Aminothiazoles and aminothiadiazoles as nucleophiles in aminocarbonylation of iodobenzene derivatives

Gergely, Máté; Kollár, László

doi:10.1016/j.tet.2018.03.007

Cited by 5 publications

(3 citation statements)

References 46 publications

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“…Several groups reported the synthesis of Ntz analogs using acyl chloride derivatives; in other cases EDCI and HOBt or aminocarbonylation followed by iodobenzene substituted reaction were used. All of the methods reported moderate to good yields [50][51][52][53]. Recently, our group reported the successful use of oxyma (ethylcianoacetate oxime), in combination with DIC for solid phase peptide synthesis (SPPS) or with EDCI for solution macrocylization [54].…”

Section: Analogs Synthesismentioning

confidence: 99%

Synthesis and antiplasmodial assessment of nitazoxanide and analogs as new antimalarial candidates

et al. 2022

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During the last years, the progression to control malaria disease seems to be slowed and WHO (World Health Organization) reported a modeling analysis with the prediction of the increase in malaria morbidity and mortality in sub-Saharan Africa during the COVID-19 pandemic. A rapid way to the discovery of new drugs could be carried out by performing investigations to identify drugs based on repurposing of "old" drugs. The 5-nitrothiazole drug, Nitazoxanide was shown to be active against intestinal protozoa, human helminths, anaerobic bacteria, viruses, etc. In this work, Nitazoxanide and analogs were prepared using two methodologies and evaluated against P. falciparum 3D7. A bithiazole analog, showed attractive inhibitory activity with an EC 50 value of 5.9 μM, low propensity to show toxic effect against HepG2 cells at 25 μM, and no cross-resistance with standard antimalarials.

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Section: Analogs Synthesismentioning

confidence: 99%

Synthesis and antiplasmodial assessment of nitazoxanide and analogs as new antimalarial candidates

et al. 2022

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“…Several groups reported the synthesis of Ntz analogues using acyl chloride derivatives; in other cases EDCI and HOBt or aminocarbonylation followed by iodobenzene substituted reaction were used. All of the methods reported moderate to good yields [50][51][52][53]. Recently, our group reported the successful use of oxyma (ethylcianoacetate oxime), in combination with DIC for SPPS (Solid Phase Peptide Synthesis) or with EDCI for solution macrocylization [54].…”

Section: -Analogues Synthesismentioning

confidence: 99%

Synthesis And Antiplasmodial Assessment of Nitazoxanide And Analogues As New Antimalarial Candidates

Irabuena

Scarone

Souza

et al. 2021

Preprint

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During the last years, the progression to control malaria disease seems to be slowed and WHO (World Health Organization) reported a modelling analysis with the prediction of the increase in malaria morbidity and mortality in sub-Saharan Africa during the COVID-19 pandemic. A rapid way to the discovery of new drugs could be carried out by performing investigations to identify drugs based on repurposing of “old” drugs. The 5-nitrothiazole drug, Nitazoxanide was shown to be active against intestinal protozoa, human helminths, anaerobic bacteria, viruses, etc. In this work, Nitazoxanide and analogues were prepared using two methodologies and evaluated against P. falciparum 3 D7. A bithiazole analogue, showed attractive inhibitory activity with an EC50 value of 5.9 mM and low propensity to show toxic effect against HepG2 cells at 25 mM.

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“…Carboxamides can be synthesized from easily available starting materials with aminocarbonylation, although the conventional carboxylic acid−carboxylic halide−carboxamide route is difficult to prepare because it has no notable yield in the implementation [ 29 , 30 ]. Moreover, our research group has been investigating this reaction in the conventional solvent DMF for years [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ], and thanks to the ascertainments of the groups from Skrydstrup [ 40 ] and Mika [ 41 , 42 , 43 ], our interest has been turned to the investigation of green solvents.…”

Section: Introductionmentioning

confidence: 99%

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

et al. 2023

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In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh3. Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles.

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Aminothiazoles and aminothiadiazoles as nucleophiles in aminocarbonylation of iodobenzene derivatives

Cited by 5 publications

References 46 publications

Synthesis and antiplasmodial assessment of nitazoxanide and analogs as new antimalarial candidates

Synthesis and antiplasmodial assessment of nitazoxanide and analogs as new antimalarial candidates

Synthesis And Antiplasmodial Assessment of Nitazoxanide And Analogues As New Antimalarial Candidates

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

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