Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

Baddi, Laila; Ouzebla, Driss; Mansouri, Az-Eddine El; Smietana, Michaël; Vasseur, Jean‐Jacques; Lazrek, H. B.

doi:10.1080/15257770.2020.1826516

Cited by 12 publications

(5 citation statements)

References 59 publications

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“…Moreover, alongside the after-mentioned interactions for ligand 7 b, the introduction of thiazole in compound 7 b showed two additional Pi-sulfur and PiÀ Pi T-shaped into reactions with Cys163 and His121, which are among the key amino acids responsible for the caspase-3 activation. [50][51][52][53][54][55] Overall, molecular docking suggested that the anticancer activities of products 2 b and 7 b could be at least mediated by activating caspase-3 protein after binding to its active site.…”

Section: Molecular Docking Studymentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

et al. 2022

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Herein, we report the synthesis of a novel series of βhimachalene derivatives, including semicarbazones, thiosemicarbazones, and thiazoles. The structures of these compounds were elucidated by NMR, IR, and HRMS analysis methods. The in vitro antitumor activity of these compounds was evaluated by the MTT assay against four human cancer cell lines, such as fibrosarcoma (HT-1080), breast adenocarcinoma (MCF-7 and MDA-MB-231), and lung carcinoma (A-549), and the results indicated that all compounds showed moderate to significant cytotoxic activities against all cancer cell lines with IC 50 values ranging from 7.19 � 0.30 to 50 μM. The mechanism of action of the most cytotoxic compounds 2 b and 7 b suggested that they induced apoptosis through caspase-3/7 activation, and elicited G2/M-phase arrest with the loss of mitochondrial membrane potential in HT-1080 cells. The molecular docking showed that compounds 2 b and 7 b activated the caspase-3 by forming a stable protein-ligand complex.

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Section: Molecular Docking Studymentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

et al. 2022

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“…The ligand structure was created separately using ChemDraw Ultra 12.0, energy was minimized in Chem3D, and torsional bonds of the ligand were set to be flexible and saved in PDBQT format. [ 60 ] Next, the receptor was kept rigid and a grid covering all the amino acid residues present inside the active site of proteins was built (grid box size of 50 × 50 × 50 Å with a spacing of 0.375 Å between the grid points and centered at 35.58 [ x ], 94.397 [ y ], and 17.54 [ z ]). The best conformers were searched using the Lamarckian genetic algorithm, the population size was set to 150, and the maximum number of energy evaluations was set to 25,000,000.…”

Section: Methodsmentioning

confidence: 99%

Discovery of novel furo[2,3‐d]pyrimidin‐2‐one–1,3,4‐oxadiazole hybrid derivatives as dual antiviral and anticancer agents that induce apoptosis

Mansouri

Oubella²,

Dânoun

et al. 2021

Archiv der Pharmazie

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A new series of furo[2,3‐d]pyrimidine–1,3,4‐oxadiazole hybrid derivatives were synthesized via an environmentally friendly, multistep synthetic tool and a one‐pot Songoashira‐heterocyclization protocol using, for the first time, nanostructured palladium pyrophosphate (Na2PdP2O7) as a heterogeneous catalyst. Compounds 9a–c exhibited broad‐spectrum activity with low micromolar EC50 values toward wild and mutant varicella‐zoster virus (VZV) strains. Compound 9b was up to threefold more potent than the reference drug acyclovir against thymidine kinase‐deficient VZV strains. Importantly, derivative 9b was not cytostatic at the maximum tested concentration (CC50 > 100 µM) and had an acceptable selectivity index value of up to 7.8. Moreover, all synthesized 1,3,4‐oxadiazole hybrids were evaluated for their cytotoxic activity in four human cancer cell lines: fibrosarcoma (HT‐1080), breast (MCF‐7 and MDA‐MB‐231), and lung carcinoma (A549). Data showed that compound 8f exhibits moderate cytotoxicity, with IC50 values ranging from 13.89 to 19.43 µM. Besides, compound 8f induced apoptosis through caspase 3/7 activation, cell death independently of the mitochondrial pathway, and cell cycle arrest in the S phase for HT1080 cells and the G1/M phase for A549 cells. Finally, the molecular docking study confirmed that the anticancer activity of the synthesized compounds is mediated by the activation of caspase 3.

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“…Amines have also been employed for the synthesis of various α-amino phosphonates 126 via iodine catalyzed MCRs. A Kabachnik-Field reaction of amines, acyclic nucleosides and triethyl phosphate was reported by Baddi et al [124] in one-pot manner using natural phosphate coated with iodine (I 2 @NP) as catalyst (Scheme 63). Aromatic as well as aliphatic amines reacted smoothly to furnish the corresponding α-amino phosphonates 126 in good yield.…”

Section: Synthesis Of Isoquinolonic Acids Phosphonic Acid Acyclic Nuc...mentioning

confidence: 99%

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

et al. 2022

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In multicomponent reactions, three or more reactants combine in one pot to form a product without the isolation of intermediate and most of the reactants contribute to newly formed product reducing number of steps involved and waste generated. Molecular iodine is mild, efficient, relatively nontoxic, inexpensive, commercially available, and catalyzes various organic reactions due to its Lewis acidic behaviour. The development of multicomponent reactions catalyzed by molecular iodine indeed is a good green alternative for synthetic organic chemistry. The aim of this article is to review all important multicomponent reactions catalyzed by molecular iodine reported since 2013 in order to envisage some new efficient protocols for the synthesis of structurally complex molecules.

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Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

Cited by 12 publications

References 59 publications

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

Synthesis and Biological Evaluation of Novel Thiazole Analogs with Both Anti‐Proliferative and Mechanistic Analyses and Molecular Docking Studies

Discovery of novel furo[2,3‐d]pyrimidin‐2‐one–1,3,4‐oxadiazole hybrid derivatives as dual antiviral and anticancer agents that induce apoptosis

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

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