- Synthesis and anticancer activity of some 5-fluoro-2′-deoxyuridine phosphoramidates
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Two series of novel 4-chlorophenyl N-alkyl phosphoramidates of 3′-O-(t-butoxycarbonyl)-5-fluoro-2′-deoxyuridine (3′-BOC-FdU) (9a-9j) and 5-fluoro-2′-deoxyuridine (FdU) (10a-10j) were synthesized by means of phosphorylation of 3′-BOC-FdU (4) with 4-chlorop
- Lewandowska, Marta,Ruszkowski, Piotr,Chojnacka, Kinga,Kleczewska, Natalia,Hoffmann, Marcin,Kacprzak, Karol,Celewicz, Lech
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- A convenient solid phase approach to obtain lipophilic 5′-phosphoramidate derivatives of DNA and RNA oligonucleotides
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This paper explores the potential of a modified phosphotriester approach to the synthesis of 5′-phosphoramidate derivatives of DNA and RNA oligonucleotides. The modification of 5′-deprotected support-bound oligonucleotides is done in two steps: i) conversion of the 5′-OH group of an oligonucleotide into an activated phosphodiester, and ii) treatment of the activated phosphodiester with an aminocompound. The approach is efficient and compatible with conventional solid phase oligonucleotide synthesis. It can be used for the conjugation of therapeutically relevant oligonucleotides with functional moieties or carrier constructions, which are to be removed after endocytosis.
- Dovydenko, Ilya S.,Kupryushkin, Maxim S.,Pyshnyi, Dmitrii V.,Apartsin, Evgeny K.
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Read Online
- Synthesis and anticancer activity of 3′-[4-fluoroaryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine analogs and their phosphoramidates
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A series of novel 4-chlorophenyl N-alkyl phosphoramidates of 3′-[4-fluoroaryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidines (20–49) was synthesized by means of phosphorylation of 3′-[4-aryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidines (7–11) with 4-chlorophenyl ph
- Kleczewska, Natalia,Ruszkowski, Piotr,Singh, Aleksandra,Trznadel, Roksana,Celewicz, Lech
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p. 605 - 641
(2019/04/17)
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- 2,3'-Anhydro-2'-deoxy-5-fluorouridine derivatives with cytotoxic activity, a manufacturing process and application
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The subject matter of the invention is novel 2,3'-anhydro-2'-deoxy-5-fluorouridine derivatives of general formula (1) where R is a trifluoromethyl, 2,2,2-trifluoroethyl, difluoromethyl, perfluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1,2-
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Page/Page column 13; 14
(2015/04/22)
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- Synthesis of novel 2′,3′-Didehydro-2′,3′- dideoxyinosine phosphoramidate prodrugs and evaluation of their anticancer activity
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An efficient synthesis of 4-chlorophenyl N-alkyl phosphoramidates of 2 ′,3 ′-didehydro-2 ′,3 ′-dideoxyinosine employing 4-chlorophenyl phosphoroditetrazolide as a phosphorylating agent is reported. Improved method for the synthesis of 2 ′,3 ′-didehydro-2
- Borek, Weronika,Lewandowska, Marta,Kleczewska, Natalia,Ruszkowski, Piotr,Kacprzak, Karol,Celewicz, Lech
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p. 507 - 518
(2014/08/05)
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- Synthesis of 3′-azido-2′,3′-dideoxy-5-fluorouridine phosphoramidates and evaluation of their anticancer activity
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A series of novel 4-chlorophenyl N-alkyl phosphoramidates of 3′-azido-2′,3′-dideoxy-5-fluorouridine (12-21) were synthesized by means of phosphorylation of 3′-azido-2′,3′- dideoxy-5-fluorouridine (4) with 4- chlorophenyl phosphoroditriazolide (10) followe
- Lewandowska, Marta,Ruszkowski, Piotr,Baraniak, Dagmara,Czarnecka, Anna,Kleczewska, Natalia,Celewicz, Lech
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p. 188 - 195
(2013/10/01)
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- Synthesis and polymerase chain reaction amplification of DNA strands containing an unnatural triazole linkage
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DNA strands containing an unnatural T-triazole-T linkage have been synthesized by click DNA ligation between oligonucleotides with 3′-AZT and 5′-propargylamido dT and amplified efficiently by polymerase chain reaction (PCR) using several different polymerases. DNA sequencing of PCR amplicons and clones in two different sequence contexts revealed the presence of a single thymidine at the ligation site. The remarkable ability of thermostable polymerases to reproducibly copy DNA templates containing such an unnatural backbone opens up intriguing possibilities in gene synthesis' genetic analysis' biology' and nanotechnology.
- El-Sagheer, Afaf H.,Brown, Tom
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experimental part
p. 3958 - 3964
(2009/09/04)
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- 5'-PHOSPHOURIDINE AS A SOURCE OF TERMINAL PHOSPHATE GROUPS IN OLIGONUCLEOTIDES
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A universal key component is proposed for the preparation of oligonucleotides with 3'- and 5'-terminal phosphate groups - 2',3'-dibenzoyluridin-5'-yl (4-chlorophenylphosphate) (pU(Bz)2), which is a potential source of the phosphate group.The condensation
- Oretskaya, T. S.,Krynetskaya, N. F.,Romanova, E. A.
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p. 610 - 613
(2007/10/02)
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- An Alternative to the Mixed Probe Method in DNA Hybridization: Synthetic "lure" Nucleotide for the Ambiguous Position of Codons
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Two deoxynucleoside analogues, 1-(2-deoxy-β-D-ribofuranosyl)-2-oxo-4-imidazoline-4-carboxamide (1) and 5-carbamoyl-2'-deoxyuridine (2), were synthesized and incorporated into decamer deoxynucleotides, which were hybridized to their complementary strands.T
- Fukuda, Tsunehiko,Hamana, Takumi,Kikuchi, Kaeko,Marumoto, Ryuji
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p. 1571 - 1579
(2007/10/02)
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