78097-04-8Relevant academic research and scientific papers
Design, modeling & synthesis of 1,2,3-triazole-linked nucleoside-amino acid conjugates as potential antibacterial agents
Malkowski, Sarah N.,Dishuck, Carolyn F.,Lamanilao, Gene G.,Embry, Carter P.,Grubb, Christopher S.,Cafiero, Mauricio,Peterson, Larryn W.
, (2017/11/07)
Copper-catalyzed azide-alkyne cycloadditions (CuAAC or click chemistry) are convenient methods to easily couple various pharmacophores or bioactive molecules. A new series of 1,2,3- Triazole-linked nucleoside-amino acid conjugates have been designed and synthesized in 57-76% yields using CuAAC. The azido group was introduced on the 50-position of uridine or the acyclic analogue using the tosyl-azide exchange method and alkylated serine or proparylglycine was the alkyne. Modeling studies of the conjugates in the active site of LpxC indicate they have promise as antibacterial agents.
Synthesis of uracil nucleotide analogs with a modified, acyclic ribose moiety as P2Y2 receptor antagonists
Sauer, Roland,El-Tayeb, Ali,Kaulich, Marko,Mueller, Christa E.
experimental part, p. 5071 - 5079 (2009/11/30)
A series of new uracil nucleotide analogs (monophosphates, triphosphates, and phosphonates) was synthesized, in which the ribose moiety was replaced by acyclic chains, including branched or linear alkyl or dialkylether linkers. 1-ω-Bromoalkyluracil deriva
Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase
Nguyen, Corinne,Ruda, Gian Filippo,Schipani, Alessandro,Kasinathan, Ganasan,Leal, Isabel,Musso-Buendia, Alexander,Kaiser, Marcel,Brun, Reto,Ruiz-Pérez, Luis M.,Sahlberg, Britt-Louise,Johansson, Nils Gunnar,González-Pacanowska, Dolores,Gilbert, Ian H.
, p. 4183 - 4195 (2007/10/03)
We report the discovery of novel uracil-based acyclic compounds as inhibitors of deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase), an enzyme involved in nucleotide metabolism that has been identified as a promising target for the development of
A convenient one-pot synthesis of acyclonucleosides
Ubasawa,Takashima,Sekiya
, p. 142 - 143 (2007/10/02)
Bis(trimethylsilyl)pyrimidine bases were treated directly with 1,3-dioxolane (or 2-methyl-1,3-dioxolane), chlorotrimethylsilane and a metal iodide, such as KI or NaI, in acetonitrile at room temperature to afford acyclopyrimidine derivatives, including 2-thiopyrimidine derivatives, in good yields. Introduction of an acyclic chain into 2-thiopyrimidine bases, however, necessitated the use of 2 eq of the reagents.
Potentiation of the antitumor effect of 5-fluoro-2'-deoxyuridine esters in combination with acyclothymidine esters on L1210 in mice via oral administration
Kawaguchi,Saito,Saneyoshi
, p. 939 - 943 (2007/10/02)
Fifteen pyrimidine-related compounds were evaluated for their ability to inhibit enzymatic degradation of 5-fluoro-2'-deoxyuridine (FUdR). Acyclothymidine [5-methyl-1-(2'-hydroxyethoxymethyl)uracil] showed the highest inhibitory effect on the phosphorolytic degradation of FUdR in various tissue homogenates derived from mouse, rat, and beagle organs. Both the drug (FUdR) and the inhibitor (acyclothymidine) were esterified with appropriate aliphatic acids in order to synchronize their behavior after simultaneous oral administration. The antitumor activity of orally administered FUdR esters was potentiated by the simultaneous oral administration of the acyclothymidine esters, but not by acyclothymidine.
Synthesis of aliphatic nucleoside analogues with potential antiviral activity
Colla,Busson,De Clercq,Vanderhaeghe
, p. 569 - 576 (2007/10/02)
The synthesis of a series of double-modified adenosine and 8-aza-adenosine analogues, altered in the 6-position of the base and having the sugar moiety replaced by an acyclic hydroxylated side chain is described. Also, some aliphatic derivatives of 5-iodo- and E-5-(2-bromovinyl)uracil were prepared. Of all these compounds, only 6-hydroxylamino-9-(2,3-dihydroxypropyl)purine displayed some antiviral activity when tested in primary rabbit kidney cell cultures against vesicular stomatitis, vaccinia or herpes simplex virus.
Synthesis and Biological Effects of Acyclic Pyrimidine Nucleoside Analogues
Schroeder, Alan C.,Hughes, Robert G.,Bloch, Alexander
, p. 1078 - 1083 (2007/10/02)
A series of nucleoside analogues has been prepared, wherein the cyclic carbohydrate moiety is replaced by aliphatic side chains attached to cytosine, thymine, uracil, and 5-fluorouracil.The 1- derivatives of these heterocycles were synthesized by reacting the silylated bases with 2-(chloromethoxy)ethyl benzoate, followed by removal of the protecting groups with methanolic ammonia.The hydroxy group of a number of these derivatives was subsequently replaced by an azido, amino, or carbamoyloxy moiety.The 1-(2-oxo-3-butyl) and 1-(2-oxo-3-nonyl)derivatives of cytosine were also prepared, their synthesis being accomplished by condensation of the silylated heterocycle with the appropriate α-halo ketone.At 10-4 M concentrations, the newly prepared compounds were inactive against leukemia L-1210 cells in culture.However, a number of the agents inhibited the in vitro growth of Escherichia coli K-12, the most potent among these, 1--5-fluorouracil, being active at an IC50 of 1.2 μM.This compound was equally active in preventing the growth of a 5-fluorouracil resistant strain of E. coli.Some of the analogues were also found the selectively interfere with herpes simplex virus replication in vitro.None of the cytosine derivatives tested served as either substrates or inhibitors of human liver citosine nucleoside deaminase.
Pyrimidine Acyclic Nucleosides. 1-pyrimidines as Candidate Antivirals
Kelley, James L.,Kelsey, John E.,Hall, William R.,Krochmal, Mark P.,Schaeffer, Howard J.
, p. 753 - 756 (2007/10/02)
A number of pyrimidine acyclic nucleosides were synthesized and tested for activity against herpes simplex virus type 1.Synthesis of 1-cytosine (8) and 1-uracil (14) was accomplished in two or three steps
