Novel π-conjugated systems based on pyrimidine N-Oxide. (May 2019)

• Record Type: Journal Article
• Authors: Sedenkova, Kseniya N.; Kolodyazhnaya, Julia V.; Vasilenko, Dmitry A.; Gracheva, Yulia A.; Kharitonoshvili, Elena V.; Grishin, Yuri K.; Chistov, Alexey A.; Rybakov, Victor B.; Holt, Tina; Kutateladze, Andrei G.; Kuznetsova, Tamara S.; Milaeva, Elena R.; Averina, Elena B.
• Is Part Of: Dyes and pigments. Volume 164(2019)
• Page Start: 72
• Page End: 81
• Publication Date: 2019-05
• Subjects: Pyrimidines -- π-Conjugated systems -- Knoevenagel condensation -- Fluorescence -- Metal cations -- Anticancer activity; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.12.067
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Pyrimidine N -oxide moiety for the first time was used as a heterocyclic core for the construction of π-conjugated molecules with fluorescent properties. For the synthesis of the title compounds a simple two-step protocol starting from readily available 4-fluoro-2-methylpyrimidine N -oxides was elaborated. A series of 17 novel pyrimidine N -oxide derivatives containing various functional substituents and π-conjugated systems of different length were obtained. The title compounds revealed fluorescent properties in visible region, possessing emission maximum up to 575 nm. Deoxygenation of the N -oxide group led to the loss of visible fluorescence. The chemosensor properties towards TFA and a number of metal cations were demonstrated for3a, the first representative of the title series. Cytotoxic activity against breast adenocarcinoma cell line was found for three pyrimidine N -oxide derivatives3b, i, n . Pyrimidine N -oxide3a was shown to possess excellent biocompatibility and capability to enter cells, that makes it a promising structure for development of bioimaging fluorescent probes. Highlights: The first series of π-conjugated systems based on pyrimidine N -oxide was obtained. The title compounds display fluorescence in visible region and chemosensor properties. Pyrimidine N -oxide3a is non-toxic and readily accumulates in cells. Three pyrimidine N -oxides display cytotoxicity against human cancer cells.