Scope and limitations of the synthesis of functionalized quinolizidinones and related compounds by a simple precursor approach via addition of lithium allylmagnesates to 2-pyridones and RCM as key steps

Sośnicki, Jacek G.; Struk, Łukasz; Idzik, Tomasz J.; Maciejewska, Gabriela

doi:10.1016/j.tet.2014.09.043

Cited by 20 publications

(17 citation statements)

References 155 publications

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“…Mp.177–178 °C. 1 H and 13 C NMR spectra matched those previously reported [ 60 ]. 5-(4-Fluorophenyl)pyridin-2(1H)-one [ 60 ] [ 2 ( NH )]: Yield 94%.…”

Section: Appendix A1 Synthesis Of Precursors Of Compounds supporting

confidence: 85%

“…76–77 °C (petroleum ether: ethyl acetate). 1 H and 13 C NMR spectra of 2 matched those previously reported [ 60 ]. 5-(3,4-Difluorophenyl)-2-methoxypyridine ( 3 ): The crude product purified by column chromatography (SiO 2 , n -hexane: ethyl acetate 10:1), gave white solid in 96% yield.…”

Section: Appendix A1 Synthesis Of Precursors Of Compounds supporting

confidence: 82%

“…White solid was filtered off, dissolved in ethyl acetate and passed through a pad of SiO 2 and washed with ethyl acetate till complete product was obtained (TLC-control) [ 1 - 2 ( NH )] or chromatographed on SiO 2 (ethyl acetate) [ 3 - 4 ( NH )], [ 7 - 8 ( NH )]. 5-Phenylpyridin-2(1 H )-one [ 60 ] [ 1 ( NH )]: Yield 84%. Mp.177–178 °C.…”

Section: Appendix A1 Synthesis Of Precursors Of Compounds mentioning

confidence: 99%

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Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1H)-thiones

Perużyńska

Borzyszkowska-Ledwig

Sośnicki

et al. 2021

IJMS

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Most anticancer drugs target mitosis as the most crucial and fragile period of rapidly dividing cancer cells. However the limitations of classical chemotherapeutics drive the search for new more effective and selective compounds. For this purpose structural modifications of the previously characterized pyridine aalog (S1) were incorporated aiming to obtain an antimitotic inhibitor of satisfactory and specific anticancer activity. Structure-activity relationship analysis of the compounds against a panel of cancer cell lines allowed to select a compound with a thiophene ring at C5 of a 3,4-dihydropyridine-2(1H)-thione (S22) with promising antiproliferative activity (IC50 equal 1.71 ± 0.58 µM) and selectivity (SI = 21.09) against melanoma A375 cells. Moreover, all three of the most active compounds from the antiproliferative study, namely S1, S19 and S22 showed better selectivity against A375 cells than reference drug, suggesting their possible lower toxicity and wider therapeutic index. As further study revealed, selected compounds inhibited tubulin polymerization via colchicine binding site in dose dependent manner, leading to aberrant mitotic spindle formation, cell cycle arrest and apoptosis. Summarizing, the current study showed that among obtained mitotic-specific inhibitors analogue with thiophene ring showed the highest antiproliferative activity and selectivity against cancer cells.

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“…Mp.177–178 °C. 1 H and 13 C NMR spectra matched those previously reported [ 60 ]. 5-(4-Fluorophenyl)pyridin-2(1H)-one [ 60 ] [ 2 ( NH )]: Yield 94%.…”

Section: Appendix A1 Synthesis Of Precursors Of Compounds supporting

confidence: 85%

Section: Appendix A1 Synthesis Of Precursors Of Compounds supporting

confidence: 82%

Section: Appendix A1 Synthesis Of Precursors Of Compounds mentioning

confidence: 99%

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Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1H)-thiones

Perużyńska

Borzyszkowska-Ledwig

Sośnicki

et al. 2021

IJMS

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“…The above observations imply that the nucleophilic behaviour of vinylmagnesate 2a , which leads to the addition products, competes with its behaviour as a base, manifested by proton abstraction from the N ‐CH moiety, and enabling self‐addition through the formation of a stabilized anion. The above results show that the behaviour of 2a is in distinct contrast to the reactivity of allyldi‐ n ‐butylmagnesate ( 1a ), which yielded the addition product exclusively in its reactions with the corresponding N ‐allyl‐2‐pyridone (i.e., 3d ) 8d…”

Section: Resultsmentioning

confidence: 89%

Regioselective Synthesis of 6‐Vinyl‐3,6‐dihydropyridine‐2(1H)‐ones through Simple Addition of a Vinylmagnesium “Ate” Complex to 2‐Pyridones

2015

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A highly nucleophilic vinylation reagent, lithium vinyldimethylmagnesate (vinylMe2MgLi), is obtained by mixing vinylmagnesium chloride (1 equiv.) and MeLi (in diethoxymethane; 2 equiv.). The application of this new reagent in the completely regioselective synthesis of 6‐vinyl‐3,6‐dihydro‐1H‐pyridin‐2(1H)‐ones by simple 1,6‐additions to 2‐pyridones is described. Examination of the scope and limitations of the addition revealed the influence on the efficiency of the 6‐vinylation reaction of substituents on the nitrogen atom and on the 2‐pyridone ring.

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“…253) [660]; (11) indoloquinolizinium salts (e.g. 254) [661]; (12) six-and seven-membered ring amines or O-heterocycles fused to a pyranose sugar [662]; (13) six-to eight-membered rings fused to a dihydropyridone ring system and cyclopentenes spiro fused to dihydropyridones [663]; (13) seven-membered ring amine derivatives, including those employed in syntheses of proline-derived dipeptide scaffolds (e.g. 255)…”

Section: )mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

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Scope and limitations of the synthesis of functionalized quinolizidinones and related compounds by a simple precursor approach via addition of lithium allylmagnesates to 2-pyridones and RCM as key steps

Cited by 20 publications

References 155 publications

Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1H)-thiones

Synthesis and Anticancer Activity of Mitotic-Specific 3,4-Dihydropyridine-2(1H)-thiones

Regioselective Synthesis of 6‐Vinyl‐3,6‐dihydropyridine‐2(1H)‐ones through Simple Addition of a Vinylmagnesium “Ate” Complex to 2‐Pyridones

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

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