Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Han, M. İhsan; Bekçi, Hatice; Cumaoğlu, Ahmet; Küçükgüzel, Ş. Güniz

doi:10.12991/jrp.2018.98

Cited by 18 publications

(35 citation statements)

References 23 publications

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“…As a result of this, many researchers have synthesized new hydrazide-hydrazones as aimed structures and evaluated their various activities [7][8][9][10][11][12][13]. It has been noticed that hydrazide-hydrazones have anticancer activity in previous studies [14][15][16][17][18][19][20][21][22][23]. Thus, we focused our interest on the hydrazide-hydrazone structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben

Han¹,

Atalay²,

İmamoğlu³

et al. 2020

jrp

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Parabens, which are hydroxybenzoic acid esters, are particularly used as protective against mold and fungus. Ethyl paraben is a compound open to modification for the synthesis of new molecules due to the ester group in its structure. In this study, ethyl paraben was used as a starting material. A new series of novel hydrazide-hydrazones from derived ethyl paraben were synthesized and characterized by spectroscopic techniques such as NMR, FT-IR besides elemental analysis. In order to determine the anticancer activity of the aimed ethyl paraben hydrazidehydrazones we evaluated their cytotoxic activity on liver cancer cell line liver hepatocellular carcinoma (HepG2). Herein we described several 4-hydroxy-N'-[substituted methylidene] benzohydrazides (3a-j) as anticancer agents. We designed, synthesized and characterized the series of novel hydrazide-hydrazones from ethyl paraben. All of the compounds evaluated for anticancer activity by using MTT assay for 24 and 48 h. mRNA transcription levels of Bax, Bcl-2 and caspase-3 genes were determined by realtime polymerase chain reaction (qRT-PCR) analysis. Compounds 3i and 3j showed anticancer activity with 42.4 and 37.4 µM IC50 values, respectively. Doxorubicin was used as a positive sensitivity reference standard. qRTPCR analysis approved that there was a timedependent rise in the expression levels of Bax, Bcl-2 and Caspase 3 on apoptosis. The activities of the synthesized compounds changed depending on the dose and time of treatment and some of the molecules started to show activity within 48 hours.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben

Han¹,

Atalay²,

İmamoğlu³

et al. 2020

jrp

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“…Ethyl {[4‐(4‐fluorophenyl)‐5‐[(1‐(6‐methoxynaphtalene‐2‐yl)ethyl)]‐4 H ‐1,2,4‐triazole‐3‐yl]sulphanyl}acetate ( 5 ) was prepared in a solution of compound 4 and acetone with equimolar ethyl bromoacetate and double as much mole of potassium carbonate. 2‐({5‐[1‐(6‐Methoxynaphtalene‐1‐yl)ethyl]‐4‐fluorophenyl‐4 H ‐1,2,4‐triazole‐3‐yl}sulphanyl)acetohydrazide ( 6 ) was synthesized with compound 5 and hydrazine hydrate 80% in solution of ethanol . Our final compounds hydrazide–hydrazones ( 7a–m ) were synthesized with compound 6 and chosen aromatic aldehydes in a few drops of glacial acetic acid in ethanolic medium.…”

Section: Resultsmentioning

confidence: 99%

“…As in the European Pharmacopoeia (EP) monograph, 0.5 g of naproxen was dissolved in 25 ml of pure ethanol. The measurement results (+59.246) are in the form of ( S )‐naproxen according to the results of EP 7.0 (+59–+62) …”

Section: Resultsmentioning

confidence: 99%

“…We applied a computational work to the prediction of absorption, distribution, metabolism, and excretion (ADME) properties of the molecules by determination of lipophilicity, topological polar surface area (TPSA), absorption (% ABS) and simple molecular descriptors used by Lipinski in formulating his “rule of five.” Calculations were performed utilizing Molinspiration on‐line property calculation toolkit (http://www.molinspiration.com; Table ). The formulation of % ABS = 109 – (0.345 × TPSA) was used for estimating percentage of absorption (% ABS) …”

Section: Resultsmentioning

confidence: 99%

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Synthesis, molecular modeling, in vivo study, and anticancer activity of 1,2,4‐triazole containing hydrazide–hydrazones derived from (S)‐naproxen

Han

Bekçi

Uba

et al. 2019

Archiv der Pharmazie

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A new series of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)naproxen (7a-m) was synthesized in this study. The structures of these compounds were characterized by spectral (Fourier-transform infrared spectroscopy, 1 H-nuclear magnetic resonance (NMR), 13 C-NMR, and high-resolution electron ionization mass spectrometry) methods. Furthermore, molecular modeling of these compounds was studied on human methionine aminopeptidase-2. All synthesized compounds were screened for anticancer activity against three prostate cancer cell lines (PC3, DU-145, and LNCaP) using the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4sulfophenyl)-2H-tetrazolium colorimetric method. Compound 7a showed the best activity against the PC3, DU-145 and LNCaP cancer cell lines with IC 50 values of 26.0, 34.5, and 48.8 μM, respectively. Compounds 7b, 7k, and 7m showed anticancer activity against cancer cell lines PC3 and DU-145 with IC 50 values of 43.0, 36.5, 29.3 μM and 49.8, 49.1, 31.6 μM, respectively. Compounds 7f and 7g showed anticancer activity against PC3 cells with IC 50 values of 43.4 and 34.5 μM, respectively. To assess the biodistribution in mice of IRDye800, dye-labeled compound 7a or 100 μM of free dye was injected intravenously into the mice's tail. In vivo images were taken with in vivo imaging system spectrum device at 60, 120, 180, 240, 300, and 360 min after injection.At the end of 360 min, ex vivo studies were carried out to determine in which organs the dye was accumulated in the urogenital system. Ex vivo studies showed that the accumulation of compound 7a in the prostate is greater than that of the free dye, and it is concluded that compound 7a may be promising for the treatment of prostate cancer.

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“…Besides antimicrobial [10,11], anti-inflammatory [10,12], antituberculosis [13], antifungal [14], and herbicidal properties [15], antitumor activity has been reported [16], e.g., in the anticancer drugs letrozole, anastrozole, and vorozole [17]. Meanwhile, more and more new 1,2,4-triazole anticancer compounds are being studied [18,19]. In addition, many sulfonamide compounds with antitumor activity have been reported in recent years [20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety

et al. 2020

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Seventeen novel 2-(5-amino-1-(substituted sulfonyl)-1H-1,2,4-triazol-3-ylthio)-6- isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one compounds were synthesized from the abundant and naturally renewable longifolene and their structures were confirmed by FT-IR, NMR, and ESI-MS. The in vitro cytotoxicity of the synthesized compounds was evaluated by standard MTT assay against five human cancer cell lines, i.e., T-24, MCF-7, HepG2, A549, and HT-29. As a result, compounds 6d, 6g, and 6h exhibited better and more broad-spectrum anticancer activity against almost all the tested cancer cell lines than that of the positive control, 5-FU. Some intriguing structure–activity relationships were found and are discussed herein by theoretical calculation.

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Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Cited by 18 publications

References 23 publications

Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben

Synthesis, characterization and anticancer activity of novel hydrazide-hydrazones derived from ethyl paraben

Synthesis, molecular modeling, in vivo study, and anticancer activity of 1,2,4‐triazole containing hydrazide–hydrazones derived from (S)‐naproxen

Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety

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