Fluorinated derivatives of 2-phenyl-3-hydroxy-4(1H)-quinolinone as tubulin polymerization inhibitors

Řehulka, Jiří; Vychodilová, Kristýna; Krejčí, Petr; Gurská, Soňa; Hradil, Pavel; Hajdúch, Marián; Džubák, Petr; Hlaváč, Jan

doi:10.1016/j.ejmech.2020.112176

Cited by 14 publications

(15 citation statements)

References 24 publications

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“… [43] The derivative 2 is derived from the 2‐(4‐fluorophenyl)‐3‐hydroxy‐4(1 H )‐quinolinone with low cytotoxicity against cancer cells. [44] The compound 3 comes from a modification of 2‐(4‐amino‐3,5‐dichlorophenyl)‐3‐hydroxy‐4(1 H )‐quinolinone reported previously as the active derivative against various cancer cell lines. Product 4 was prepared by modification of the 2‐(3‐nitro‐4‐piperid‐1‐ylphenyl)‐3‐hydroxy‐4(1 H )‐quinolinone having significant activity but low selectivity against cancer cell lines.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 1 is derived from 2‐phenyl‐3‐hydroxy‐4(1 H )‐quinolinone reported to have no activity against cancer cells [43] . The derivative 2 is derived from the 2‐(4‐fluorophenyl)‐3‐hydroxy‐4(1 H )‐quinolinone with low cytotoxicity against cancer cells [44] . The compound 3 comes from a modification of 2‐(4‐amino‐3,5‐dichlorophenyl)‐3‐hydroxy‐4(1 H )‐quinolinone reported previously as the active derivative against various cancer cell lines.…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

et al. 2021

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The combination of cytotoxic amino‐BODIPY dye and 2‐phenyl‐3‐hydroxy‐4( 1H )‐quinolinone (3‐HQ) derivatives into one molecule gave rise to selective activity against lymphoblastic or myeloid leukemia and the simultaneous disappearance of the cytotoxicity against normal cells. Both species′ conjugation can be realized via a disulfide linker cleavable in the presence of glutathione characteristic for cancer cells. The cleavage liberating the free amino‐BODIPY dye and 3‐HQ derivative can be monitored by ratiometric fluorescence or by the OFF‐ON effect of the amino‐BODIPY dye. A similar cytotoxic activity is observed when the amino‐BODIPY dye and 3‐HQ derivative are connected through a non‐cleavable maleimide linker. The work reports the synthesis of several conjugates, the study of their cleavage inside cells, and cytotoxic screening.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

et al. 2021

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“…Quinolones are of current interest as anticancer compounds. 27,28 The H 2 O 2 induced CO release reactivity of 6 under illumination conditions is of interest in relation to the role that H 2 O 2 is suggested to have in promoting tumor proliferation. 29 Diketone molecules such as 6 may offer an approach toward reducing H 2 O 2 levels in combination with CO delivery to produce anti-cancer effects.…”

Section: Discussionmentioning

confidence: 99%

Mechanistic studies of visible light-induced CO release from a 3-hydroxybenzo[g]quinolone

et al. 2022

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“…Quinolinones and spiro[4.5]trienones both have been recognized as important heterocyclic skeletons of biologically active molecules. 1 They have been reported to possess diverse pharmacological properties such as anticancer, 2 anti-HCV, 3 anti-inflammatory, 4 and antidiabetic activities. 5 Also, these heterocyclic frameworks can be found in a plethora of biologically active natural compounds.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Wang

Ouyang

et al. 2021

J. Org. Chem.

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A highly substituent-dependent rearrangement allows for the novel and SOCl 2 -induced divergent synthesis of 3-methylthioquinolin-2-ones and 3-methylthiospiro[4.5]trienones through intramolecular electrophilic cyclization of N -aryl propyamides. DMSO acts as both solvent and sulfur source, and use of DMSO- h 6 / d 6 enables the incorporation of SCH 3 or SCD 3 moieties to the 3-position of the heterocyclic framework. Different para -substituents trigger divergent reaction pathways leading to the formation of quinolin-2-ones for mild substituents and spiro[4,5]trienones for both electron-withdrawing and -donating substituents, respectively. On the basis of both computational and experimental results, a new mechanism has been put forward that accounts for the exclusive spirolization/defluorination process and the surprising substituent effects.

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Fluorinated derivatives of 2-phenyl-3-hydroxy-4(1H)-quinolinone as tubulin polymerization inhibitors

Cited by 14 publications

References 24 publications

Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

Mechanistic studies of visible light-induced CO release from a 3-hydroxybenzo[g]quinolone

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

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