56414-14-3

Usage

Preparation

Preparation by reaction of ethyl bromide with quinacetophenone in the presence of potassium hydroxide in boiling ethanol.

InChI:InChI=1/C10H12O3/c1-3-13-8-4-5-10(12)9(6-8)7(2)11/h4-6,12H,3H2,1-2H3

Upstream product

• 60-29-7 diethyl ether 
• 1205-91-0 benzene-1,4-diyl diacetate 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 141-52-6 sodium ethanolate 

Downstream Products

• 1632055-77-6 5-ethoxy-2,2-bis(4-nitrophenoxy)benzofuran-3(2H)-one 
• 1371663-79-4 C₁₇H₁₆O₄ 
• 1371663-71-6 C₁₇H₁₆O₄ 
• 1371663-63-6 4-(2-hydroxy-5-ethoxyphenyl)-6-phenyl-2-aminopyrimidine 
• 1247797-38-1 diethyl 3-(5-ethoxy-2-hydroxybenzoyl)-2,4-dimethylenepentanedioate 
• 536723-95-2 6-Ethoxy-4-hydroxy-coumarine 

Relevant academic research and scientific papers

A chromone derivative as a colorimetric and “ON-OFF-ON” fluorescent probe for highly sensitive and selective detection of Cu2+ and S2?

A chromone derivative (L) which could be utilized for reversibly detecting Cu2+ and S2? by means of fluorescence quenching and displacement in aqueous solution was designed and developed. Upon the addition of Cu2+, the strong blue-green fluorescence emission of L was quenched rapidly and then recovered in 1 min by successively adding S2?. Furthermore, with the alternate addition of Cu2+ and S2?, the reversible cycles could be repeated for at least four times, which meant that L could be identified as a renewable dual-functioning probe. What's more, due to its excellent sensing performances, this probe L could also be used to detect Cu2+ and S2? with test strips conveniently.

Effect of the Chromone Core Substitution of Dirchromone on the Resultant Biological Activities

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

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+.

A new off-on fluorescent sensor for the detection of Al(III) based on a chromone-derived Schiff-base

A new Al3+ sensor, 6-ethoxychromone-3-carbaldehyde-(3-hydroxy-2-naphthalene acyl) hydrazone (L), was designed and synthesized. The sensor L could exist steadily and detect Al3+ in the pH range from 5.0 to 8.0 in ethanol and water (3:1, v/v). This sensor showed good selectivity and high sensitivity towards Al3+ in the presence of most metal ions, and a remarkable enhancement in fluorescence emission intensity at 508 nm (λex = 420 nm) was observed with addition of 1equiv Al3+, which was attributed to the inhibition of photoinduced electron-transfer (PET) phenomenon and C[dbnd]N isomerization process. With the fluorescence titration experiments and the ESI-MS spectrum data, we reached the conclusion that the binding ratio between L and Al3+ was 2:1. Besides, the binding constant (Ka) between L and Al3+ was calculated to be 9.24 × 103 M?1 and the detection limit of L for Al3+ was as low as 1.82 × 10?7 M.

Coumarin, chromone, and 4(3H)-pyrimidinone novel bicyclic and tricyclic derivatives as antiplatelet agents: Synthesis, biological evaluation, and comparative molecular field analysis

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.

Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4- (4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ETA antagonism

A novel series of endothelin-A (ETA) selective receptor antagonists having a 2H-chromene skeleton are described. A lead compound, 2-(benzo[1,3] dioxol-5-yl)-2H-chromene-3-carboxylic acid (3), was found by modifications of our own angiotensin II antagonist. A structure-activity relationship (SAR) study of 3 reveals that the structural requirements essential for potent and selective ETA receptor binding affinity are the m,p-methylenedioxyphenyl, carboxyl, and isopropoxy groups at the 2-, 3-,and 6-positions, respectively, on the (R)-2H-chromene skeleton. The substituent at the 4-position is also important for improving the activity, and various hydrophobic functional groups of 6-9 ? such as liner, branched, and cyclic aliphatic groups, unsubstituted and substituted aryl groups, and even halogen atoms were acceptable. These results suggest that (R)-2-(benzo[1,3]dioxol-5-yl)-6-isopropoxy-2H-chromene-3-carboxylic acid, formula 108, is the crucial basic structure to be recognized by the ETA receptor. The most potent compound is (R)-48 (S-1255), which binds to the ETA receptor with an IC50 value of 0.19 nM and is 630-fold selective for the ETA receptor than for the ETB receptor. This compound has 55% oral bioavailability in rats. On the basis of the SAR, the roles of each substituent in the receptor binding are discussed.

Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes

Reactions of boron trifluoride methyl and ethyl etherate complexes with hydroquinone diesters yield monomethyl and monoethyl derivatives of acetylhydroquinones. The use of sterically hindered boron trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.