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Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol (CROSBI ID 205472)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Škalamera, Đani ; Mlinarić-Majerski, Kata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Wan, Peter ; Basarić, Nikola Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol // Journal of organic chemistry, 79 (2014), 10; 4390-4397. doi: 10.1021/jo500290y

Podaci o odgovornosti

Škalamera, Đani ; Mlinarić-Majerski, Kata ; Martin-Kleiner, Irena ; Kralj, Marijeta ; Wan, Peter ; Basarić, Nikola

engleski

Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol

Excitation of 2-hydroxy-3-(diphenylhydroxymethyl)anthracene (7) to S1 initiates photodehydration giving the corresponding quinone methide (QM) that was detected by laser flash photolysis (LFP) in 2, 2, 2-trifluoroethanol TFE (λ = 580 nm, τ = 690 ± 10 ns). The QM decays by protonation, giving cation (λ = 520 nm, τ = 84 ± 3 μs) which subsequently reacts with nucleophiles. The rate constants in the reactions with nucleophiles were determined by LFP, whereas the adducts were isolated via preparative photolyses. The photogeneration of QMs in the anthrol series is important for potential use in biological systems since the chromophore absorbs at wavelengths > 400 nm. Antiproliferative investigations conducted with 2-anthrol derivative 7 on three human cancer cell lines showed higher activity for irradiated cells.

quinone methide ; laser flash photolysis (LFP) ; 3-hydroxymethyl-2-anthrol ; anthrol

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Podaci o izdanju

79 (10)

2014.

4390-4397

objavljeno

0022-3263

10.1021/jo500290y

Povezanost rada

Kemija, Temeljne medicinske znanosti

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