3310-47-2Relevant academic research and scientific papers
Novel cytidine-based orotidine-5′-monophosphate decarboxylase inhibitors with an unusual twist
Purohit, Meena K.,Poduch, Ewa,Wei, Lianhu William,Crandall, Ian Edward,To, Terrence,Kain, Kevin C.,Pai, Emil F.,Kotra, Lakshmi P.
, p. 9988 - 9997 (2013/01/16)
Orotidine-5′-monophosphate decarboxylase (ODCase) is an interesting enzyme with an unusual catalytic activity and a potential drug target in Plasmodium falciparum, which causes malaria. ODCase has been shown to exhibit unusual and interesting interactions with a variety of nucleotide ligands. Cytidine-5′-monophosphate (CMP) is a poor ligand of ODCase, and CMP binds to the active site of ODCase with an unusual orientation and conformation. We designed N3- and N4-modified CMP derivatives as novel ligands to ODCase. These novel CMP derivatives and their corresponding nucleosides were evaluated against Plasmodium falciparum ODCase and parasitic cultures, respectively. These derivatives exhibited improved inhibition of the enzyme catalytic activity, displayed interesting binding conformations and unusual molecular rearrangements of the ligands. These findings with the modified CMP nucleotides underscored the potential of transformation of poor ligands to ODCase into novel inhibitors of this drug target.
A new and efficient synthetic method for 15N3-labeled cytosine nucleosides: Dimroth rearrangement of cytidine N3-oxides
Sako, Magoichi,Kawada, Hiroyoshi
, p. 8148 - 8150 (2007/10/03)
The treatment of 15N4-labeled cytidine N 3-oxide and 15N4-labeled 2′-deoxycytidine N3-oxide, prepared from the appropriate unprotected uridines in three reaction steps, with benzyl bromide in the presence of excess lithium methoxide allowed the smooth occurrence of their Dimroth rearrangement even under mild conditions leading to the corresponding 15N 3-labeled uridine 4-O-benzyloximes which can easily undergo the reductive N-O bond cleavage to give the desirable 15N 3-labeled cytosine nucleosides in high total yields.
AN IMPROVED PROCEDURE FOR THE PREPARATION OF AROMATIC HETEROCYCLIC N-OXIDES
Rhie, Soo Young,Ryu, Eung K.
, p. 323 - 328 (2007/10/03)
An improved procedure for the preparation of aromatic heterocyclic N-oxide is described.Nitrogen containing heterocyclic compounds gave their N-oxides in excellent yields by the reaction of m-CPBA in DMF/MeOH in the presence of HF in a short time under mild reaction conditions.The presence of HF and MeOH is crucial for the reaction.
Oxidation of Cytosine and 5-Methylcytosine Nucleosides and 5-Methyl-2'-deoxycytidine 5'-Monophosphate with Peroxosulfate Ions
Itahara, Toshio
, p. 1591 - 1594 (2007/10/02)
Reaction of 5-methylcytosine nucleosides and nucleotide with Na2S2O8 resulted in an oxidation of the 5-methyl group, while treatment of them and cytosine nucleosides with KHSO5 gave the corresponding N3-oxides.
3-HYDROXYURIDINE, AN ALLELOPATHIC FACTOR OF AN AFRICAN TREE, BAILLONELLA TOXISPERMA
Ohigashi, Hajime,Kaji, Mikio,Sakaki, Masaharu,Koshimizu, Koichi
, p. 1365 - 1368 (2007/10/02)
A plant growth inhibitor was isolated from Baillonella toxisperma, a plant which may cause an allelopathic effect in the tropical rain forest of Cameroon.From spectral and chemical evidence, the inhibitor was identified as 3-hydroxyuridine.It inhibited both hypocotyl and root growth of cucumber and radish seedlings, and also inhibited root growth of rice seedlings, but not sheath growth.The foliar treatment of 3-hydroxdyuridine exhibited inhibitory effects on the growth of a wide variety of weeds; however, it was quite ineffective against the growth of the crop plant, Zea mays.The strong plant growth inhibitory activity, together with the occurence in most parts of the tree at high levels, indicated that 3-hydroxyuridine may involved in the allelopathy of the tree. - Keywords: Baillonella toxisperma; Sapotaceae; allelopathy; allelochemical; 3-hydroxyuridine; plant growth inhibitor; herbicidal activity.
