About: Titanocene dihalides and ferrocenes bearing a pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, characterization, and cytotoxic activity     Goto   Sponge   NotDistinct   Permalink

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  • 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. (en)
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 (en)
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 (en)
skos:notation
  • RIV/00209805:_____/14:#0000516!RIV15-MSM-00209805
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(ED2.1.00/03.0101), P(NT13794)
http://linked.open...iv/cisloPeriodika
  • 3
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 50628
http://linked.open...ai/riv/idVysledku
  • RIV/00209805:_____/14:#0000516
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • AGR3; GPC-3; intrahepatic cholangiocarcinoma; hepatocellular carcinoma; mucopolysaccharides; immunohistochemistry (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [0EE658118D39]
http://linked.open...i/riv/nazevZdroje
  • Experimental and molecular pathology
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 96
http://linked.open...iv/tvurceVysledku
  • Brychtová, Veronika
  • Hrstka, Roman
  • Novák, Jiří
  • Vojtěšek, Bořivoj
  • Fabian, Pavel
http://linked.open...ain/vavai/riv/wos
  • 000337212600016
issn
  • 0014-4800
number of pages
http://bibframe.org/vocab/doi
  • 10.1021/om500200r
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