C-alkylation of 1,4-dyhydroxynaphthalene with Tertiary Alcohols

Исследовано взаимодействие 1,4-дигидроксинафталина с третичными спиртами в трифторуксусной кислоте. Показано, что алкилирование происходит в положение 2 с последующей кето-енольной таутомерией и образованием 2-(1-трет.алкил)-2,3- дигидронафталин-1,4-дионов. С помощью 1H ЯМР-спектроскопии изучена кинетика кето- енольной перегруппировки 2-(1-адамантил)-2,3-дигидронафталин-1,4-диона в 2-(1-адамантил)- 1,4-дигидроксинафталин под действием морфолина. 2-(1-адамантил)-1,4-дигидроксинафталин быстро окисляется кислородом воздуха в 2-(1-адамантил)-1,4-нафтохинон.The interaction of 1,4-dyhydroxynaphthalene with tertiary alcohols in trifluoroacetic acid was investigated. It was shown, that alkylation occurred in position 2 with formation of 2-(tert.alkyl)- 2,3-dihydronaphthalene-1,4-diones. Kinetic of keto-enol tautomerization 2-(1-adamantyl)-2,3- dihydronaphthalene-1,4-dione into 2-(1-adamantyl)-1,4-dyhydroxynaphthalene by morpholine action was analyzed using 1H NMR spectroscopy. 2-(1-adamantyl)-1,4-dyhydroxynaphthalene was quickly oxidized into 2-(1-adamantyl)-1,4-naphthoquinone by atmospheric oxygen

Synthesis of Adamantane Derivatives of 1,6- and 1,7-dyhydroxynaphthalenes

Исследовано алкилирование адамантанолом-1 в среде трифторуксусной кислоты 1,6- и 1,7- дигидроксинафталинов. Разработан метод синтеза для соответствующих моно- и ди- адамантил производных.The interaction of 1,6- and 1,7-dyhydroxynaphthalenes with adamantanole-1 in trifluoroacetic acid was investigated. The method of synthetic procedure for corresponding mono- and di-adamantile derivatives was developed

C-alkylation of 1,4-dyhydroxynaphthalene with Tertiary Alcohols

Исследовано взаимодействие 1,4-дигидроксинафталина с третичными спиртами в трифторуксусной кислоте. Показано, что алкилирование происходит в положение 2 с последующей кето-енольной таутомерией и образованием 2-(1-трет.алкил)-2,3- дигидронафталин-1,4-дионов. С помощью 1H ЯМР-спектроскопии изучена кинетика кето- енольной перегруппировки 2-(1-адамантил)-2,3-дигидронафталин-1,4-диона в 2-(1-адамантил)- 1,4-дигидроксинафталин под действием морфолина. 2-(1-адамантил)-1,4-дигидроксинафталин быстро окисляется кислородом воздуха в 2-(1-адамантил)-1,4-нафтохинон.The interaction of 1,4-dyhydroxynaphthalene with tertiary alcohols in trifluoroacetic acid was investigated. It was shown, that alkylation occurred in position 2 with formation of 2-(tert.alkyl)- 2,3-dihydronaphthalene-1,4-diones. Kinetic of keto-enol tautomerization 2-(1-adamantyl)-2,3- dihydronaphthalene-1,4-dione into 2-(1-adamantyl)-1,4-dyhydroxynaphthalene by morpholine action was analyzed using 1H NMR spectroscopy. 2-(1-adamantyl)-1,4-dyhydroxynaphthalene was quickly oxidized into 2-(1-adamantyl)-1,4-naphthoquinone by atmospheric oxygen

Synthesis of Adamantane Derivatives of 1,6- and 1,7-dyhydroxynaphthalenes

Исследовано алкилирование адамантанолом-1 в среде трифторуксусной кислоты 1,6- и 1,7- дигидроксинафталинов. Разработан метод синтеза для соответствующих моно- и ди- адамантил производных.The interaction of 1,6- and 1,7-dyhydroxynaphthalenes with adamantanole-1 in trifluoroacetic acid was investigated. The method of synthetic procedure for corresponding mono- and di-adamantile derivatives was developed

Fucose-functionalized precision glycomacromolecules targeting human norovirus capsid protein

Norovirus infection is the major cause of non-bacterial gastroenteritis in humans and has been the subject of numerous studies investigating the virus’s biophysical properties and biochemical function with the aim of deriving novel and highly potent entry inhibitors to prevent infection. Recently, it has been shown that the protruding P domain dimer (P-dimer) of a GII.10 Norovirus strain exhibits two new binding sites for L-fucose in addition to the canonical binding sites. Thus these sites provide a novel target for the design of multivalent fucose ligands as entry inhibitors of norovirus infections. In this current study, a first generation of multivalent fucose-functionalized glycomacromolecules was synthesized and applied as model structures to investigate the potential targeting of fucose binding sites in human norovirus P-dimer. Following previously established solid phase polymer synthesis, eight precision glycomacromolecules varying in number and position of fucose ligands along an oligo(amidoamine) backbone were obtained and then used in a series of binding studies applying native MS, NMR and X-ray crystallography. We observed only one fucose per glycomacromolecule binding to one P-dimer resulting in similar binding affinities for all fucose-functionalized glycomacromolecules, which based on our current findings we attribute to the overall size of macromolecular ligands and possibly to steric hindrance