Salts of spiro-derivatives of benzo[f]quinoline and several natural carboxylic acids

Дикусар, Е. А.; Kadutskii, A. P.; Козлов, Н. Г.; Yuvchenko, A. P.; Mel’nichuk, L. A.

doi:10.1007/s10600-006-0055-0

Cited by 3 publications

(3 citation statements)

References 2 publications

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“…[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]. Additionally, some derivatives have been designed and synthesized based on the fluorescent properties of benzo[f ]quinoline [14,15], and some of these derivatives have been shown to have potential for use in organic light-emitting devices (OLED) [16][17][18][19].…”

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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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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“…The polynuclear azaheterocycle benzo[ c ]quinoline has potential applications in optoelectronics, agriculture, and other fields [ 1 , 2 ]. Recent studies have shown that incorporating the benzoquinoline skeleton into the design of some compounds can be advantageous, leading to new derivatives with biological properties such as antimicrobial [ 3 , 4 ] and anticancer activity [ 5 , 6 , 7 ]. This is true even though the native heterocycle is known to be an environmental pollutant [ 8 , 9 ] and has been detected in coal tar [ 10 , 11 ], petroleum distillate [ 12 ], and urban air particles with genetic effects [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

The Effective Synthesis of New Benzoquinoline Derivatives as Small Molecules with Anticancer Activity

Zbancioc,

Mangalagiu,

Moldoveanu

2023

Pharmaceuticals

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In this study, some novel benzo[c]quinoline derivatives were synthesized, their structural characteristics were described, and their in vitro anticancer efficacy was investigated. The synthesis involves an initial quaternization of the nitrogen atom from benzo[c]quinoline and then a [3+2] dipolar cycloaddition reaction of the in situ formed ylide. The effectiveness of synthesis using traditional thermal heating (TH) compared to microwave (MW) and ultrasound (US) irradiation was investigated in detail. The setup of a reaction under MW or US irradiation offers a number of additional benefits: higher yields, a reduction in the amount of solvent used compared to TH, a reduction in the reaction time from hours to minutes, and a reduction in the amount of energy consumed. The structure of all the obtained compounds was proved by several spectral techniques (FTIR, HRMS, and NMR). All benzo[c]quinoline derivatives (quaternary salts and cycloadducts) along with ten other benzo[f]quinoline derivatives (quaternary salts and cycloadducts), previously obtained, were tested in an in vitro single-dose anticancer experiment. The results demonstrated that the cycloadducts 5a–c and 6a–c exhibit stronger anticancer activity than quaternary salts 3a–c. The most active compound is compound 5a, with anticancer activity on most of the cell lines studied, while the second most active compound is 6c, showing significant lethality for the SR leukemia cell line (17%). Structure-activity relationship (SAR) correlations are also included in the study.

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“…The optimum ratios of the reagents in relation to the structure of the acid were selected. The yields of the salts amounted to 91-96%[110…”

mentioning

confidence: 99%

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Козлов¹,

Gusak²,

Kadutskii³

2010

Chem Heterocycl Comp

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Salts of spiro-derivatives of benzo[f]quinoline and several natural carboxylic acids

Cited by 3 publications

References 2 publications

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

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

The Effective Synthesis of New Benzoquinoline Derivatives as Small Molecules with Anticancer Activity

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

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