N-phosphorylated 3,5-bis(arylidene)4-piperidones: Synthesis, X-ray structure, and evaluation of antitumor activity

Odinets, Irina L.; Аrtyushin, О. I.; Goryunov, E. I.; Rybalkina, Ekaterina Yu.; Kosilkin, Ilya V.; Timofeeva, Tatiana V.; Antipin, M. Yu.

doi:10.1002/hc.20147

Cited by 24 publications

(15 citation statements)

References 12 publications

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“…Both olefinic bonds have E configuration, which is in agreement with the results obtained earlier for similar compounds [6,7,8,[11][12][13][14][15]. Taking into consideration the general similarity of the spectral data we also assigned the structures of compounds 4a-c to E,E-isomers.…”

Section: Experimental Part)supporting

confidence: 86%

“…Recent observations demonstrated fluorescent properties of some representatives of 3,5-bis(arylidene)-4-piperidones [7][8][9]. Natural fluorescence in the case of cytotoxic materials might be very helpful in tracking of their cellular pathway.…”

Section: Recentlymentioning

confidence: 98%

“…Therefore, we may mention the clear tendency: formation of piperidonium structures 5a-e 6a-e Table 2 In vitro growth inhibition concentrations (IC 50 ) of the testedcompounds against A549 tumor cell line result in increase of the biological activity in a series of bis(3,5-arylidene)piperidin-4-ones. As mentioned above, the presence of conjugated bonds system results in fluorescent properties of 3,5-bis-(arylidene)piperid-4-one derivatives (two-photon absorption) [7][8][9]. Fluorescent properties of the compounds obtained allowed one to estimate their distribution in cancer cells and such experiment was performed using compound 6b as a representative example.…”

Section: Experimental Part)mentioning

confidence: 99%

“…Scheme 1) [7]. Both acylated and phosphorylated compounds may be considered as pro-drugs giving the parent NH-compound via hydrolysis in vivo under the action of the suitable enzymes.…”

Section: Recentlymentioning

confidence: 99%

“…Anticancer agent Melphalan (Sarcolysin) was used as a positive control similar to assays of cytotoxic properties of other 3,5-bis(arylidene)-4-piperidone derivatives described in literature [1][2][3][4][5][6][7]. It should be noted that the activity of some analogues of compounds 6 against non-resistant murine tumor cell lines was reported in ref.…”

Section: Experimental Part)mentioning

confidence: 99%

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N‐alkylated 3,5‐bis(arylidene)‐4‐piperidones. Synthetic approaches, X‐ray structure and anticancer activity

Makarov

Odinets

Lyssenko

et al. 2008

Journal of Heterocyclic Chem

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In a search for cytotoxic fluorescent materials a series of N-alkylated and N,N-dialkylated 3,5-bis(arylidene)piperidones was synthesized. Alkylation of 3,5-bis(arylidene)-4-piperidone afforded quaternary salts only while condensation of N-alkyl-4-piperidones with substituted benzaldehydes was a convenient route to the corresponding N-alkylated compounds. Compounds and their pharmaceutically acceptable salts demonstrated high activity against resistant human lung carcinoma cell line A549 with IC 50 values in the range of 0.3-6.5 µM.

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Section: Experimental Part)supporting

confidence: 86%

Section: Recentlymentioning

confidence: 98%

Section: Experimental Part)mentioning

confidence: 99%

“…Scheme 1) [7]. Both acylated and phosphorylated compounds may be considered as pro-drugs giving the parent NH-compound via hydrolysis in vivo under the action of the suitable enzymes.…”

Section: Recentlymentioning

confidence: 99%

Section: Experimental Part)mentioning

confidence: 99%

See 3 more Smart Citations

N‐alkylated 3,5‐bis(arylidene)‐4‐piperidones. Synthetic approaches, X‐ray structure and anticancer activity

Makarov

Odinets

Lyssenko

et al. 2008

Journal of Heterocyclic Chem

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Methylenebisphosphonates with Dienone Pharmacophore: Synthesis, Structure, Antitumor and Fluorescent Properties

Makarov

Leonova

Rybalkina³

et al. 2012

Archiv der Pharmazie

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The synthesis and the antitumor activity and fluorescent properties screening of novel bisphosphonate conjugates with cytotoxic 3,5-bis((hetero)arylidene)-4-piperidone residues were performed. The facile and rapid synthetic route was based on the aza-Michael addition of NH-3,5-bis((hetero)arylidene)-4-piperidones to tetraethyl ethylidenebisphosphonate. The synthesized compounds displayed high inhibitory properties towards Caov3, A549, PC3, and KB 3-1 human carcinoma cell lines. Among those, compounds bearing 4-cyano-phenyl and 3-pyridinyl substituents were revealed as the most active drug candidates with IC(50) values in the range of 0.5-2.5 µM. Methylenebisphosphonate with 4-Me(2) N-C(6) H(4) groups in the piperidone framework possessing fluorescence properties may be of interest for visualization of BPs skeletal distribution and cellular uptake in bones and other tissues.

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3,5‐Bis(benzylidene)‐4‐oxo‐1‐phosphonopiperidines and Related Diethyl Esters: Potent Cytotoxins with Multi‐Drug‐Resistance Reverting Properties

Das

Selvakumar

et al. 2009

ChemMedChem

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A series of 3,5-bis(benzylidene)-4-piperidones 3 were converted into the corresponding 3,5-bis(benzylidene)-1-phosphono-4-piperidones 5 via diethyl esters 4. The analogues in series 4 and 5 displayed marked growth inhibitory properties toward human Molt 4/C8 and CEM Tlymphocytes as well as murine leukemia L1210 cells. In general, the N-phosphono compounds 5, which are more hydrophilic than the analogues in series 3 and 4, were the most potent cluster of cytotoxins, and, in particular, 3,5-bis-(2-nitrobenzylidene)-1-phosphono-4-piperidone 5g had an average IC 50 value of 34 nM toward the two T-lymphocyte cell lines. Four of the compounds displayed potent cytotoxicity toward a panel of nearly 60 human tumor cell lines, and nanomolar IC 50 values were observed in a number of cases. The mode of action of 5g includes the induction of apoptosis and inhibition of cellular respiration. Most of the members of series 4 as well as several analogues in series 5 are potent multi-drug resistance (MDR) reverting compounds. Various correlations were noted between certain molecular features of series 4 and 5 and cytotoxic properties, affording some guidelines in expanding this study.

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N-phosphorylated 3,5-bis(arylidene)4-piperidones: Synthesis, X-ray structure, and evaluation of antitumor activity

Cited by 24 publications

References 12 publications

N‐alkylated 3,5‐bis(arylidene)‐4‐piperidones. Synthetic approaches, X‐ray structure and anticancer activity

N‐alkylated 3,5‐bis(arylidene)‐4‐piperidones. Synthetic approaches, X‐ray structure and anticancer activity

Methylenebisphosphonates with Dienone Pharmacophore: Synthesis, Structure, Antitumor and Fluorescent Properties

3,5‐Bis(benzylidene)‐4‐oxo‐1‐phosphonopiperidines and Related Diethyl Esters: Potent Cytotoxins with Multi‐Drug‐Resistance Reverting Properties

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