Synthesis of Isonitrile Derivatives of Diglycerides and Carbohydrates as Intermediates for Multicomponent Ugi Reaction

Nichugovskiy, Artemiy; Khrulev, A. A.; Perevoshchikova, K. A.; Cheshkov, Dmitry A.; Морозова, Н. Г.; Маслов, М. А.

doi:10.1134/s1068162021040166

Cited by 3 publications

(3 citation statements)

References 30 publications

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“…Quantum transitions between these states lead to an effective spin-spin interaction between carbon and nitrogen, resulting in the splitting of carbon signals into three lines with an intensity ratio of 1:1:1. However, in some cases, due to the low concentration of isonitriles, this effect may be weak or not observed at all [14,15]. In the 13 C NMR spectrum, CH2-NC is a singlet at 69.16 ppm.…”

Section: Resultsmentioning

confidence: 99%

1-(3-Isoselenocyanatopropyl)adamantane

Pitushkin

Burmistrov

Бутов

2023

Molbank

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Section: Resultsmentioning

confidence: 99%

1-(3-Isoselenocyanatopropyl)adamantane

Pitushkin

Burmistrov

Бутов

2023

Molbank

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“…On the second step, the reduction of amide groups is carried out followed by the removal of protective groups. In this work, the commercially available tert -butyl isocyanide ( 7a ) or the previously obtained octadecyl isocyanide ( 7b ) [ 18 ] were used as isonitrile components, glacial acetic acid ( 8a ) or N -acetylglycine ( 8b ) as the carboxyl component, and N , N ’-dibenzylalkanediamine ( 9a – c ) as the diamine component, while paraformaldehyde ( 10 ) was used as the carbonyl component. The reaction was refluxed in methanol in an equimolar ratio of starting reagents for 16 h ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…2-Hydroxymethylbenzoic acid ( 8c ) was prepared as described previously [ 29 ]. The synthesis of isonitrile derivatives both of diglyceride ( 7c ) and D-glucose was performed according to [ 18 ]. The synthesis of PhSiH 3 was described in reference [ 38 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

Nichugovskiy

Maksimova²,

Trapeznikova

et al. 2022

Molecules

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Natural polyamines (PAs) are involved in the processes of proliferation and differentiation of cancer cells. Lipophilic synthetic polyamines (LPAs) induce the cell death of various cancer cell lines. In the current paper, we have demonstrated a new method for synthesis of LPAs via the multicomponent Ugi reaction and subsequent reduction of amide groups by PhSiH3. The anticancer activity of the obtained compounds was evaluated in the A‑549, MCF7, and HCT116 cancer cell lines. For the first time, it was shown that the anticancer activity of LPAs with piperazine fragments is comparable with that of aliphatic LPAs. The presence of a diglyceride fragment in the structure of LPAs appears to be a key factor for the manifestation of high anticancer activity. The findings of the study strongly support further research in the field of LPAs and their derivatives.

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One-Pot Multicomponent Reactions in Deep Eutectic Solvents

Demirbaş

Ayvaz

Demirbas

et al. 2023

COC

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The increasing environmental pollution and its detrimental impact on the ecosystem made scientists develop new chemical strategies involving eco-friendly chemicals, solvents, catalysts, atom-economical procedures, and alternative energy sources. Among these, deep eutectic solvents (DESs) are primarily low-melting mixtures of quaternary ammonium salt and hydrogen-bond acceptors. Low toxicity, easy preparation, low cost, biodegradability, low vapor pressure, and recyclability are the main advantages of DESs. Multicomponent reactions (MCRs) are efficient procedures for generating new libraries with high structural complexity. MCRs can give one product from at least three components in a single operation with high bond-forming efficiency, shortness, and structural diversity. Compared with conventional methodologies, the structural diversity, the convergent and atom economic character, the easy applicability of a one-pot operation, the accessibility to complex molecules, the minimized waste formation, and high selectivity are the main advantages of one-pot multicomponent reactions. The application of MCRs in eutectic solvents not only simplifies procedures but also displays more positive effects on the protection of the ecosystem.

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Synthesis of Isonitrile Derivatives of Diglycerides and Carbohydrates as Intermediates for Multicomponent Ugi Reaction

Cited by 3 publications

References 30 publications

1-(3-Isoselenocyanatopropyl)adamantane

1-(3-Isoselenocyanatopropyl)adamantane

Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity

One-Pot Multicomponent Reactions in Deep Eutectic Solvents

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