Cytotoxicity of new n-butylamino and sulfur-containing derivatives of polyfluorinated 1,4-naphthoquinone

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

“…Quinones are important compounds widely spread in Nature. Compounds containing 1,4-naphthoquinone moiety exhibit a broad spectrum of biological activities such as cytotoxic [ 1 , 2 ] antiviral [ 3 , 4 ] anti-inflammatory [ 5 , 6 ] antimalarial [ 7 ], antibacterial [ 8 , 9 ], antifungal [ 10 ] and antiproliferative properties [ 11 ]. Naphthoquinones are particularly important in dye chemistry, and recently they have been used for new infrared dyes in optical recording media [ 12 , 13 , 14 ].…”

Cytotoxicity of new polyfluorinated 1,4-naphtoquinones with diverse substituents in the quinone moiety

“…Compound 1 inhibited the growth of LMTK (11.7 lM) and PMF (3.3 lM) cells at concentrations 2.8-9.8-fold higher than the growth of RPMI cells, while its effects on normal cells were comparable with that on MCF-7 cells (5.8 lM) (Table 1). Compound 4 inhibited the growth of LMTK cells by 50% at 30 lM, whereas the growth of PMF cells was suppressed only by 45% at significantly higher concentrations (25 lg/ml or 75.0 lM) ( Table 1) 15,16 The structures of 1-8 resemble that of F-Cpd5 and above mentioned naphtoquinones (I-VII), therefore one could expect similar effects of all these compounds on the Cdc25 phosphatases and growth of tumor cells. For RPMI cancer cells, F-Cpd5 revealed IC 50 2.1-14.8-fold higher than IC 50 of compounds 1-8, while all compounds 1-5 inhibited the growth of MCF cells 13-72-fold better than F-Cpd5 (Table 1).…”

“…The location and multiplicities of the F 5 -F 8 signals of quinone 6: d/ppm 23.8 (dt, F 8 , J 8,5 , J 8, 6 12 Hz, J 8,7 = 19.0 Hz), 22.4 (ddd, F 5 , J 5, 6 19 Hz, J 5,7 10 Hz, J 5,8 -12.5 Hz), 16.7 (dt, F 6 , J 6,5 , J 6,7 19 Hz, J 6,8 = 11.2 Hz), 14.6 (dt, F 7 , J 7,6 , J 7, 8 19 Hz, J 7,5 = 9.9 Hz) are close to those of 2-n-butylaminopentafluoro-1,4-naphthoquinone (11): d/ppm 25.8 (dt, F 8 , J 8,5 , J 8, 6 12 Hz, J 8,7 20 Hz), 24.2 (ddd, F 5 , J 5,6 20 Hz, J 5,7 10 Hz, J 5, 8 12 Hz), 19.8 (ddt, F 6 , J 6,5 , J 6,7 20 Hz, J 6,3 = 4.5 Hz), 15.0 (dt, F 7 , J 7,5 10 Hz, J 7,6 , J 7,8 20 Hz). 15 The obvious main difference between the 19 F NMR spectra of 6 and 11 is an absence of the F 3 -F 6 spin coupling in the case of 6.…”

“…15,16 Interestingly, several new polyfluorinated n-alkylamino-, phenylamino-, and alkylthioderivatives of 1,4-naphthoquinone suppressed the growth of cancer cells at significantly lower concentrations than normal cells and antioxidant and mutagenic properties in the bacterial system significantly depend upon nature of the functional groups, only 3-4 of them possessing a highly promising combination of these properties. 15,16 Thus, it seems reasonable to suggest that this approach may be more rational for searching new inhibitors of Cdc25 phosphatases and tumor cell growth without side effects.…”

Reactions of Sulfenyl Chlorides of Substituted 1,4-Naphthoquinone

“…Many derivatives of 1,4-naphthoquinone exhibit antibacterial, fungicidal, and insecticidal activity. Derivatives of 1,4-naphthoquinone with antiviral, antiphthisic, antibiotic, and antimalarial action were found among them and can be used for pharmacological treatment of different types of respiratory diseases [1][2][3][4][5][6][7][8][9]. Preparations on the basis of 1,4-naphthoquinone derivatives are effectively used for the treatment of brain function disorders (cerebral infarction, cerebral hemorrhage, atherosclerosis), and also have high antioxidant, cytolytic and cytostatic activity [10].…”