One-Pot CuO-Catalyzed Green Synthesis of N(N′)-Arylbenzamidines as Potential Enzyme Inhibitors

Taj, Muhammad Babar; Raheel, Ahmad; Alelwani, Walla; Babteen, Nouf Abubakr; Kattan, Shahad W.; Alnajeebi, Afnan M.; Sharif, Muhammad; Ahmad, Hayat; Аббас,; Hazeeq, A.; Tirmizi, Syed Ahmed; Ali, Hasrat

doi:10.1134/s1070428019070224

Cited by 4 publications

(3 citation statements)

References 27 publications

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“…However, the implementation of the green chemistry principles is still a big challenge, and there are only few reports about the thorough implementation of the latter in the early steps of research towards APIs. Although there are different studies which focus on the green design of inhibitors [30], it remains relatively underexplored, likewise in the design and synthesis of FXa inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Green by Design: Convergent Synthesis, Computational Analyses, and Activity Evaluation of New FXa Inhibitors Bearing Peptide Triazole Linking Units

et al. 2021

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Green chemistry implementation has led to promising results in waste reduction in the pharmaceutical industry. However, the early sustainable development of pharmaceutically active compounds and ingredients remains a considerable challenge. Herein, we wish to report a green synthesis of new pharmaceutically active peptide triazoles as potent factor Xa inhibitors, an important drug target associated with the treatment of diverse cardiovascular diseases. The new inhibitors were synthesized in three steps, featuring cycloaddition reactions (high atom economy), microwave-assisted organic synthesis (energy efficiency), and copper nanoparticle catalysis, thus featuring Earth-abundant metals. The molecules obtained showed FXa inhibition, with IC50-values as low as 17.2 μM and no associated cytotoxicity in HEK293 and HeLa cells. These results showcase the environmental potential and chemical implications of the applied methodologies for the development of new molecules with pharmacological potential.

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Section: Introductionmentioning

confidence: 99%

Green by Design: Convergent Synthesis, Computational Analyses, and Activity Evaluation of New FXa Inhibitors Bearing Peptide Triazole Linking Units

et al. 2021

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“…Using microwave heating process, Taj and coworkers have synthesized novel N(N')arylbenzamidines starting from corresponding N-arylbenzamides with ammonia or aniline in a one-pot reaction. The synthesized compounds showed good inhibition activity against several enzymes including acetylcholinesterase, butyrylcholinesterase, lipoxygenase, αglucosidase, urease, and reverse transcriptase with some selectivity for acetylcholinesterase, butyrylcholinesterase, and anti-HIV [122]. The reaction proceed smoothly using copper(II) oxide (CuO) powder in neat condition with heating in microwave oven at 80 • C for 15 min, furnishing N(N')-arylbenzamidine derivatives in moderate to good yields, Scheme 63.…”

Section: Scheme 62mentioning

confidence: 99%

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

Baqi

2020

Catalysts

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Cross-coupling reactions furnishing carbon–carbon (C–C) and carbon–heteroatom (C–X) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Ullmann, Ullman–Goldberg, Cadiot–Chodkiewicz, Castro–Stephens, and Corey–House, utilizing elemental copper or its salts as catalyst have, for decades, attracted and inspired scientists. However, these reactions were suffering from the range of functional groups tolerated as well as severely restricted by the harsh reaction conditions often required high temperatures (150–200 °C) for extended reaction time. Enormous efforts have been paid to develop and achieve more sustainable reaction conditions by applying the microwave irradiation. The use of controlled microwave heating dramatically reduces the time required and therefore resulting in increase in the yield as well as the efficiency of the reaction. This review is mainly focuses on the recent advances and applications of copper catalyzed cross-coupling generation of carbon–carbon and carbon–heteroatom bond under microwave technology.

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“…Thus, the planning of synthetic methodologies by heterogeneous catalysis, using easily accessible nanostructured catalysts and microwave-assisted reactions, can contribute significantly for this purpose. In this sense, the combination of CuO nanoparticles and microwave irradiation has been demonstrated an important tool for several catalysed organic reactions (Baqi 2021, Botteselle et al 2012, Dias et al 2018, Taj et al 2019. Thus, according to our interest in studying and preparing simple reactions to obtain organoselenium compounds with biological interest (Doerner et al 2022, Frizon et al 2020, Godoi et al 2012, Moraes et al 2023, Scheide et al 2020), herein we described the mechanistic study of double cross-coupling reaction to enable C-Se and C-N bonds formation for the synthesis of phenoselenazine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and mechanistic study of 2-(trifluoromethyl)-10H-phenoselenazine from double cross coupling reaction

SIQUEIRA,

CIANCALEONI,

SABA

et al. 2024

An. Acad. Bras. Ciênc.

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Phenoselenazines are nitrogen and selenium-based heterocyclic compounds that have important biological activities. However, their preparation methods are scarce and difficult to handle. The synthesis of a phenoselenazine from a simple and robust CuO nanoparticle catalyzed methodology, using bis-aniline-diselenide and 1,2-dihalobenzenes under microwave irradiation. Also, the double-cross-coupling reaction mechanism for C-Se and C-N bond formation, including the observation of a reaction intermediate by mass spectrometry have been studied.

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One-Pot CuO-Catalyzed Green Synthesis of N(N′)-Arylbenzamidines as Potential Enzyme Inhibitors

Cited by 4 publications

References 27 publications

Green by Design: Convergent Synthesis, Computational Analyses, and Activity Evaluation of New FXa Inhibitors Bearing Peptide Triazole Linking Units

Green by Design: Convergent Synthesis, Computational Analyses, and Activity Evaluation of New FXa Inhibitors Bearing Peptide Triazole Linking Units

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

Synthesis and mechanistic study of 2-(trifluoromethyl)-10H-phenoselenazine from double cross coupling reaction

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