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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F12%3A33141460%21RIV13-MSM-15310___
rdf:type
n5:Vysledek skos:Concept
dcterms:description
Solid-phase synthesis of 3,4-dihydro-benzo[e][1,4]diazepin-5-ones with three diversity positions is described. Various primary amines were used as the starting material and immobilized on the polystyrene resin equipped with different acid-labile linkers. Polymer supported amines were converted to ?-aminoketones with the use of their sulfonylation with the 4-nitrobenzensulfonylchoride (4-Nos-Cl) and subsequent alkylation with alfa-bromoketones. After the cleavage of the 4-Nos group the corresponding -aminoketones were acylated with various o-nitrobenzoic acids. Reduction of the nitro group followed by spontaneous on-resin ring closure gave the target immobilized benzodiazepines. After acid-mediated cleavage the products were obtained in very good, crude purity and satisfactory yields which makes the developed method applicable for simple library synthesis of the corresponding derivatives in a combinatorial fashion. Solid-phase synthesis of 3,4-dihydro-benzo[e][1,4]diazepin-5-ones with three diversity positions is described. Various primary amines were used as the starting material and immobilized on the polystyrene resin equipped with different acid-labile linkers. Polymer supported amines were converted to ?-aminoketones with the use of their sulfonylation with the 4-nitrobenzensulfonylchoride (4-Nos-Cl) and subsequent alkylation with alfa-bromoketones. After the cleavage of the 4-Nos group the corresponding -aminoketones were acylated with various o-nitrobenzoic acids. Reduction of the nitro group followed by spontaneous on-resin ring closure gave the target immobilized benzodiazepines. After acid-mediated cleavage the products were obtained in very good, crude purity and satisfactory yields which makes the developed method applicable for simple library synthesis of the corresponding derivatives in a combinatorial fashion.
dcterms:title
Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives
skos:prefLabel
Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives
skos:notation
RIV/61989592:15310/12:33141460!RIV13-MSM-15310___
n5:predkladatel
n20:orjk%3A15310
n4:aktivita
n16:P
n4:aktivity
P(ED0030/01/01)
n4:cisloPeriodika
12
n4:dodaniDat
n14:2013
n4:domaciTvurceVysledku
n9:1759256 n9:5355346 n9:3181731 n9:4694554
n4:druhVysledku
n11:J
n4:duvernostUdaju
n18:S
n4:entitaPredkladatele
n13:predkladatel
n4:idSjednocenehoVysledku
169118
n4:idVysledku
RIV/61989592:15310/12:33141460
n4:jazykVysledku
n10:eng
n4:klicovaSlova
Benzodiazepines, Solid-phase synthesis, Aminoketones, Nitrobenzoic acids, Haloketones
n4:klicoveSlovo
n6:Nitrobenzoic%20acids n6:Benzodiazepines n6:Aminoketones n6:Solid-phase%20synthesis n6:Haloketones
n4:kodStatuVydavatele
US - Spojené státy americké
n4:kontrolniKodProRIV
[0CC36A59F590]
n4:nazevZdroje
ACS Combinatorial Science
n4:obor
n19:CC
n4:pocetDomacichTvurcuVysledku
4
n4:pocetTvurcuVysledku
4
n4:projekt
n15:ED0030%2F01%2F01
n4:rokUplatneniVysledku
n14:2012
n4:svazekPeriodika
14
n4:tvurceVysledku
Fülöpová, Veronika Gucký, Tomáš Grepl, Martin Soural, Miroslav
n4:wos
000312122500004
s:issn
2156-8952
s:numberOfPages
6
n17:doi
10.1021/co300124q
n12:organizacniJednotka
15310