54503-61-6Relevant academic research and scientific papers
A novel one-step method for the synthesis of C-5-substituted O 6,5′-cyclopyrimidine nucleoside analogues in ammonia water
Qu, Gui-Rong,Ren, Bo,Niu, Hong-Ying,Mao, Zhi-Jie,Guo, Hai-Ming
, p. 2450 - 2453 (2008)
(Chemical Equation Presented) A novel one-step method for preparing C-5-substituted O6,5′-cyclopyrimidine nucleoside analogues is reported. This method employs molecular iodine to mediate the cyclization from the 5′-O-hydroxyl group of the sugar ring and C-6 at the position of the nitrogen base in ammonia water under mild conditions without any other aprotic organic solvent.
OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
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Paragraph 0639; 0640; 0641; 0757; 0758; 0759, (2018/01/19)
An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) {wherein X1 is an oxygen atom or the like, R1 is formula (IIA) (wherein R5A is halogen or the like, and R6A is a hydrogen atom or the like), formula (IVA) (wherein Y3A is a nitrogen atom or the like, and Y4A is CH or the like), or the like, R2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.
Lys314 is a nucleophile in non-classical reactions of orotidine-5′- monophosphate decarboxylase
Heinrich, Daniel,Diederichsen, Ulf,Rudolph, Markus Georg
supporting information; experimental part, p. 6619 - 6625 (2010/03/03)
Orotidine-5′-monophosphate decarboxylase (OMPD) catalyzes the decarboxylation of orotidine-5′-monophosphate (OMP) to uridine-5′-monophosphate (UMP) in an extremely proficient manner. The reaction does not require any cofactors and proceeds by an unknown mechanism. In addition to decarboxylation, OMPD is able to catalyze other reactions. We show that several C6-substituted UMP derivatives undergo hydrolysis or substitution reactions that depend on a lysine residue (Lys314) in the OMPD active site. 6-Cyano-UMP is converted to UMP, and UMP derivatives with good leaving groups inhibit OMPD by a suicide mechanism in which Lys314 covalently binds to the substrate. These non-classical reactivities of human OMPD were characterized by cocrystallization and freeze-trapping experiments with wildtype OMPD and two active-site mutants by using substrate and inhibitor nucleotides. The structures show that the C6-substituents are not coplanar with the pyrimidine ring. The extent of this substrate distortion is a function of the substituent geometry. Structurebased mechanisms for the reaction of 6-substituted UMP derivatives are extracted in accordance with results from mutagenesis, mass spectrometry, and OMPD enzyme activity. The Lys314based mechanisms explain the chemodiversity of OMPD, and offer a strategy to design mechanism-based inhibitors that could be used for antineoplastic purposes for example.
PYRIMIDINE DERIVATIVES AS ANTICANCER AGENTS
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Page/Page column 51, (2008/12/07)
The present invention includes methods of treating or preventing cancer by administering an effective amount of 6-substituted pyrimidine derivatives of the Formula I to a subject need thereof:
ODCASE INHIBITORS FOR THE TREATMENT OF MALARIA
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Page/Page column 51-52, (2008/06/13)
The present invention includes methods of treating or preventing malaria by administering an anti-malarial effective amount of 6-substituted uridine derivatives to a subject need thereof. The invention also includes new 6-substituted uridine derivatives for use as therapeutics, in particular to treat malaria.
Synthesis and anti-HCV activity of N9,5′-cyclo-3-(β- D-ribofuranosyl)-8-azapurin-2-one derivatives
Hassan, Abdalla E. A.,Wang, Peiyuan,McBrayer, Tamara,Tharnish, Philip,Stuyver, Lieven,Otto, Michael J.,Watanabe, Kyoichi A.,Schinazi, Raymond F.
, p. 1531 - 1542 (2007/10/03)
□ A number of 1- or 6-substituted N9,5′-cyclo-3- (β-D-ribofuranosyl)-8-azapurin-2-one derivatives were synthesized in multi-step reactions. Their anti-hepatitis C virus activities were evaluated and some structure-activity relationship is discussed. Copyright Taylor & Francis Group, LLC.
In-cell Indirect Electrochemical Halogenation of Pyrimidine Bases and their Nucleosides to 5-Haloderivatives
Palmisano, G.,Danieli, B.,Santagostino, M.,Vodopivec, B.,Fiori, G.
, p. 7779 - 7782 (2007/10/02)
Reaction of anodically generated "halonium" species (LiX or Bu4NX, LiClO4, MeCN, Pt/Pt; I2, LiClO4, MeCN) with pyrimidine bases and their nucleosides leads to 5-halo compounds in good yields.
Nucleosides. Part 5. Isolation and Characterization of the Stable Cyclic Adducts, (5R,6S)- and (5S,6S)-Bromo-O6,5'-cyclo-5,6-dihydrouridines in the Bromination of 2',3'-O-Isopropylideneuridine with N-Bromosuccinimide
Hirota, Kosaku,Tomishi, Tetsuo,Sako, Magoichi,Maki, Yoshifumi
, p. 2227 - 2232 (2007/10/02)
Bromination of 2'3'-O-isopropylidineuridine (1) with N-bromosuccinimide in chloroform containing acetic acid gave two diastreomeric cyclic adducts, (5R,6S)- and (5S,6S)-bromo-O6,5'-cyclo-5,6-dihydro-2',3'-O-isopropylideneuridines (4a) and (4b), whose structures were determined on the basis of their chemical reactivities and 1H n.m.r. spectral results.The cyclic adducts (4a) and (4b) formed an equilibrum mixture under acidic conditions , while under neutral and basic conditions both adducts were converted into 5-bromo-2',3'-O-isopropylidineuridine (2).
