7288-28-0Relevant articles and documents
Synthesis and antitumor activity of novel 2-(thymin-1′-ylmethoxy) ethyl alkyl sulfides and their oxidation products
Liu, Xue-Jun,Chen, Ru-Yu,Bai, Dong-Lu
, p. 2607 - 2616 (2005)
A series of novel 2-(thymin-1′-ylmethoxy)ethyl alkyl sulfides have been synthesized in three steps from thymine. They have been oxidized into sulfoxide and sulfone derivatives by means of NaIO4 and H 2O2 30%/diethyl azodicarboxylate (DEAD), respectively, in high yields. All products were characterized by 1H NMR and IR spectra and elemental analyses. The preliminary bioassay indicates that the compound 6g exhibited potential antitumor activity. Copyright Taylor & Francis Inc.
Efficient formation of H-addition radical and secondary alkyl radical in pentylthymines γ-irradiated at 77 K
Ohta, Nobuaki,Tanaka, Noriyuki,Ito, Sotaro
, p. 2597 - 2602 (1999)
EPR detection of three pentylthymines γ-irradiated at 77 K showed the production of a 5,6-dihydro-5-thymyl radical (5-thymyl radical) as an H-addition radical and a secondary alkyl radical formed by C-H bond fission at the second carbon from the end of the pentyl group. The introduction of the pentyl group into thymine increased total radical yields at 77 K up to about twice that of thymine and considerably enhanced 5-thymyl radical yields. Several discussions on the radical formation suggest that the efficient production of 5-thymyl radical is related to the concomitant formation of the secondary radical.
Synthesis of 1′-[14C]-stavudine (d4T)
Discordia, Robert P.
, p. 613 - 623 (1996)
1-(1′-[ 14C]-2′,3′-Dideoxy-β-D-glyceropent-2′- enofuranosyl)thymine (1′-[14C]-d4T), was synthesized from 1-[14C]-ribose, 1, in 7 steps in an overall yield of 29.3%. 1-[14C]-Ribose was converted in one step to 1-
Synthesis of the four 1-(1-deoxy-d-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain
Vejcik, Scott M.,Horton, Derek
, p. 806 - 818 (2007)
Acetylated d-pentose diethyl dithioacetals were coupled by way of 1-bromo-1-ethylthio derivatives with 2,4-bis(trimethylsilyl)thymine to afford diastereomeric pairs of acyclic-sugar nucleoside analogues bearing a thymin-1-yl and an ethylthio group at C-1. Free-radical desulfurization by the action of tributylstannane removed the ethylthio group to afford the corresponding acetylated 1-(1-deoxy-d-pentitol-1-yl)thymines and subsequently the free title compounds in the arabino, lyxo, ribo, and xylo series. Conformations of the intermediates and products were studied in detail and the final products were evaluated for their potential as agents active against plant viruses and rice blast fungus.
Synthesis of bicyclo-DNA nucleosides with additional functionalization in the carbocyclic ring
Luisier, Samuel,Leumann, Christian J.
, p. 270 - 272 (2008)
Two novel bicyclo nucleoside isomers carrying the base thymine in the furanose ring and an ester substituent in the carbocyclic ring were synthesized from a common bicyclic sugar precursor via a cyclopropanation/ fragmentation pathway in nine steps. The relative configuration of the ester substituent in both isomers as well as the anomeric configuration in one nucleoside was determined by 1H-NMR difference NOE spectroscopy. Schweizerische Chemische Gesellschaft.
Sodium cation complexation in a macrocycle containing thymines as sidearm donor groups
De Wall, Stephen L.,Barbour, Leonard J.,Schall, Otto F.,Gokel, George W.
, p. 227 - 231 (2000)
Previous studies of macrocycles having alkyl sidearms terminated in adenine or thymine have been focused on intermolecular association. Electrospray mass spectrometric analyses suggested that sodium complexation could be a major alternative process in the presence of the appropriate cation. Sodium cation complexation by N,N′-bis(3-(1-thyminyl)propyl)-4,13-diaza-18-crown-6 has been confirmed by X-ray crystallographic analysis. A sodium cation is bound in the center of the macroring. The four ether oxygens and two thyminyl carbonyl donors have the shortest contacts with the two, macroring nitrogen atoms being somewhat more remote. Neither the iodide counterion nor an acetone of solvation appears to interact with the sodium cation. Crystal Data: Triclinic, P1, a = 11.9371(12), b = 12.1588(13), c = 13.7885(14) A, α = 78.083(2)°, β = 83.213(2)°, γ = 78.997(2)°, and Dcalc = 1.392 g cm-3, Ζ= 2.
Chemical synthesis and properties of long-chain alkoxymethyl-nucleobase derivatives
Kovalenko,Madre,Lindau,Bohley,Panchenko,Meister,Zhuk,Hoffmann
, p. 1813 - 1821 (1998)
New nucleobase derivatives were synthesized, containing both octyloxymethyl (LCAS) and octadecyloxymethyl (LCA18) substituents at N1 position of pyrimidine and N9 of purine. These substances were studied with respect to the formation of supramolecular structures, i.a. molecular associates as the result of noncovalent interactions. Special attention has been paid to complex formation. The properties of these molecules were investigated by DSC and polarizing microscopy.
Lignin Nanoparticles Deliver Novel Thymine Biomimetic Photo-Adducts with Antimelanoma Activity
Gabellone, Sofia,Piccinino, Davide,Filippi, Silvia,Castrignanò, Tiziana,Zippilli, Claudio,Del Buono, Davide,Saladino, Raffaele
, (2022/01/20)
We report here the synthesis of novel thymine biomimetic photo-adducts bearing an alkane spacer between nucleobases and characterized by antimelanoma activity against two mutated cancer cell lines overexpressing human Topoisomerase 1 (TOP1), namely SKMEL28 and RPMI7951. Among them, Dewar Valence photo-adducts showed a selectivity index higher than the corresponding pyrimidine-(6-4)-pyrimidone and cyclobutane counterpart and were characterized by the highest affinity towards TOP1/DNA complex as evaluated by molecular docking analysis. The antimelanoma activity of novel photo-adducts was retained after loading into UV photo-protective lignin nanoparticles as stabilizing agent and efficient drug delivery system. Overall, these results support a combined antimelanoma and UV sunscreen strategy involving the use of photo-protective lignin nanoparticles for the controlled release of thymine dimers on the skin followed by their sacrificial transformation into photo-adducts and successive inhibition of melanoma and alert of cellular UV machinery repair pathways.
S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS
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Paragraph 0056; 0332, (2021/06/22)
Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.
Practical and reliable synthesis of 2′,3′,5′,5″-tetradeuterated uridine derivatives
Miyamoto, Noriko,Ohno, Hiroki,Kitamura, Yoshiaki,Park, Kwihwan,Sawama, Yoshinari,Sajiki, Hironao,Kitade, Yukio
, p. 236 - 244 (2019/11/13)
Deuterated drugs are valuable in the fields of drug discovery and medicinal chemistry. 2′,3′,5′,5″-tetradeuterated uridine derivatives were synthesised from 2,3,5,5′-selectively tetradeuterated ribose using Sajiki’s H–D exchanged Ru/C–H2–D2O–NaOH system and silyl–Hilbert–Johnson methods. The total deuterium content of the tetradeuterated uridines was over 92% using either basic or acidic reaction conditions. These derivatives would be expected as building blocks for the synthesis of deuterium-substituted nucleic acid probes for tracking the pharmacokinetics of nucleic acid drugs.
