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Проведено реакції нуклеофільного заміщення між 5-R-2,3-дихлоро-1,4-нафтохінонами і 4-аміно-5-гетерил- 4H-1,2,4-триазол-3-тіолами. Показано, що взаємодія може відбуватися за двома альтернативними напрямами, які регулюються за допомогою умов реакції. Проведено пошук відмінностей в реагуючих атомах досліджуваних молекул внаслідок порівняння розрахованих індексів Фукуї. Експери- ментально показано вплив електронодонорних та електроноакцепторних замісників у 5 положенні 2,3-дихлор- 1,4-нафтохінону на регіоселективність перебігу реакції нуклеофільного заміщення. Порівняння отриманих спектрів 1H ЯМР з DFT розрахованими для обох можливих форм одержуваних продуктів дає можливість однозначно віднести синтезовані сполуки відповідним структурам. Синтезовані сполуки охарактеризовані за допомогою ІЧ, 1H ЯМР, 13C ЯМР спектроскопії та елементного аналізу. Reactions of nucleophilic substitution between 5-R-2,3-dichloro-1,4-naphthoquinones and 4-amino-5- heteryl-4H-1,2,4-triazoles-3-thiols were carried out. It is shown that the interaction can take place in two alternative ways and the reaction direction is controlled by reaction conditions. Search of differences in atoms reactivity in investigated molecules by comparing the calculated Fukui atonic indices was conducted. The influence of electron donor and electron acceptor substituent in 2,3-dichloro- 1,4-naphthoquinone 5th position on the nucleophilic substitution reaction regioselectivity was shown experimentally. Comparison of obtained 1H NMR spectra with DFT calculated for both possible isomers of obtained products allowed to uniquely attribute synthesized compounds to relevant structures. The synthesized compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.

Novel thiopyrano[2,3-d]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5H)furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5H)furanone was studied by DFT at the M06-2X/6-31+G(d,p) level. The stereo- and regioselectivities of cycloaddition were confirmed by NMR spectra and single-crystal X-ray diffraction analyses.

Novel thiopyrano[2,3-d]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5H)furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5H)furanone was studied by DFT at the M06-2X/6-31+G(d,p) level. The stereo- and regioselectivities of cycloaddition were confirmed by NMR spectra and single-crystal X-ray diffraction analyses.

International audience; Thiosulfonate derivatives based on quinones were synthesized for studying "structure-activity relationship" compounds with an acylated and a free amino-group. Anti-platelet activity of the synthesized compounds was determined and the influence of substituents on the activity of the derivatives was assessed.

The screening of the in vitro anticancer activity of the synthesized compounds shows that compounds (IVa), (VIIIb), (VIIId) are the most active compounds against different cell lines.