Synthesis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from $N$-(arylsulfonyl)methionine

Tatar, Esra; Şenkardeş, Sevil; Sellitepe, Hasan Erdinç; Küçükgüzel, Ş. Güniz; Karaoğlu, Şengül Alpay; Bozdeveci, Arif; Clercq, Erik De; Pannecouque, Christophe; Hadda, Taïbi Ben; Küçükgüzel, İlkay

doi:10.3906/kim-1509-21

Cited by 21 publications

(10 citation statements)

References 52 publications

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“…The activity of hydrazide-hydrazones is known to be associated with the active pharmacophoric group. 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].…”

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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“…As well as other NSAIDs, naproxen was reported to be efficient in the prevention of many cancers [3][4][5]. Hydrazide-hydrazones [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and 1,2,4-triazole rings [22][23][24][25][26] have diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

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

Han¹,

Bekçi²,

Cumaoğlu³

et al. 2018

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How to cite this article: Han M, Bekçi H, Cumaoğlu A, Küçükgüzel ŞG. Synthesis and characterization of 1,2,4-triazole containing hydrazidehydrazones derived from (S)-Naproxen as anticancer agents. Marmara Pharm J. 2018; 22 (4): 559-569. ABSTRACT: A novel series of new naproxen derivativeswere synthesized, in this study. The structures of compounds 5, 6 and 7a-m were defined by spectral ( 1 H-NMR, 13 C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography. These compounds were evaluated for in vitro anticancer activity by using MTS method against PC-3 and DU-143 (androgen-independent human prostate cancer cell lines) and LNCaP (androgen-sensitive human prostate adenocarcinoma) prostate cancer cell lines. Cisplatin was used as the positive sensitivity reference standard. Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

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“…POM physicochemical analysis or ADME/T is important to qualify drugs and their efficacy as leading candidates against various biotargets, as like antibacterial (Grib et al, 2020;Hatzade et al, 2015;Jamalis et al, 2020;Jarrahpour et al,2019;Mabkhot et al, 2015Mabkhot et al, , 2016Messali et al, 2014Messali et al, , 2015Nasruddin et al, 2018;Rad et al, 2017;Rbaa et al, 2019;Sajid et al, 2016;Tatar et al, 2016), antifungal (Al-Maqtari et al, 2017Khan et al, 2017;Rachedi et al, 2020;Radi et al, 2015;Tighadouni et al, 2016;Titi et al, 2019), antiviral (Chander et al, 2017;Lahsasni et al, 2015), antitumoral (Bechlem et al, 2020;Kamal et al, 2019;Piaz et al, 2018;Rachedi et al, 2019Rachedi et al, , 2020Youssoufi et al, 2015), antiparasitic drugs and various enzymes inhibitors (Amirkhanov et al, 2019;Ben Hadda et al, 2018Mabkhot et al, 2014;Rauf et al, 2017). The POM physicochemical calculations included a partition coefficient (cLogP), aqueous solubility, donor hydrogen bond, and drug-likeness, evaluated in terms of Lipinski's ruleof-five.…”

Section: Pom Analyses and Identification Of Pharmacophore Sitesmentioning

confidence: 99%

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

Hadda

Berredjem

Almalki

et al. 2021

Journal of Biomolecular Structure and Dynamics

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Remdesivir and hydroxychloroquine derivatives form two important classes of heterocyclic compounds. They are known for their anti-malarial biological activity. This research aims to analyze the physicochemical properties of remdesivir and hydroxychloroquine compounds by the computational approach. DFT, docking, and POM analyses also identify antiviral pharmacophore sites of both compounds. The antiviral activity of hydroxychloroquine compound's in the presence of zinc sulfate and azithromycin is evaluated through its capacity to coordinate transition metals (M = Cu, Ni, Zn, Co, Ru, Pt). The obtained bioinformatic results showed the potent antiviral/antibacterial activity of the prepared mixture (Hydroxychloroquine/Azithromycin/Zinc sulfate) for all the opportunistic Gram-positive, Gram-negative in the presence of coronavirus compared with the complexes Polypyridine-Ruthenium-di-aquo. The postulated zinc(II) complex of hydroxychloroquine derivatives are indeed an effective antibacterial and antiviral agent against coronavirus and should be extended to other pathogens. The combination of a pharmacophore site with a redox [Metal(OH 2 ) 2 ] moiety is of crucial role to fight against viruses and bacteria strains. Communicated by Ramaswamy H. Sarma

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Synthesis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from $N$-(arylsulfonyl)methionine

Cited by 21 publications

References 52 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 and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

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