Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Niedballa, Jonas; Müller, Thomas J. J.

doi:10.3390/catal12010090

Cited by 13 publications

(3 citation statements)

References 95 publications

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“…In recent years, numerous attempts have been made toward the synthesis of 1,5-benzodiazepines from available nitrogen sources, under mild reaction conditions, and more facile operational procedures, including a multicomponent reaction strategy [ 43 , 44 , 45 ]. It was known that 1,3-diarylprop-2-yn-1-ones were reactive towards cyclocondensation with binucleophiles, including benzene-1,2-diamines [ 43 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Pharmacological Evaluation, and Molecular Modeling of Lappaconitine–1,5-Benzodiazepine Hybrids

et al. 2023

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Diterpenoid alkaloids, originating from the amination of natural tetracyclic diterpenes, have long interested scientists due to their medicinal uses and infamous toxicity which has limited the clinical application of the native compound. Alkaloid lappaconitine extracted from various Aconitum and Delphinium species has displayed extensive bioactivities and active ongoing research to reduce its adverse effects. A convenient route to construct hybrid molecules containing diterpenoid alkaloid lappaconitine and 3H-1,5-benzodiazepine fragments was proposed. The key stage involved the formation of 5′-alkynone-lappaconitines in situ by acyl Sonogashira coupling of 5′-ethynyllappaconitine, followed by cyclocondensation with o-phenylenediamine. New hybrid compounds showed low toxicity and outstanding analgesic activity in experimental pain models, which depended on the nature of the substituent in the benzodiazepine nucleus. An analogous dependence was also shown for the antiarrhythmic activity in the epinephrine arrhythmia test in vivo. Studies on the isolated atrium have shown that the mechanism of action of the new compounds is included the blockade of beta-adrenergic receptors and potassium channels. Molecular docking analysis was conducted to determine the binding potential of target molecules with the voltage-gated sodium channel NaV1.5. All obtained results provide a basis for future rational modifications of lappaconitine, reducing side effects, while retaining its therapeutic effects.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Pharmacological Evaluation, and Molecular Modeling of Lappaconitine–1,5-Benzodiazepine Hybrids

et al. 2023

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“…[14] Actually, it is possible to find reviews of almost every aspects of MCRs. [15][16][17][18][19][20][21] However, despite the huge development of MCRs, in particular in the last two decades, much is still to be learned.…”

Section: Introductionmentioning

confidence: 99%

“…Some traditional MCRs, which have been known for more than a century, still have their reaction mechanisms hotly debated [14] . Actually, it is possible to find reviews of almost every aspects of MCRs [15–21] . However, despite the huge development of MCRs, in particular in the last two decades, much is still to be learned.…”

Section: Introductionmentioning

confidence: 99%

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

2022

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In the current Perspective article, we critically review and discuss the importance of solvent effects on multicomponent reactions, likely the most neglected aspect in this research field. Although solvent-free reactions may be desirable sometimes, most multicomponent reactions still require a solvent to properly promote them. This requirement makes the knowledge of all drawbacks and advantages of each solvent a central issue when trying to optimize multicomponent reactions. Yet, only a few studies with actual evidence of solvent effects on these key reactions have been published. For the quantitative effects of solvents, studies are even scarcer. In this Perspective, we argue that greater efforts should be directed to such fundamental studies.

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Ruthenium‐Catalyzed C−C Coupling of Terminal Alkynes with Primary Alcohols or Aldehydes: α,β‐Acetylenic Ketones (Ynones) via Oxidative Alkynylation

et al. 2023

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Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Cited by 13 publications

References 95 publications

Synthesis, Pharmacological Evaluation, and Molecular Modeling of Lappaconitine–1,5-Benzodiazepine Hybrids

Synthesis, Pharmacological Evaluation, and Molecular Modeling of Lappaconitine–1,5-Benzodiazepine Hybrids

Solvent Screening Is Not Solvent Effect: A Review on the Most Neglected Aspect of Multicomponent Reactions

Ruthenium‐Catalyzed C−C Coupling of Terminal Alkynes with Primary Alcohols or Aldehydes: α,β‐Acetylenic Ketones (Ynones) via Oxidative Alkynylation

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