[Retracted] Facile and straightforward synthesis of Hydrazone derivatives

Ain, Noor Ul; Ansari, Tariq Mahmood; Gilani, Muhammad Rehan Hasan Shah; Xu, Guobao; Liang, Gaolin; Luque, Rafael; Alsaiari, Mabkhoot; Jalalah, Mohammed

doi:10.1155/2022/3945810

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…Compared to ketones, the alpha‐hydrogen atom of hydrazones is more nucleophilic because the alpha‐hydrogen atom of hydrazone is 10 times more acidic than ketones. The nucleophilicity of the hydrogen carbon atom is among the most important properties of hydrazones (Ain et al, 2022; Jabeen, 2022). This feature of hydrazide‐hydrazones is the part that enables them to exhibit various biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in silico and in vitro studies of hydrazide‐hydrazone imine derivatives as potential cholinesterase inhibitors

Güngör

2023

Chem Biol Drug Des

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A series of hydrazide‐hydrazone imine derivative compounds (3a–k) were synthesized and their structures characterized using FTIR, 1H, and 13C (NMR) spectroscopic methods. In addition, molecular structures of compounds 3a, 3d, and 3g were elucidated by X‐ray diffraction technique. In vitro inhibition activities of hydrazide‐hydrazone imine derivatives against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) were investigated. Compound 3i (IC50 = 2.01 μM) exhibited the best inhibitory activity against AChE, comparable to the control Galantamine (IC50 = 2.60 μM). Against BChE, compound 3h (IC50 = 2.83 μM) showed the best inhibitory property which is higher control Galantamine (IC50 = 3.70 μM). The Ki values of compound 3i (Ki = 0.63 μM) and compound 3h (Ki = 0.94 μM) that have the strongest inhibitory potential were determined against AChE and BChE, respectively. According to the docking result, the most stable conformation of AChE and compound 3i showed that it has a binding affinity of −10.82 kcal/moL. The binding affinity of the most stable conformation formed by BChE and compound 3h is −8.60 kcal/moL. Finally, in silico results and pharmacokinetic parameters of ADME showed that these compounds have good oral bioavailability properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis, in silico and in vitro studies of hydrazide‐hydrazone imine derivatives as potential cholinesterase inhibitors

Güngör

2023

Chem Biol Drug Des

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“…The hydrazones are stable at neutral pH but are rapidly destroyed in the acidic environment around the tumor, and hence designing a pH-sensitive drug delivery system is an advantage. These characteristics have allowed hydrazones to be linked to many drugs for many applications [1][2][3][4][5][6][7][8][9]. Additionally, hydrazones are good chelating agents due to their ability to form stable complexes with many transition metals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Hirshfeld, DFT Conformational, Cytotoxic, and Anti-Toxoplasma Studies of New Indole-Hydrazone Derivatives

Hassan,

Soliman,

Moneer

et al. 2023

IJMS

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The hydrazones 3a–c, were synthesized from the reaction of indole-3-carbaldehyde and nicotinic acid hydrazide, isonicotinic acid hydrazide, and benzoic acid hydrazide, respectively. Their structures were confirmed using FTIR, 1HNMR, and 13CNMR spectroscopic techniques. Exclusively, hydrazones 3b and 3c were confirmed using single crystal X-ray crystallography to exist in the Eanti form. With the aid of DFT calculations, the most stable configuration of the hydrazones 3a–c in gas phase and in nonpolar solvents (CCl4 and cyclohexane) is the ESyn form. Interestingly, the DFT calculations indicated the extrastability of the EAnti in polar aprotic (DMSO) and polar protic (ethanol) solvents. Hirshfeld topology analysis revealed the importance of the N…H, O…H, H…C, and π…π intermolecular interactions in the molecular packing of the studied systems. Distribution of the atomic charges for the hydrazones 3a–c was presented. The hydrazones 3a–c showed a polar character where 3b has the highest polarity of 5.7234 Debye compared to the 3a (4.0533 Debye) and 3c (5.3099 Debye). Regarding the anti-toxoplasma activity, all the detected results verified that 3c had a powerful activity against chronic toxoplasma infection. Compound 3c showed a considerable significant reduction percent of cyst burden in brain homogenates of toxoplasma infected mice representing 49%.

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“…This article has been retracted by Hindawi following an investigation undertaken by the publisher [1]. This investigation has uncovered evidence of one or more of the following indicators of systematic manipulation of the publication process:…”

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confidence: 99%