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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F14%3A10277912%21RIV15-MSM-11310___
rdf:type
skos:Concept n20:Vysledek
rdfs:seeAlso
http://dx.doi.org/10.1021/om500200r
dcterms:description
Titanocene dichlorides of general formula [(eta(5)-C5H5)(eta(5)-C5H4R)TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-ribofuranos-5-yl (Ribf) (8b)) and [(eta(5)-C5H4R)(2)TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(eta(5)-C5H5)TiCl3] or a 0.5 mol amount of [TiCl4(THF)(2)]. Titanocene difluorides of the general formula [(eta(5)-C5H4R1)(eta(5)-C5H4R2)TiF2] (R-1 = H and R-2 = Ribf (10); R-1 = R-2 = Xylf (11a); R-1 = R-2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-kappa C,N}(n-Bu)(2)SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)(2)] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(eta(5)-C5H4R)(2)Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(eta(5)-C3H4R)(2)Fe] (R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(eta(5)-C5H4R1)(eta(5)-C5H4R2)Fe] (R-1 = Xylf and R-2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. Titanocene dichlorides of general formula [(eta(5)-C5H5)(eta(5)-C5H4R)TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-alpha-D-ribofuranos-5-yl (Ribf) (8b)) and [(eta(5)-C5H4R)(2)TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(eta(5)-C5H5)TiCl3] or a 0.5 mol amount of [TiCl4(THF)(2)]. Titanocene difluorides of the general formula [(eta(5)-C5H4R1)(eta(5)-C5H4R2)TiF2] (R-1 = H and R-2 = Ribf (10); R-1 = R-2 = Xylf (11a); R-1 = R-2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-kappa C,N}(n-Bu)(2)SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)(2)] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(eta(5)-C5H4R)(2)Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(eta(5)-C3H4R)(2)Fe] (R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-alpha-D-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(eta(5)-C5H4R1)(eta(5)-C5H4R2)Fe] (R-1 = Xylf and R-2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis.
dcterms:title
Titanocene Dihalides and Ferrocenes Bearing a Pendant alpha-D-Xylofuranos-5-yl or alpha-D-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity Titanocene Dihalides and Ferrocenes Bearing a Pendant alpha-D-Xylofuranos-5-yl or alpha-D-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity
skos:prefLabel
Titanocene Dihalides and Ferrocenes Bearing a Pendant alpha-D-Xylofuranos-5-yl or alpha-D-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity Titanocene Dihalides and Ferrocenes Bearing a Pendant alpha-D-Xylofuranos-5-yl or alpha-D-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity
skos:notation
RIV/00216208:11310/14:10277912!RIV15-MSM-11310___
n4:aktivita
n6:Z n6:I
n4:aktivity
I, Z(MSM0021620857)
n4:cisloPeriodika
8
n4:dodaniDat
n7:2015
n4:domaciTvurceVysledku
n14:3157962
n4:druhVysledku
n15:J
n4:duvernostUdaju
n19:S
n4:entitaPredkladatele
n8:predkladatel
n4:idSjednocenehoVysledku
50627
n4:idVysledku
RIV/00216208:11310/14:10277912
n4:jazykVysledku
n10:eng
n4:klicovaSlova
modular synthesis; functional titanocenes; organometallic compounds; carbohydrate chloroquine; dichloride derivatives; anticancer drugs; human serum transferrin; cyclic alkylammonium groups; potential antimalarial agents; benzyl-substituted titanocenes
n4:klicoveSlovo
n5:cyclic%20alkylammonium%20groups n5:organometallic%20compounds n5:functional%20titanocenes n5:dichloride%20derivatives n5:modular%20synthesis n5:benzyl-substituted%20titanocenes n5:potential%20antimalarial%20agents n5:carbohydrate%20chloroquine n5:human%20serum%20transferrin n5:anticancer%20drugs
n4:kodStatuVydavatele
US - Spojené státy americké
n4:kontrolniKodProRIV
[E25FC61F4237]
n4:nazevZdroje
Organometallics
n4:obor
n12:CF
n4:pocetDomacichTvurcuVysledku
1
n4:pocetTvurcuVysledku
8
n4:rokUplatneniVysledku
n7:2014
n4:svazekPeriodika
33
n4:tvurceVysledku
Císařová, Ivana Hrstka, Roman Červenková Šťastná, Lucie Lamač, Martin Pinkas, Jiří Karban, Jindřich Koubkova, Lucie Hodík, Tomáš
n4:wos
000335201600022
n4:zamer
n9:MSM0021620857
s:issn
0276-7333
s:numberOfPages
12
n16:doi
10.1021/om500200r
n18:organizacniJednotka
11310