77887-18-4Relevant academic research and scientific papers
Metallo-nucleosides: Synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2′-deoxyuridines
Sergeant, Craig D.,Ott, Ingo,Sniady, Adam,Meneni, Srinivasarao,Gust, Ronald,Rheingold, Arnold L.,Dembinski, Roman
, p. 73 - 80 (2008/09/20)
Reactions of 5-alkynyl-2′-deoxyuridines with dicobalt octacarbonyl Co2(CO)8 in THF at room temperature gave hexacarbonyl dicobalt nucleoside complexes (77-93%). The metallo-nucleosides were characterized, including an X-ray structure
5-Alkynyl-2′-deoxyuridines: Chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells
Meneni, Srinivasarao,Ott, Ingo,Sergeant, Craig D.,Sniady, Adam,Gust, Ronald,Dembinski, Roman
, p. 3082 - 3088 (2008/02/01)
Starting with 5-iodo-2′-deoxyuridine, a series of 5-alkynyl-2′-deoxyuridines (with n-propyl, cyclopropyl, 1-hydroxycyclohexyl, p-tolyl, p-tert-butylphenyl, p-pentylphenyl, and trimethylsilyl alkyne substituents) have been synthesized via the palladium-cat
Design and studies of novel 5-substituted alkynylpyrimidine nucleosides as potent inhibitors of mycobacteria
Rai, Dinesh,Johar, Monika,Manning, Tracey,Agrawal,Kunimoto, Dennis Y.,Kumar, Rakesh
, p. 7012 - 7017 (2007/10/03)
We herein report a new category of 5-substituted pyrimidine nucleosides as potent inhibitors of mycobacteria. A series of 5-alkynyl derivatives of 2′-deoxyuridine (1-8), 2′-deoxycytidine (9-14), uridine (15-17), and 2′-O-methyluridine (18, 19) were synthe
Oligonucleotide analogs capable of passive cell membrane permeation
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, (2008/06/13)
Oligonucleotides that are capable of passive diffusion across cell membranes are disclosed. These oligonucleotides contain at least two nucleotide residues and show a log distribution coefficient in octanol:water of about 0.0-2.5 and a solubility in water
Nucleic Acid Related Compounds. 39. Efficient Conversion of 5-Iodo to 5-Alkynyl and Derived 5-Substituted Uracil Bases and Nuleosides
Robins, Morris J.,Barr, Philip J.
, p. 1854 - 1862 (2007/10/02)
Coupling of terminal alkynes with 5-iodo-1-methyl-uracil and 5-iodouracil nucleosides (protected as their p-toluyl esters) proceeded in high yields in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I)iodide in warm triethylamine.Several of the subsequently deprotected 5-alkynyl-2'-deoxyuridines, including the parent 5-ethynyl-2'-deoxyuridine, had antiviral activity, and their 5'-monophosphates inhibited thymidylate synthetase.Hydrogenation of the 5-alkynyl side chain can be controlled to give (Z)-5-alkenyl- or the saturated 5-alkyl-2'-deoxyuridines.This provides a stereocontrolled route to the known 5-ethyl-and 5-n-hexyl-2'-deoxyuridines as well as (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU).Hydration of the triple bond gave the corresponding uracil-5-alkanone products in favorable cases.
NUCLEIC ACID RELATED COMPOUNDS. 31. SMOOTH AND EFFICIENT PALLADIUM-COPPER CATALYZED COUPLING OF TERMINAL ALKYNES WITH 5-IODOURACIL NUCLEOSIDES
Robins, Morris J.,Barr, Philip J.
, p. 421 - 424 (2007/10/02)
Coupling of terminal alkynes with protected 5-iodouracil nucleosides in the presence of dichlorobis(triphenylphosphine)palladium and copper(I) iodide in triethylamine gives the corresponding 5-(alkyn-1-yl)uracil nucleosides in 72-92percent yields.
