New Antiparasitic Bis‐Naphthoquinone Derivatives

Jentzsch, Jana; Koko, Waleed S.; Nasr, Ibrahim Al; Khan, Tariq A.; Schobert, Rainer; Ersfeld, Klaus; Biersack, Bernhard

doi:10.1002/cbdv.201900597

Cited by 19 publications

(29 citation statements)

References 17 publications

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“…Compounds 2a-2o were prepared by Knoevenagel reaction of malononitrile and the respective aryl aldehyde under basic conditions followed by Michael addition of lawsone (1a) and ring-closure to the pyran ring in a multi-component one-pot reaction (Scheme 1). [25,26] Compounds 2a-2o were obtained as yellow, brown or red-orange solids in moderate yields.…”

Section: Resultsmentioning

confidence: 99%

“…The Vero cells in 96‐Well plates were cultured in RPMI 1640 medium (5×10 3 cells/well in 200 μL) with 10 % heat inactivated fetal bovine serum (FBS, Invitrogen, USA) in a humidified 5 % CO 2 atmosphere at 37 °C. The inhibition assay with the T. gondii parasites in Vero cells was carried out as described previously [25,39] …”

Section: Methodsmentioning

confidence: 99%

“…The inhibition assay with the T. gondii parasites in Vero cells was carried out as described previously. [25,39] Leishmania major Cell Isolation and Culture Conditions Promastigotes of L. major were isolated in February 2016 and maintained in Schneider's Drosophila medium (Invitrogen, USA), which was supplemented with 10 % FBS and antibiotics, in a tissue culture flask with weekly transfers at 26°C. Promastigotes were cryopreserved in liquid nitrogen at concentrations of 3 × 10 6 parasite/mL.…”

Section: Toxoplasma Gondii Cell Line Culture Conditions and Assaymentioning

confidence: 99%

“…The assay was carried out as reported previously. [47,48] Antioxidant Assay Aliquots of eight concentrations (1,5,10,20,25,50,100, and 150 μM) of test compounds dissolved in methanol were added to eight test tubes. Compounds were accurately dissolved in methanol to achieve the required concentrations by dilution techniques.…”

Section: Leishmania Major Cell Assaysmentioning

confidence: 99%

“…[3,[19][20][21][22][23] Our own previous works have led to the identification of lawsone Mannich bases and naphthoquinone derivatives (1b -1d) with reasonable activities against Trypanosoma brucei, Entamoeba histolytica, L. major or T. gondii (Figure 1). [3,24,25] The fusion of the lawsone scaffold with heterocyclic rings such as pyrans can be another promising method in order to obtain new active compounds based on lawsone and various anti-tumor active derivatives as well as tumor cell senescence-inducing complexes were already identified (1e). [26,27] In continuation of these previous reports, we present new lawsone-derived pyranonaphthoquinone derivatives and their antioxidant and antiparasitic activities against T. brucei, L. major and T. gondii.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

New Pyrano‐4H‐benzo[g]chromene‐5,10‐diones with Antiparasitic and Antioxidant Activities

Nasr

Jentzsch

Shaikh

et al. 2020

Chemistry & Biodiversity

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New pyranonaphthoquinone derivatives were synthesized and investigated for their activity against Trypanosoma brucei, Leishmania major, and Toxoplasma gondii parasites. The pentafluorophenyl derivative was efficacious against T. brucei with single digit micromolar EC 50 values and against T. gondii with even submicromolar values. The 3-chloro-4,5-dimethoxyphenyl derivative showed an activity against amastigotes of Leishmania major parasites comparable to that of amphotericin B. In addition, antioxidant activities were observed for the bromophenyl derivatives, and their redox behavior was studied by cyclovoltammetry. Antiparasitic and antioxidative activities of the new naphthoquinone derivatives appear uncorrelated.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Toxoplasma Gondii Cell Line Culture Conditions and Assaymentioning

confidence: 99%

Section: Leishmania Major Cell Assaysmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

New Pyrano‐4H‐benzo[g]chromene‐5,10‐diones with Antiparasitic and Antioxidant Activities

Nasr

Jentzsch

Shaikh

et al. 2020

Chemistry & Biodiversity

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Silver–N‐heterocyclic carbene complexes‐catalyzed multicomponent reactions: Synthesis, spectroscopic characterization, density functional theory calculations, and antibacterial study

Mnasri

Mejri

Al-Hazmy

et al. 2021

Archiv der Pharmazie

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Nowadays, silver–N‐heterocyclic carbene (silver–NHCs) complexes are widely used in medicinal chemistry due to their low toxic nature toward humans. Due to the success of silver–NHCs in medicinal applications, interest in these compounds is rapidly increasing. Therefore, the interaction of N,N‐disubstituted benzimidazolium salts with Ag2O in dichloromethane to prepare novel Ag(I)–NHCs complexes was carried out at room temperature for 120 h in the absence of light. The obtained complexes were identified and characterized by 1H and 13C nuclear magnetic resonance, Fourier‐transform infrared, UV–Vis, and elemental analysis techniques. Then, the silver complexes were applied for three‐component coupling reactions of aldehydes, amines, and alkynes. The effect of changing the alkyl substituent on the NHCs ligand on the catalytic performance was investigated. In addition, it has been found that the complexes are antimicrobially active and show higher activity than the free ligand. The silver–carbene complexes showed antimicrobial activity against specified microorganisms with MIC values between 0.24 and 62.5 μg/ml. These results showed that the silver–NHC complexes exhibit an effective antimicrobial activity against bacterial and fungal strains. A density functional theory calculation study was performed to identify the stability of the obtained complexes. All geometries were optimized employing an effective core potential basis, such as LANL2DZ for the Ag atom and 6‐311+G(d,p) for all the other atoms in the gas phase. Electrostatic potential surfaces and LUMO–HOMO energy were computed. Transition energies and excited‐state structures were obtained from the time‐dependent density functional theory calculations.

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Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

Jelali

Nasr

Koko

et al. 2022

Journal of Heterocyclic Chem

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In this work, efficient synthesis of isoindolin-1-one-3-phosphonates under catalyst-and solvent-free conditions was reported to afford the desired compounds in excellent yields with potent pharmacological properties. The synthesis method involves the preparation of isoindolin-1-one-3-phosphonates by a "one-pot" three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent-and catalyst-free conditions.All new compounds were characterized by 1 H NMR, 13 C NMR, FT-IR and elemental analysis techniques. The compounds were investigated for their bioactivities against a group of microorganisms, Leishmania major, Toxoplasma gondii parasites, and the DA-MB-231 and MCF-7 cancer cell lines in vitro.Compound 4a was found to be the most active against L. M. luteus, L. monocytogenes and C. albicans microorganisms, with inhibition zones of 35, 22 and 38 mm, respectively. The compounds were also investigated for their antiparasitic activities, and compounds 4a and 4b were the most active against L. major amastigotes and promastigotes with EC 50 < 1 μM. All tested compounds had potent anticancer activity against the MDA-MB-231 and MCF-7 human cell lines with EC 50 < 1.5 μM. Compounds 4a and 4b are good drug candidates for antimicrobial, antileishmanial and anticancer drug discovery, and further in vivo studies are highly recommended prior to any clinical trials.

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New Antiparasitic Bis‐Naphthoquinone Derivatives

Cited by 19 publications

References 17 publications

New Pyrano‐4H‐benzo[g]chromene‐5,10‐diones with Antiparasitic and Antioxidant Activities

New Pyrano‐4H‐benzo[g]chromene‐5,10‐diones with Antiparasitic and Antioxidant Activities

Silver–N‐heterocyclic carbene complexes‐catalyzed multicomponent reactions: Synthesis, spectroscopic characterization, density functional theory calculations, and antibacterial study

Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

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