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Pregled bibliografske jedinice broj: 579062

Časopis

Autori: Veljković, Jelena; Uzelac, Lidija; Molčanov, Krešimir; Mlinarić-Majerski, Kata; Kralj, Marijeta; Wan, Peter; Basarić, Nikola
Naslov: Sterically Congested Adamantylnaphthalene Quinone Methides
Izvornik: Journal of organic chemistry (0022-3263) 77 (2012), 10; 4596-4610
Vrsta rada: članak
Ključne riječi: adamantanes ; antiproliferative activity ; laser flash photolysis ; naphthols ; photodehydroxylation ; proton transfer ; quinone methides
Sažetak:
Five new (2-adamantyl)naphthol derivatives (5-9, quinone methide precursors, QMP) were synthesized and their photochemical reactivity investigated by preparative photolyses, fluorescence spectroscopy and laser flash photolysis (LFP). Excitation of QMP 5 to S1 leads to efficient excited state intramolecular proton transfer (ESIPT) coupled with dehydration, giving quinone methide QM5 which was characterized by LFP (in CH3CN-H2O, λmax = 370 nm, τ =0.19 ms). On irradiation of QMP 5 in CH3OH-H2O (4:1), the quantum yield of methanolysis is Φ = 0.70. Excitation of naphthols QMP 6-8 to S1 in CH3CN leads to photoionization and formation of naphthoxyl radicals. In a protic solvent QMP 6-8 undergo solvent-assisted PT giving QM6 or zwitterion QM8 that react with nucleophiles delivering adducts, but with a significantly lower quantum efficiency. QMP 9 in a protic solvent undergoes two competitive processes, photosolvolysis via QM9 and solvent-assisted PT to carbon atom of the naphthalene giving zwitterion. QM9 has been characterized by LFP (in CH3CN-H2O, λmax > 600 nm, τ =0.9 ms). In addition to photogenerated QMs, two stable naphthalene QMs QM10 and QM11 were synthesized thermally and characterized by X-ray crystallography. QM10 and QM11 do not react with H2O but undergo acid-catalyzed fragmentation or rearrangement. Antiproliferative activity of 5-9 was investigated on three human cancer cell lines. Exposure of MCF-7 cells treated with 5 to 300 nm irradiation leads to enhanced antiproliferative effect, in accordance with the activity being due to the formation of QM5.
Projekt / tema: HRZZ-UIP-02.05/25, 098-0982933-2911
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Temeljne medicinske znanosti
URL Internet adrese: http://pubs.acs.org/doi/abs/10.1021/jo3002479
http://dx.doi.org/10.1021/jo3002479
Broj citata:
Altmetric:
DOI: 10.1021/jo3002479
URL cjelovitog teksta:
Google Scholar: Sterically Congested Adamantylnaphthalene Quinone Methides
Upisao u CROSBI: eluksa@irb.hr (eluksa@irb.hr), 7. Svi. 2012. u 08:53 sati



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