Enhanced reactivity of twisted amides inside a molecular cage

Takezawa, Hiroki; Shitozawa, Kosuke; Fujita, Makoto

doi:10.1038/s41557-020-0455-y

Cited by 199 publications

(186 citation statements)

References 28 publications

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“…The mechanism was similar to the strain- induced hydrolysis of peptide bonds in proteins, which biologists have proposed but never examined experimentally. 139 5.1.16. Photodemethylenation of cyclopropanes.…”

Section: Octahedral Msccs (Cage I)mentioning

confidence: 99%

Cavity-based applications of metallo-supramolecular coordination cages (MSCCs)

2020

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Section: Octahedral Msccs (Cage I)mentioning

confidence: 99%

Cavity-based applications of metallo-supramolecular coordination cages (MSCCs)

2020

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“…Since these factors have a pivotal role and affect the reactivity of these ligands. 41,42 In the present study, the strain effect along the MD simulation can be clearly visualized by the overlap of the initial (blue) and representative (red) structures obtained after 10 ns of simulation, as shown in Figure 5. Based on Figure 5, we note that our compounds N-4-Q and N-4-QO showed a slight bending at the quinoline ring (strain), which makes this compound in principle more reactive, resulting in a small oscillation in according to the RMSD graphs ( Figures S4 and S5).…”

Section: Resultsmentioning

confidence: 60%

Nitro derivatives of quinoline and quinoline N-oxide as low-cost alternative for the treatment of SARS-CoV-2 infection

Assis¹,

Castro²,

Jesus

et al. 2020

Preprint

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A new and more aggressive strain of coronavirus, known as SARS-CoV-2, which is highly contagious, has rapidly spread across the planet within a short period of time. Due to its high transmission rate and the significant time–space between infection and manifestation of symptoms, the WHO recently declared this a pandemic. Because of the exponentially growing number of new cases of both infections and deaths, development of new therapeutic options to help fight this pandemic is urgently needed. The target molecules of this study were the nitro derivatives of quinoline and quinoline N-oxide. Computational design at the DFT level, docking studies, and molecular dynamics methods as a well-reasoned strategy will aid in elucidating the fundamental physicochemical properties and molecular functions of a diversity of compounds, directly accelerating the process of discovering new drugs. In this study, we discovered isomers based on the nitro derivatives of quinoline and quinoline N-oxide, which are biologically active compounds and may be low-cost alternatives for the treatment of infections induced by SARS-CoV-2.

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“…An impressive nanoconfinement effect on the classical reactivity of amide derivatives was reported by the same group [26] . The encapsulation of amides 4 and 7 (Scheme 2) in the Pt‐cage 3 b , induces a mechanical twisting of the amide bond (Scheme 3), that adopts a cis ‐twisted conformation stabilized by the cavity of 3 b .…”

Section: Supramolecular Catalysis In Confined Spacementioning

confidence: 81%

Supramolecular Catalysis with Self‐Assembled Capsules and Cages: What Happens in Confined Spaces

et al. 2020

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The confined space inside self‐assembled capsules or cages provides a unique environment in which organic reactions can be efficiently catalyzed, thanks to the confinement effect of the substrates. In confined spaces the chemical reactions can show unusual mechanisms due to the conformational control of the substrates, steric constrictions, stabilization of species by secondary interactions, and solvent exclusion. Consequently, the classical rules of the organic reactivity are often broken. Thus, many examples reported to data in the literature confirm the paradigm stated by D. J. Cram in 1989: “These carceplexes represent a new state of matter whose interiors are new phase…”. The confined space inside the self‐assembled capsules or cages represents a new phase for the chemical reactivity where there is still so much to explore. In this review we highlight the best‐known cases of reactivity in confined spaces, focusing our attention on the driving forces that drive the encapsulated reactions toward uncommon outcomes. Literature examples that constitute the landmarks in the topic of supramolecular catalysis in confined spaces are also reviewed.

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Enhanced reactivity of twisted amides inside a molecular cage

Cited by 199 publications

References 28 publications

Cavity-based applications of metallo-supramolecular coordination cages (MSCCs)

Cavity-based applications of metallo-supramolecular coordination cages (MSCCs)

Nitro derivatives of quinoline and quinoline N-oxide as low-cost alternative for the treatment of SARS-CoV-2 infection

Supramolecular Catalysis with Self‐Assembled Capsules and Cages: What Happens in Confined Spaces

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