7288-28-0Relevant academic research and scientific papers
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.
Molecular Assemblies of Metal Complexes via Base-Pairing of Nucleic Acids in the Crystalline State
Nakaya, Manabu,Ohtani, Ryo,Sugimoto, Kunihisa,Nakamura, Masaaki,Lindoy, Leonard F.,Hayami, Shinya
, p. 7232 - 7237 (2017)
The nature of the molecular assemblies formed in the crystalline state by cobalt(II) terpyridine (terpy) complexes incorporating appended adenine (A) or thymine (T) bases was found to be controlled by which bases are present. Single-crystals of the cobalt(II) complexes [Co(A-C6-terpy)2](BF4)2 (1) and [Co(T-C6-terpy)2](BF4)2 (2) have needle and block habits, respectively. Subsequent mixing of 1 and 2 in MeOH resulted in isolation of [Co(A-C6-terpy)1.5(T-C6-terpy)0.5](BF4)2 (3) as plate-like crystals. A 3D network structure is present in 1 that incorporates 1D chains, whereas 2 adopts a 2D stacked structure constructed from ladder-type assemblies. For 3, “dimer-rings” consisting of [Co(A-C6-terpy)2]2+ and [Co(A-C6-terpy)(T-C6-terpy)]2+ units are generated by means of base-pairing between A and T. Notably, 3 displays the first crystal structure of a heteroleptic cobalt(II) complex of [Co(A-C6-terpy)(T-C6-terpy)](BF4)2. These assembly differences involving the terpyridine cobalt(II) complex units in 1–3 affect the cooperativities influencing their spin crossover (SCO) behavior. The influence of the terminal nucleobases on the resulting assembly has been probed by investigating the co-crystallization of [Co(terpy)2](BF4)2 (4) with [Co(C6-terpy)2](BF4)2 (5) and 1 with 5.
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-
Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
Voss, Jürgen,Otzen, Dirk,Adiwidjaja, Gunadi
, p. 553 - 556 (2018)
1-(3′,5′-Anhydro-2′-deoxy-3′-thio-D-lyxo-furanosyl)thymine is prepared from the corresponding methyl pentofuranoside by using the silyl Hilbert-Johnson reaction. The α- and β-anomers are separated by column chromatography and their configuration is elucidated by NMR spectroscopy and, in case of the α-anomer, by an X-ray structure determination.
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.
Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: Synthesis of Methoxy TEMPO substituted pyrimidine nucleoside analogs
Church, Kevin M.,Holloway, Liesel M.,Matley, Ryan C.,Brower III, Robert J.
, p. 1723 - 1738 (2004)
Our work outlines the use of oxoammonium salts in a formal 1,2 addition process to olefins giving nucleoside analogs as products. Specifically, oxoammonium salts can be added to a solution of olefin and silylated heterocycle to give Methoxy TEMPO substituted nucleoside analogs after hydrolytic workup and chromatographic purification.
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.
Synthesis of 1-[cis-2-hydroxy-cis-3-(hydroxymethyl)-cyclobutyl]thymine, a novel method for the synthesis of cyclobutyl nucleosides and related compounds
Lin,Luo,Liu
, p. 245 - 254 (1994)
Syntheses of 1-[cis-2-hydroxy-cis-3-(hydroxymethyl)cyclobutyl]thymine (1) and related compounds by a novel method are reported. Coupling of 3- benzyloxymethyl-1-cyclobutene (2) with silylated thymine in the presence of NIS, followed by treatment with DBU, basic hydrolysis and catalytic hydrogenation produced the target compound (1) and its isomer (12).
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.
