Six-Membered Heterocycles

Ram, Vishnu Ji; Sethi, A. S.; Nath, Mahendra; Pratap, Ramendra

doi:10.1016/b978-0-12-819210-8.00002-3

Cited by 16 publications

(5 citation statements)

References 1,066 publications

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“…It is known that 1,3-dioxanes-very attractive heteroanalogs of cyclohexane-belong to the classical objects of conformational analysis [94]. Besides that, due to their wide range of pharmacological action, they may be used for the creation of new drugs [205,206] and also as reagents in fine organic synthesis [207][208][209][210][211]. All this makes it relevant to consider the conformational properties of these compounds inside nanotubes, from the perspectives of nanoreactors [68][69][70][71][72][73][74][75] and drug delivery systems [15,19].…”

Section: 3-dioxane In Nanotubesmentioning

confidence: 99%

Stereochemistry of Simple Molecules inside Nanotubes and Fullerenes: Unusual Behavior of Usual Systems

Кузнецов

2020

Molecules

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Over the past three decades, carbon nanotubes and fullerenes have become remarkable objects for starting the implementation of new models and technologies in different branches of science. To a great extent, this is defined by the unique electronic and spatial properties of nanocavities due to the ramified π-electron systems. This provides an opportunity for the formation of endohedral complexes containing non-covalently bonded atoms or molecules inside fullerenes and nanotubes. The guest species are exposed to the force field of the nanocavity, which can be described as a combination of electronic and steric requirements. Its action significantly changes conformational properties of even relatively simple molecules, including ethane and its analogs, as well as compounds with C−O, C−S, B−B, B−O, B−N, N−N, Al−Al, Si−Si and Ge−Ge bonds. Besides that, the cavity of the host molecule dramatically alters the stereochemical characteristics of cyclic and heterocyclic systems, affects the energy of pyramidal nitrogen inversion in amines, changes the relative stability of cis and trans isomers and, in the case of chiral nanotubes, strongly influences the properties of R- and S-enantiomers. The present review aims at primary compilation of such unusual stereochemical effects and initial evaluation of the nature of the force field inside nanotubes and fullerenes.

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Section: 3-dioxane In Nanotubesmentioning

confidence: 99%

Stereochemistry of Simple Molecules inside Nanotubes and Fullerenes: Unusual Behavior of Usual Systems

Кузнецов

2020

Molecules

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“…Therefore, the development of metal-free, convenient, efficient, and environmentally friendly protocols by using readily available hydrogen sources as hydrogen donors is a key scientific issue in the field of TH research. As the most abundant, piperidine as an inexpensive and readily available organic reagent often plays the role of the base and ligands in most organic reactions but has not been used as a hydrogen donor in TH under the electrochemical conditions …”

mentioning

confidence: 99%

Electrochemical-Induced Transfer Hydrogenation of Imidazopyridines with Secondary Amine as Hydrogen Donor

et al. 2020

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Electrochemical-induced transfer hydrogenation (TH) of N-heteroaromatic to construct biologically active functional molecule is an appealing and yet challenging task. We report herein the first selective transfer hydrogenation of imidazopyridine derivatives with secondary amines as the hydrogen donors under electrochemical conditions. The successful conversion of cathode transfer hydrogenation depends on the solvation effect. Importantly, such electrochemical-induced transfer hydrogenation can be easily amplified with excellent efficiency.

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“…Benzo[f ]quinoline is a polynuclear azaheterocycle with an extended π-π conjugation of potential interest in medicine, opto-electronics, agriculture, etc. [1,2]. Although the native heterocycle is known to be an environmental pollutant [3,4] and has been detected in coal tar [5], petroleum distillate [6], and urban air particles with genetic effects [2,7], recent research has shown that incorporating the benzo[f ]quinoline skeleton into the design of certain compounds can be advantageous, resulting in new derivatives with biological properties such as antimicrobial [8][9][10] and anticancer activity [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity

Oniciuc

Mantu

Diaconu

et al. 2023

IJMS

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This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[f]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition reaction. The synthesized compounds were characterized by FTIR, NMR, and X-ray diffraction on monocrystals in the case of compounds 6c and 7c. An in vitro single-dose anticancer assay of eighteen benzo[f]quinoline compounds, quaternary salts, and cycloadducts was performed. The results showed that the most active compounds were quaternary salts 3d and 3f with aromatic R substituents. Quaternary salt 3d revealed non-selective activity against all types of cancer cells, while salt 3f exhibited highly selective activity against leukemia cells. Compound 3d also presented remarkable cytotoxic efficiency against four distinct types of cancer cells—namely, non-small cell lung cancer HOP-92, melanoma LOX IMVI, melanoma SK-MEL-5, and breast cancer MDA-MB-468. The study also includes SAR correlations.

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Six-Membered Heterocycles

Cited by 16 publications

References 1,066 publications

Stereochemistry of Simple Molecules inside Nanotubes and Fullerenes: Unusual Behavior of Usual Systems

Stereochemistry of Simple Molecules inside Nanotubes and Fullerenes: Unusual Behavior of Usual Systems

Electrochemical-Induced Transfer Hydrogenation of Imidazopyridines with Secondary Amine as Hydrogen Donor

Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity

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