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排序方式: 共有91条查询结果,搜索用时 15 毫秒
1.
Dr. Sheng Cao Robin Christiansen Prof. Xiaohua Peng 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(27):9050-9058
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+Me3Br?, whereas electron‐donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH3 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. 相似文献
2.
Dr. Alberto Lena Dr. Alessandra Benassi Michele Stasi Christine Saint-Pierre Prof. Mauro Freccero Dr. Didier Gasparutto Dr. Sophie Bombard Prof. Filippo Doria Dr. Daniela Verga 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(35):e202200734
Combining the selectivity of G-quadruplex (G4) ligands with the spatial and temporal control of photochemistry is an emerging strategy to elucidate the biological relevance of these structures. In this work, we developed six novel V-shaped G4 ligands that can, upon irradiation, form stable covalent adducts with G4 structures via the reactive intermediate, quinone methide (QM). We thoroughly investigated the photochemical properties of the ligands and their ability to generate QMs. Subsequently, we analyzed their specificity for various topologies of G4 and discovered a preferential binding towards the human telomeric sequence. Finally, we tested the ligand ability to act as photochemical alkylating agents, identifying the covalent adducts with G4 structures. This work introduces a novel molecular tool in the chemical biology toolkit for G4s. 相似文献
3.
Melissa M. Cadelis Soeren Geese Benedict B. Uy Daniel R. Mulholland Shara J. van de Pas Alex Grey Bevan S. Weir Brent R. Copp Siouxsie Wiles 《Molecules (Basel, Switzerland)》2021,26(4)
Antimicrobial bioassay-guided fractionation of the endophytic fungi Neofusicoccum australe led to the isolation of a new unsymmetrical naphthoquinone dimer, neofusnaphthoquinone B (1), along with four known natural products (2–5). Structure elucidation was conducted by nuclear magnetic resonance (NMR) spectroscopic methods, and the antimicrobial activity of all the natural products was investigated, revealing 1 to be moderately active towards methicillin-resistant Staphylococcus aureus (MRSA) with a minimum inhibitory concentration (MIC) of 16 µg/mL. 相似文献
4.
Stereoselective catalytic synthesis of 3-trifluoromethyl indolines through the [4+1] cycloaddition of benzoxazinones and sulfur ylides in a transition-metal-free manner was developed. In the presence of a catalytic amount of sodium hydride, aza-ortho-quinone methide intermediates were formed from trifluoromethyl benzoxazinones through decarboxylation after the first nucleophilic attack of sulfur ylides, which progressed to a second nucleophilic attack of sulfur ylides, resulting in the [4+1] cycloaddition. The key for this catalytic transformation is the dual attack of sulfur ylides on substrates. This unique transition-metal-free protocol is applicable to the synthesis of non-fluorinated vinyl-, ethynyl- or methyl-substituted indolines. The synthesis of 3-trifluoromethyl indoles was also achieved described under stoichiometric conditions. 相似文献
5.
6.
A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
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Bryan S. Matsuura Mitchell H. Keylor Bo Li YuXuan Lin Shelby Allison Prof. Dr. Derek A. Pratt Prof. Dr. Corey R. J. Stephenson 《Angewandte Chemie (International ed. in English)》2015,54(12):3754-3757
An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical‐trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity. 相似文献
7.
V. M. Lyubchanskaya L. M. Alekseeva S. A. Savina V. G. Granik 《Chemistry of Heterocyclic Compounds》2003,39(1):61-64
The reaction of naphthoquinone with nitroenamines and the interaction of benzimidazolequinones with derivatives of -aminocrotonic ester have been studied. It was shown that in the first case only the synthesis of naphthofurans occurs but in the second imidazoindoles are formed. 相似文献
8.
N-Heterocyclic carbene-catalyzed 1,6-addition of aromatic aldehydes to para-quinone methides has been developed. This method could efficiently furnish α,α′-diarylated ketones with good to high yields, which contain various functional groups. 相似文献
9.
Jamie Hunter Scott Rice Robert Lowe Christopher M. Pask Stuart Warriner Visuvanathar Sridharan 《Tetrahedron letters》2017,58(46):4400-4402
2′-Hydroxyacetophenone was alkylated with a range of substituted benzyl and heteroaryl alcohols to afford the corresponding C-alkylated products in good yields under microwave irradiation. The C-alkylated products were reacted with bromoacetonitrile to afford 2-amino-3-benzyl 1,4-naphthoquinone derivatives in moderate yields. 相似文献
10.
IntroductionRecently ,wehavereportedthecoordinationchem istryof 1,2 naphthoquinone mono oxime (nqoH)towardsplatinumgroupmetalsincludingrutheniumandrhodi um .1 8ThereactionsofnqoHwithrutheniumcarbonyl[Ru3(CO) 12 ]leadtofiveisomersofmononuclearrutheni umcarbonylcomplexesof 1,2 naphthoquinone mono oxime .1 3Thepresenceoftheliablecarbonylligandsofferstheopportunitytointroduceavarietyofligandswithspe cificfunctionalgroupsintothemolecule .3Bythisstrategy ,metal containingpolymers ,supramolecular… 相似文献