41951-76-2Relevant academic research and scientific papers
Regioselective synthesis of gentisyl alcohol-type marine natural products
Wang, Hong-Shuang,Li, Hui-Jing,Wang, Long-Fei,Shen, Zhi-Lun,Wu, Yan-Chao
supporting information, p. 1891 - 1896 (2018/05/29)
Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.
Rhodium-Catalyzed Annulations of 1,3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein
Li, Hong-Shuang,Xiong, Yang,Zhang, Guozhu
supporting information, p. 4246 - 4251 (2018/10/02)
A rhodium-catalyzed 2-ethylacrolein-promoted protocol enables the annulation reactions of 1,3-dienes with either salicylaldehydes or 2-hydroxybenzyl alcohols leading to 2-alkylchroman-4-ones with high regioselectivity. This research highlights the use of 2-ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4-hydroacylation pathway to access unsaturated linear ketones with subsequent oxo-Michael addition. (Figure presented.).
Preparation method of sateripol compounds
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Paragraph 0010; 0011, (2017/03/18)
The invention relates to a preparation method of sateripol compounds, and belongs to the field of chemical synthesis. 4-alkoxy saligenol compounds are prepared by carrying out a reaction of 4-alkoxy phenol compounds and aldehyde ketone compounds, the gent
Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system
Li, Hui-Jing,Wu, Ying-Ying,Wu, Qin-Xi,Wang, Rui,Dai, Chun-Yang,Shen, Zhi-Lun,Xie, Cheng-Long,Wu, Yan-Chao
, p. 3100 - 3107 (2014/05/06)
Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system generates salicyl alcohols in 65-97% yields. A remarkable rate-enhancement by water was observed, and NaBO2 appeared to serve the dual role of a suitable base and an efficient chelating reagent. This protocol possesses many advantages such as short reaction times, expanded substrate scope, and high mono- and regio-selectivities. The experimental results were explained by the calculations based on local ionisation energy minima, leading to a possible reaction mechanism.
Substituent effect on the photochemistry of 4,4-dialkoxylated- and 4-hydroxylated cyclohexenones
Chen, Yu-Jen,Wang, Hui-Ling,Villarante, Nelson R.,Chuang, Gary Jing,Liao, Chun-Chen
, p. 9591 - 9599 (2013/10/22)
Photochemistry of the title compounds in various solvents was studied using a broad band of light centered at 350 nm. C-4 spiroketal cyclohexenone 4 (1.0 M) afforded dimers and 12b with the predominance of the former in polar solvent and the latter in non
MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations
Ferino, Giulio,Cadoni, Enzo,Matos, Maria Joao,Quezada, Elias,Uriarte, Eugenio,Santana, Lourdes,Vilar, Santiago,Tatonetti, Nicholas P.,Yanez, Matilde,Vina, Dolores,Picciau, Carmen,Serra, Silvia,Delogu, Giovanna
, p. 956 - 966 (2013/07/27)
Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.
Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors
Cao, Sheng,Christiansen, Robin,Peng, Xiaohua
, p. 9050 - 9058 (2013/07/26)
A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br -) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiological conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me 3Br-, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH 3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiological conditions. Finally, a quantitative relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation. Tunable quinone methide formation: Aromatic substituents and the benzylic leaving group strongly affect the H 2O2-induced formation of quinone methides (QMs) from arylboronic esters (see scheme). The reactivity of arylboronic esters can be predictably adjusted by varying substituents. Copyright
Dual reactivity of hydroxy- and methoxy- substituted o-Quinone methides in aqueous solutions: Hydration versus tautomerization.
Arumugam, Selvanathan,Popik, Vladimir V.
scheme or table, p. 7338 - 7346 (2011/01/12)
4-Hydroxy-6-methylene-2,4-cyclohexadien-1-one (1) and 4-methoxy-6- methylene-2,4-cyclohexadien-1-one (2) were generated by efficient (Φ = 0.3) photodehydration of 2-(hydroxymethyl)benzene-1,4-diol (3a) and 2-(hydroxymethyl)-4-methoxyphenol (4a), respectively. o-Quinone methides 1 and 2 can be quantitatively trapped as Diels-Alder adducts with ethyl vinyl ether or intercepted by good nucleophiles, such as azide ion (kN3(1) = 3.15 × 104 M-1 s-1 and kN3(2) = 3.30 × 104 M-1 s-1). In aqueous solution, o-quinone methide 2 rapidly adds water to regenerate starting material (τH2O(2) = 7.8 ms at 25 °C). This reaction is catalyzed by specific acid (kH+(2) = 8.37 × 10 3 s-1 M-1) and specific base (k OH-(2) = 1.08 × 104 s-1 M -1) but shows no significant general acid/base catalysis. In sharp contrast, o-quinone methide 1 decays (τH2O(1) = 3.3 ms at 25 °C) via two competing pathways: nucleophilic hydration to form starting material 3a and tautomerization to produce methyl-p-benzoquinone. The disappearance of 1 shows not only specific acid (kH+(1) = 3.30 × 104 s-1 M-1) and specific base catalysis (kOH-(1) = 3.51 × 104 s -1 M-1) but pronounced catalysis by general acids and bases as well. The o-quinone methides 1 and 2 were also generated by the photolysis of 2-(ethoxymethyl)benzene-1,4-diol (3b) and 2-(ethoxymethyl)-4- methoxyphenol (4b), as well as from (2,5-dihydroxy-1-phenyl)methyl- (3c) and (2-hydroxy-5-methoxy-1-phenyl)methyltrimethylammonium iodides (4c). Short-lived (τ25°C ≈ 20 μs) precursors of o-quinone methides 1 and 2 were detected in the laser flash photolysis of 3a,b and 4a,b. On the basis of their reactivity, benzoxete structures have been assigned to these intermediates.
Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties
Bertini, Simone,Calderone, Vincenzo,Carboni, Isabella,Maffei, Roberta,Martelli, Alma,Martinelli, Adriano,Minutolo, Filippo,Rajabi, Mehdi,Testai, Lara,Tuccinardi, Tiziano,Ghidoni, Riccardo,MacChia, Marco
experimental part, p. 6715 - 6724 (2010/10/19)
New resveratrol (RES) analogs were developed by replacing the aromatic 'core' of our initial naphthalene-based RES analogs with pseudo-heterocyclic (salicylaldoxime) or heterocyclic (benzofuran, quinoline, and benzothiazole) scaffolds. The resulting analo
Biomimetic formation of 2-tropolones by dioxygenase-catalysed ring expansion of substituted 2,4-cyclohexadienones
Xin, Meite,Bugg, Timothy D. H.
experimental part, p. 272 - 276 (2010/10/21)
Substituted 2-tropolone natural products are found in plants and fungi. Their biosynthesis is thought to occur by ring expansion from a cyclohexadienone precursor, but this reaction has not previously been demonstrated experimentally. Treatment of 6-hydroxy-6-hydroxymethylcyclohexa-2,4-dienone with the non-haem iron(II)-dependent extradiol catechol dioxygenase MhpB from Escherichia coli results in the formation of the 2-tropolone ring-expansion product through a pinacol-type rearrangement. Three further substituted cyclohexa-2,4-dienone analogues were prepared, and treatment of each analogue was found to give the substituted 2-tropolone ring-expansion product. This ring expansion could also be effected nonenzymatically by treatment with 1,4,7-triazacyclononane and FeCl2. This is a novel transformation for non-haem iron-dependent enzymes, and this is the first experimental demonstration of the proposed ring-expansion reaction in tropolone biosynthesis.
