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Statements

Subject Item
n2:RIV%2F00209805%3A_____%2F14%3A%230000516%21RIV15-MSM-00209805
rdf:type
skos:Concept n13:Vysledek
rdfs:seeAlso
http://pubs.acs.org/doi/abs/10.1021/om500200r
dcterms:description
Titanocene dichlorides of general formula [(η5-C5H5)(η5-C5H4R)TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α-D-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α-D-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C5H5)TiCl3] or a 0.5 mol amount of [TiCl4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5-C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu)2SnF 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 [(η5-C5H4R)2Fe] (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 [(η5-C5H4R)2Fe] (R = 5-deoxy-1,2-di-O-isopropylidene-α-D-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-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 [(η5-C5H4R1)(η5-C5H4R2)Fe] (R1 = Xylf and R2 = Xylf-OH (13)). The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard. Titanocene dichlorides of general formula [(η5-C5H5)(η5-C5H4R)TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α-D-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α-D-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C5H5)TiCl3] or a 0.5 mol amount of [TiCl4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5-C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu)2SnF 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 [(η5-C5H4R)2Fe] (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 [(η5-C5H4R)2Fe] (R = 5-deoxy-1,2-di-O-isopropylidene-α-D-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-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 [(η5-C5H4R1)(η5-C5H4R2)Fe] (R1 = Xylf and R2 = Xylf-OH (13)). The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.
dcterms:title
Titanocene dihalides and ferrocenes bearing a pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, characterization, and cytotoxic activity Titanocene dihalides and ferrocenes bearing a pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, characterization, and cytotoxic activity
skos:prefLabel
Titanocene dihalides and ferrocenes bearing a pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, characterization, and cytotoxic activity Titanocene dihalides and ferrocenes bearing a pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, characterization, and cytotoxic activity
skos:notation
RIV/00209805:_____/14:#0000516!RIV15-MSM-00209805
n3:aktivita
n15:I n15:P
n3:aktivity
I, P(ED2.1.00/03.0101), P(NT13794)
n3:cisloPeriodika
3
n3:dodaniDat
n9:2015
n3:domaciTvurceVysledku
n4:9637419 n4:3989151 n4:9919880 n4:1330586 n4:7947429
n3:druhVysledku
n18:J
n3:duvernostUdaju
n12:S
n3:entitaPredkladatele
n11:predkladatel
n3:idSjednocenehoVysledku
50628
n3:idVysledku
RIV/00209805:_____/14:#0000516
n3:jazykVysledku
n17:eng
n3:klicovaSlova
AGR3; GPC-3; intrahepatic cholangiocarcinoma; hepatocellular carcinoma; mucopolysaccharides; immunohistochemistry
n3:klicoveSlovo
n10:hepatocellular%20carcinoma n10:mucopolysaccharides n10:immunohistochemistry n10:GPC-3 n10:AGR3 n10:intrahepatic%20cholangiocarcinoma
n3:kodStatuVydavatele
US - Spojené státy americké
n3:kontrolniKodProRIV
[0EE658118D39]
n3:nazevZdroje
Experimental and molecular pathology
n3:obor
n19:FD
n3:pocetDomacichTvurcuVysledku
5
n3:pocetTvurcuVysledku
7
n3:projekt
n14:NT13794 n14:ED2.1.00%2F03.0101
n3:rokUplatneniVysledku
n9:2014
n3:svazekPeriodika
96
n3:tvurceVysledku
Brychtová, Veronika Hrstka, Roman Vojtěšek, Bořivoj Fabian, Pavel Novák, Jiří
n3:wos
000337212600016
s:issn
0014-4800
s:numberOfPages
7
n16:doi
10.1021/om500200r