56414-14-3Relevant articles and documents
Effect of the Chromone Core Substitution of Dirchromone on the Resultant Biological Activities
St-Gelais, Alexis,Alsarraf, Jér?me,Legault, Jean,Plourde, Joanne,Pichette, André
, p. 2786 - 2794 (2021/12/02)
Dirchromone is a bioactive vinyl sulfoxide-bearing chromone first isolated from the shrub Dirca palustris. Altogether, 32 of its derivatives were prepared to assess the effect of substitution of its chromone core upon activities against cancer cell lines, Gram-positive bacteria, and fungi (such as Candida albicans). All compounds were synthesized following a synthetic strategy involving Pummerer and soft-enolization Baker-Venkataraman rearrangements. Substituent position changes induced little variability on the activities tested. There was no correlation between cytotoxic and antibacterial effects, suggesting different underlying mechanisms of action. In particular, hydroxy group and cyanide substituents diminished cytotoxicity, with the latter featuring enhanced antibacterial activity. Higher homologues of 6-alkoxydirchromones also exhibited progressively emerging antifungal activity. Other modifications had moderate effects on cytotoxicity with some derivatives leading to increased potency. This behavior highlights the robustness of the natural dirchromone pharmacophore toward decoration, thus paving the way for more elaborate future drug design.
A novel chromone derivative as dual probe for selective sensing of Al(III) by fluorescent and Cu(II) by colorimetric methods in aqueous solution
Tian, Limei,Xue, Jia,Li, Si-liang,Yang, Zheng-yin
, (2019/07/18)
Based on the chromone skeleton, a simple and novel probe that is 6-ethoxychromone-3-carbaldehyde-(furanyl) hydrazone (L) has been synthesized and completely characterized. It exhibited representative turn-on fluorescent properties and obviously colorimetric changes with high selectivity to Al3+ and Cu2+. For Al3+, L displayed a turn on green fluorescence in EtOH/H2O (3/2) aqueous media over other common cations. With Cu2+, L perceived Cu2+ through the naked-eye by the color changed-from colorless to yellow. Moreover, the coordination ratio between L-Al3+and L-Cu2+ was 1:1 which could be verified by the Job's plot, 1H NMR and high-resolution mass spectrum. Consequentially, L could be used as a solid probe for both Al3+ and Cu2+.
Coumarin, chromone, and 4(3H)-pyrimidinone novel bicyclic and tricyclic derivatives as antiplatelet agents: Synthesis, biological evaluation, and comparative molecular field analysis
Roma, Giorgio,Di Braccio, Mario,Carrieri, Antonio,Grossi, Giancarlo,Leoncini, Giuliana,Grazia Signorello, Maria,Carotti, Angelo
, p. 123 - 138 (2007/10/03)
As a further part of our chemical and biological studies in this field, we describe the multistep preparations of the properly substituted 2-(1-piperazinyl)chromone 1b, 4-(1-piperazinyl)coumarins 5c-h, their linear benzo-fused analogues 4a,b and 8a,b, bicyclic (15e-g) and tricyclic (15h,i) fused derivatives of 6-(1-piperazinyl)pyrimidin-4(3H)-one, and of the 4H-pyrido[1,2-a]pyrimidine derivatives 9b,c. The in vitro evaluation of their inhibitory properties towards human platelet aggregation induced in platelet-rich plasma by ADP, collagen, or the Ca 2+ionophore A23187 showed the high activity of compounds 5d-g and 15f,g,i, among which the coumarins 5g and 5d proved to be, in that order, the most effective in vitro antiplatelet agents until now synthesized by us. Thus, in order to consider also the 4-aminocoumarin structural class, we developed a new statistically significant 3-D QSAR model, more general than the one previously obtained, through a further CoMFA study based on the antiplatelet activity data and molecular steric and electrostatic potentials of both the previously studied and herein described compounds.
