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

Škalamera, Đani; Mlinarić-Majerski, Kata; Martin-Kleiner, Irena; Kralj, Marijeta; Wan, Peter; Basarić, Nikola (2014) Near-visible light generation of a quinone methide from 3-hydroxymethyl-2-anthrol. Journal of organic chemistry, 79 (10). pp. 4390-4397. ISSN 0022-3263

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: quinone methide; laser flash photolysis (LFP); 3-hydroxymethyl-2-anthrol; anthrol
Subjects: NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Fotokemija policikličkih molekula: od istraživanja mehanizma reakcije do novih lijekova i medicinskih primjena-Nikola BasarićUIP-02.05/25HRZZ
Cage Compounds: Building Blocks for Molecular Architecture (Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima)-Kata Majerski098-0982933-2911MZOS
Depositing User: Enidija Lukša
Date Deposited: 26 Jan 2016 14:01
Last Modified: 05 May 2017 09:02
URI: http://fulir.irb.hr/id/eprint/2425
DOI: 10.1021/jo500290y

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