17104-31-3Relevant articles and documents
Synthesis, Cytotoxicity Evaluation in Human Cell Lines and in Vitro DNA Interaction of a Hetero-Arylidene-9(10H)-Anthrone
Peixoto, Daniela,Figueiredo, Margarida,Malta, Gabriela,Roma-Rodrigues, Catarina,Baptista, Pedro V.,Fernandes, Alexandra R.,Barroso, Sónia,Carvalho, Ana Luísa,Afonso, Carlos A. M.,Ferreira, Luisa M.,Branco, Paula S.
, p. 545 - 549 (2018)
A new and never before reported hetero-arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally confirmed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed, indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity [Kb = 2.0 (±0.20) × 105 m–1], which is 10 × higher than that described for doxorubicin [Kb = 3.2 (±0.23) × 104 m–1]. Furthermore, compound 4 quenches the fluorescence emission of a GelRed–CT-DNA system with a quenching constant (KSV) of 3.3 (±0.3) × 103 m–1 calculated by the Stern–Volmer equation.
Endoperoxidation of 9,10-bis(1-hydroxyalkyl)-anthracenes and successive formation of 9,10-anthraquinone under Grignard reaction conditions
Kuroda, Shigeyasu,Oda, Mitsunori,Syumiya, Hiroki,Shaheen, Shah M. I.,Miyatake, Ryuta,Nishikawa, Teruhiko,Yoneda, Akiko,Tanaka, Tokiko,Mouri, Masaru,Kyogoku, Mayumi
, p. 153 - 159 (2007/10/03)
The reaction of anthracene-9,10-carboaldehyde with various Grignard reagents under ambient conditions gave 9,10-bis(1-hydroxyalkyl)anthracene-9,10-peroxides and 9,10-anthraquinone as the first example. The endoperoxidation of 9,10-bis(1-hydroxyalkyl)anthr
Products and Mechanism of the Oxidation of 9-Methylanthracene by Peroxydisulfate. Proton Loss and Nucleophile Addition Reactions of the 9-Methylanthracene Radical Cation
Deardurff, Larrie A.,Alnajjar, Mikhail S.,Camaioni, Donald M.
, p. 3686 - 3693 (2007/10/02)
The Cu(II)-S2O82- oxidation of 9-methylanthracene (1) was studied in refluxing CH3CN/acetic acid and aqueous CH3CN.Side-chain and nuclear oxidation products and the dimeric compound lepidopterene (7) were produced.The lepidopterene was determined to be formed by the reaction of intermediate anthracenylmethyl cation with 1.In CH3CN/H2O nuclear oxidation products, 10-hydroxy-10-methyl-9-anthrone (2) and 10-methylene-9-anthrone (3) and dimer 7 were produced, with the nuclear products predominating.In CH3CN/HOAc the dimer and side-chain substitution products, 1-OAc (5a) and 1-NHAc (5c), were predominant over the nuclear products, which consisted mainly of 3 and 10-acetoxy-9-methylanthracene (4a).A mechanism is proposed where the initially formed radical cation undergoes competing proton loss and reversible nucleophile addition reactions to form respectively the anthracenylmethyl radical and nucleophile adduct radicals.Oxidation of the radicals by Cu(II) or S2O82- yield the corresponding cations that react to form the products 4,5, and 7.Compounds 2 and 3 form by subsequent oxidation of the nuclear oxidation product, 10-methyl-9-anthrol.The results suggest that nucleophile addition is faster than proton loss and that it is more reversible in CH3CN/HOAc than in CH3CN/H2O
