Synthesis, characterization and biological assessment of a novel hydrazone as potential anticancer agent and enzyme inhibitor

Noma, Samir Abbas Ali; Erzengin, Mahmut; Tunç, Tuncay; Balcıoğlu, Sevgi

doi:10.1016/j.molstruc.2019.127550

Cited by 20 publications

(12 citation statements)

References 26 publications

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“…As an important class of medicinal chemistry, many of the differently substituted acyl hydrazones [ 21 , 22 , 23 , 24 , 25 , 26 ] and 1,3,4 oxadiazole derivatives [ 27 , 28 , 29 , 30 , 31 , 32 ] are already in the structures of some agents that are being used against cancer. The structures of some of those agents are shown in Figure 1 below.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

et al. 2022

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To understand whether previously synthesized novel hydrazone and oxadiazole derivatives have promising anticancer effects, docking studies and in vitro toxicity assays were performed on A-549, MDA-MB-231, and PC-3 cell lines. The antiproliferative properties of the compounds were investigated using molecular docking experiments. Each compound’s best-docked poses, binding affinity, and receptor-ligand interaction were evaluated. Compounds’ molecular weights, logPs, TPSAs, abilities to pass the blood-brain barrier, GI absorption qualities, and CYPP450 inhibition have been given. When the activities of these molecules were examined in vitro, for the A-549 cell line, hydrazone 1e had the minimum IC50 value of 13.39 μM. For the MDA-MB-231 cell line, oxadiazole 2l demonstrated the lowest IC50 value, with 22.73 μM. For PC-3, hydrazone 1d showed the lowest C50 value of 9.38 μM. The three most promising compounds were determined as compounds 1e, 1d, and 2a based on their minimum IC50 values, and an additional scratch assay was performed for A-549 and MDA-MB-231 cells, which have high migration capacity, for the three most potent molecules; it was determined that these molecules did not show a significant antimetastatic effect.

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Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

et al. 2022

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“…These derivatives are thought to be an important source for obtaining anti-bacterial, antioxidant, antifungal, anti-inflammatory, and anticancer activities. [9,10] Hydrazone derivatives of flurbiprofen were shown to have anticancer activity against ovarian and leukemia cancer cell lines, [11] and acetyl hydrazone derivatives exhibited antitumor activity against Hep G2 hepatocarcinoma cells with an acceptable IC 50 value, the phenyl ring of hydrazone was found to have a substantial role in this activity. [12] Moreover, indole hydrazone derivatives showed a selective and effective cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of 5‐Bromoindole‐2‐Carboxylic Acid Hydrazone Derivatives: In Vitro Anticancer and VEGFR‐2 Inhibitory Effects

et al. 2022

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A new set of 5‐bromoindole‐2‐carboxylic acid hydrazone derivatives were synthesized and studied as potential inhibitors of VEGFR‐2 tyrosine kinase (TK). Various physical (color, melting point, etc.) and spectroscopic (IR, 1H NMR, 13C NMR, and MS) methods were used to determine the structure of the novel 5‐bromoindole hydrazone derivatives. A molecular docking study revealed that 5‐bromo‐N′‐(4‐hydroxy or 4‐chloro or 4‐(dimethyl amino) benzylidene or furan‐2‐ylmethylene)‐1H‐indole‐2‐carbohydrazide derivatives had the best binding energies against the VEGFR TK domain. All of the newly synthesized compounds displayed adequate absorption levels and did not appear to inhibit cytochrome P450. Furthermore, they did not show in silico hepatotoxicity. The novel indole hydrazone derivatives inhibited cell proliferation (measured by the MTT assay) in three human cancer cell lines tested, with the 5‐bromo‐N′‐(4‐(dimethyl amino) benzylidene)‐1H‐indole‐2‐carbohydrazide derivative (5BDBIC) being the most potent against Hep G2 hepatocellular carcinoma cells (IC50=14.3 μM), and almost similar to that of the standard VEGFR TK inhibitor sorafenib (IC50=6.2 μM). Compound 5BDBIC inhibited VEGFR‐2 TK activity leading to cell cycle arrest at the G2/M phase, and induction of the intrinsic apoptosis pathway. In conclusion, compound 5BDBIC is a promising antitumor agent that targets the tyrosine kinase activity of VEGFR.

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“…In this study, some of the tested compounds displayed higher anticancer activity than cisplatin. 15 Hydrazone structures play an important role in anticancer-related processes, as mentioned in the examples above.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some Hydrazide-Hydrazone Derivatives as Anticancer Agents

Akdağ

Tok

Karakuş

et al. 2022

ACSi

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In this study, a series of hydrazide-hydrazone derivatives (3a-3u) were synthesized and evaluated for their anticancer activitiesagainst prostate cancer cell line (PC-3), breast cancer cell line (MCF-7), colon cancer cell line (HT-29) and human umbilical vein endothelial cells (HUVEC) using MTT assay. In particular, compound 3h having a pyrrole ring was found to be the most potent derivative with IC50 = 1.32, 2.99, 1.71 μM against PC-3, MCF-7, HT-29 cancer cell lines respectively using paclitaxel as a standard compound. Furthermore, compound 3h was subjected to further biological studies such as caspase-3 activity and Annexin-V assay to evaluate their inhibitory potentials. The activity results displayed that compound 3h increased caspase-3 activation and the number of cells to early apoptosis. The additional studies like pharmacokinetics, bioavailability scores and drug-likeness properties were also evaluated. The in silico pharmacokinetics predictions displayed that the bioavailability of these compounds may be high.

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Synthesis, characterization and biological assessment of a novel hydrazone as potential anticancer agent and enzyme inhibitor

Cited by 20 publications

References 26 publications

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

Design, Synthesis, and Molecular Docking Studies of 5‐Bromoindole‐2‐Carboxylic Acid Hydrazone Derivatives: In Vitro Anticancer and VEGFR‐2 Inhibitory Effects

Synthesis and Biological Evaluation of Some Hydrazide-Hydrazone Derivatives as Anticancer Agents

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