ring have anticancer activity. [36][37][38][39][40][41][42][43][44][45][46] There exist a few molecules with a 1,2,4-triazole ring used in breast cancer, such as Vorozole, Anastrazole, and Letrozole (Scheme 1). 47,48 In this study, we synthesized novel (S)-Naproxen thiosemicarbazide (3a-m) and 1,2,4-triazole derivatives (4a-j) and investigated their anticancer activity against breast cancer cell line MDA-MB-231.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and in vitro and in vivo anticancer activity studies of new (S)-Naproxen thiosemicarbazide/1,2,4-triazole derivatives

et al. 2022

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Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Han

İnce

Gündüz

et al. 2022

Chemistry & Biodiversity

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The discovery of new antimicrobial molecules is crucial for combating drug‐resistant bacterial and fungal infections that pose a dangerous threat to human health. In the current research, we applied a molecular hybridization approach to synthesize original thiosemicarbazide‐triazole derivatives starting from (S)‐naproxen (7a–7k). After structural characterization using FT‐IR, 1H‐NMR, 13C‐NMR, and HR‐MS, the obtained compounds were screened for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Candida albicans ATCC 10231 and their isolates, as well. Although all compounds were found to be moderate antimicrobial agents, in general, their antibacterial activities were better than antifungal effects. Among the tested compounds, 7j carrying nitrophenyl group on the thiosemicarbazide functionality represented the best MIC value against S. aureus isolate. Finally, molecular docking studies were performed in the active pocket of S. aureus flavohemoglobin to rationalize the obtained biological data.

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Synthesis, molecular modeling, in vivo study and anticancer activity against prostate cancer of (+) (S)-naproxen derivatives

Cited by 26 publications

References 27 publications

Naproxen Based 1,3,4-Oxadiazole Derivatives as EGFR Inhibitors: Design, Synthesis, Anticancer, and Computational Studies

Naproxen Based 1,3,4-Oxadiazole Derivatives as EGFR Inhibitors: Design, Synthesis, Anticancer, and Computational Studies

Design, synthesis, and in vitro and in vivo anticancer activity studies of new (S)-Naproxen thiosemicarbazide/1,2,4-triazole derivatives

Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

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