35308-00-0Relevant articles and documents
Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition
Fascio, Mirta L.,D'Accorso, Norma Beatriz,Pellon, Rolando F.,Docampo, Maite L.
, p. 4209 - 4217 (2007)
Novel 10-{[3-(6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)- 4,5-dihydro-5-isoxazolyl]methyl}-9(10H)-acridinone derivatives (13-16) were synthesized by 1,3-dipolar cycloaddition using the carbohydrate derivative as dipole and different 10-allyl-9(10H)-acridinone derivatives (9-12) as dipolarophiles. The new cycloadducts as well as the dipolarophiles precursors were characterized spectroscopically. Copyright Taylor & Francis Group, LLC.
Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H-acridinone-1,2,3-triazoles
Mohammadi-Khanaposhtani, Maryam,Safavi, Maliheh,Sabourian, Reyhaneh,Mahdavi, Mohammad,Pordeli, Mahboobeh,Saeedi, Mina,Ardestani, Sussan Kabudanian,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
, p. 787 - 795 (2015/10/12)
A new series of 9(10H-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H-one 8c exhibited the most potency (hbox {IC}_{50},{=},11.0,{pm }, 4.8, upmu hbox {M})(IC50=11.0±4.8μM) against MCF-7 cells, being more potent than etoposide (hbox {IC}_{50},{=}, 12.4,{pm }, 4.7 upmu hbox {M})(IC50=12.4±4.7μM). Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.
Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and v
Marques, Emerson F.,Bueno, Mauro A.,Duarte, Patricia D.,Silva, Larissa R.S.P.,Martinelli, Ariani M.,Dos Santos, Caio Y.,Severino, Richele P.,Broemme, Dieter,Vieira, Paulo C.,Correa, Arlene G.
, p. 10 - 21 (2012/08/28)
Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L. The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors.
