490-78-8Relevant academic research and scientific papers
(1,5)-Acetyl Shifts in Cycloadducts derived from 2-Acetyl-1,4-benzoquinones
Cooper, Simon C.,Sammes, Peter G.
, p. 633 - 634 (1980)
(1,5)-Acetyl shifts have been investigated in a number of cycloadducts prepared from 2-acetyl-1,4-benzoquinone and dienes, and it has been shown that the direction of migration depends on the nature of the diene substituents.
Synthesis and pharmacological evaluation of acylhydroquinone derivatives as potent antiplatelet agents
Méndez, Diego,Donoso-Bustamante, Viviana,Pablo Millas-Vargas, Juan,Pessoa-Mahana, Hernán,Araya-Maturana, Ramiro,Fuentes, Eduardo
, (2020/11/26)
Platelets are the smallest blood cells, and their activation (platelet cohesion or aggregation) at sites of vascular injury is essential for thrombus formation. Since the use of antiplatelet therapy is an unsolved problem, there are now focused and innovative efforts to develop novel antiplatelet compounds. In this context, we assessed the antiplatelet effect of an acylhydroquinone series, synthesized by Fries rearrangement under microwave irradiation, evaluating the effect of diverse acyl chain lengths, their chlorinated derivatives, and their dimethylated derivatives both in the aromatic ring and also the effect of the introduction of a bromine atom at the terminus of the acyl chain. Findings from a primary screening of cytotoxic activity on platelets by lactate dehydrogenase assay identified 19 non-toxic compounds from the 27 acylhydroquinones evaluated. A large number of them showed IC50 values less than 10 μM acting against specific pathways of platelet aggregation. The highest activity was obtained with compound 38, it exhibited sub-micromolar IC50 of 0.98 ± 0.40, 1.10 ± 0.26, 3.98 ± 0.46, 6.79 ± 3.02 and 42.01 ± 3.48 μM against convulxin-, collagen-, TRAP-6-, PMA- and arachidonic acid-induced platelet aggregation, respectively. It also inhibited P-selectin and granulophysin expression. We demonstrated that the antiplatelet mechanism of compound 38 was through a decrease in a central target in human platelet activation as in mitochondrial function, and this could modulate a lower response of platelets to activating agonists. The results of this study show that the chemical space around ortho-carbonyl hydroquinone moiety is a rich source of biologically active compounds, signaling that the acylhydroquinone scaffold has a promising role in antiplatelet drug research.
A chromone derivative as a colorimetric and “ON-OFF-ON” fluorescent probe for highly sensitive and selective detection of Cu2+ and S2?
Liu, Cong,Tian, Limei,Liu, Kui,Xue, Jia,Fan, Long,Li, Tianrong,Yang, Zheng-yin
, (2021/02/21)
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.
Iron-catalyzed arene C-H hydroxylation
Cheng, Lu,Wang, Huihui,Cai, Hengrui,Zhang, Jie,Gong, Xu,Han, Wei
, p. 77 - 81 (2021/10/05)
The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.
Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
, (2021/12/02)
American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
Bisketene Equivalents as Diels-Alder Dienes
Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.
supporting information, p. 13328 - 13333 (2020/09/03)
2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.
Assessing parameter suitability for the strength evaluation of intramolecular resonance assisted hydrogen bonding in O-carbonyl hydroquinones
Martínez-Cifuentes, Maximiliano,Monroy-Cárdenas, Matías,Millas-Vargas, Juan Pablo,Weiss-López, Boris E.,Araya-Maturana, Ramiro
, (2019/02/01)
Intramolecular hydrogen bond (IMHB) interactions have attracted considerable attention due to their central role in molecular structure, chemical reactivity, and interactions of biologically active molecules. Precise correlations of the strength of IMHB’s with experimental parameters are a key goal in order to model compounds for drug discovery. In this work, we carry out an experimental (NMR) and theoretical (DFT) study of the IMHB in a series of structurally similar o-carbonyl hydroquinones. Geometrical parameters, as well as Natural Bond Orbital (NBO) and Quantum Theory of Atoms in Molecules (QTAIM) parameters for IMHB were compared with experimental NMR data. Three DFT functionals were employed to calculated theoretical parameters: B3LYP, M06-2X, and ωB97XD. O . . . H distance is the most suitable geometrical parameter to distinguish among similar IMHBs. Second order stabilization energies ?Eij(2) from NBO analysis and hydrogen bond energy (EHB) obtained from QTAIM analysis also properly distinguishes the order in strength of the studied IMHB. ?Eij(2) from NBO give values for the IMHB below 30 kcal/mol, while EHB from QTAIM analysis give values above 30 kcal/mol. In all cases, the calculated parameters using ωB97XD give the best correlations with experimental1H-NMR chemical shifts for the IMHB, with R2 values around 0.89. Although the results show that these parameters correctly reflect the strength of the IMHB, when the weakest one is removed from the analysis, arguing experimental considerations, correlations improve significantly to values around 0.95 for R2
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+.
Half-wave potentials and in vitro cytotoxic evaluation of 3-acylated 2,5-bis(phenylamino)-1,4-benzoquinones on cancer cells
Benites, Julio,Valderrama, Jaime A.,Ramos, Maryan,Valenzuela, Maudy,Guerrero-Castilla, Angélica,Muccioli, Giulio G.,Calderon, Pedro Buc
, (2019/05/24)
A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.
Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition
Paghandeh, Hossein,Saeidian, Hamid,Ghaffarzadeh, Mohammad
, p. 809 - 814 (2018/09/26)
A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.
