57796-78-8Relevant academic research and scientific papers
Synthesis, antiviral and cytostatic activities, of carbocyclic nucleosides incorporating a modified cyclopentane ring. IV. Adenosine and uridine analogues
Nieto, M. Isabel,Caamano, Olga,Fernandez, Franco,Gomez, Maria,Balzarini, Jan,De Clercq, Erik
, p. 243 - 255 (2002)
Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.
Design, synthesis, and evaluation of antineoplastic activity of novel carbocyclic nucleosides
Helguera, Aliuska M.,Rodriguez-Borges,Caamano, Olga,Garcia-Mera, Xerardo,Gonzalez, Maykel Perez,Cordeiro, M. Natalia D.S.
, p. 213 - 231 (2010)
Cancer is the leading cause of death among men and women under age 85. Every year, millions of individuals are diagnosed with cancer. But finding new drugs is a complex, expensive, and very time-consuming task. Over the past decade, the cancer research co
Acyclic nucleosides bearing a furanyl scaffold
Nair, Vasu,Bera, Sanjib
, p. 37 - 43 (2005)
Synthesis of acyclic nucleosides bearing a furanyl scaffold is described. The approach involved the construction of the base moiety onto a dihydrofuranyl intermediate. While the A and C analogues did exhibit some substrate activity toward deoxycytidine ki
The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - An NMR and DFT study
Pohl, Radek,Rulisek, Lubomir,Rejman, Dominik
scheme or table, p. 423 - 430 (2011/11/14)
The mechanism of the decomposition of acryloylcarbamates 7a-b yielding highly reactive isocyanates 3a-b was proposed based on NMR measurements and quantum chemical calculations. A good agreement between the experimental kinetic data and DFT calculations allowed us to demonstrate that the stability of 7a-d depends on the presence of methyl in the acryloyl moiety and the position of the nitro group in the nitrophenolic part of the molecule. Furthermore, the reactivity of 7a-d with weakly nucleophilic and sterically hindered 2,4,6-tri-tert-butylaniline was explored by 1H NMR demonstrating the usefulness of reagents 7a-d offering access to a variety of 1-N-substituted uracils and thymines with potentially interesting biological properties. Copyright
Molecular recognition in the P2Y14 receptor: Probing the structurally permissive terminal sugar moiety of uridine-5′-diphosphoglucose
Ko, Hyojin,Das, Arijit,Carter, Rhonda L.,Fricks, Ingrid P.,Zhou, Yixing,Ivanov, Andrei A.,Melman, Artem,Joshi, Bhalchandra V.,Kovac, Pavol,Hajduch, Jan,Kirk, Kenneth L.,Harden, T. Kendall,Jacobson, Kenneth A.
experimental part, p. 5298 - 5311 (2009/12/04)
The P2Y14 receptor, a nucleotide signaling protein, is activated by uridine-5′-diphosphoglucose 1 and other uracil nucleotides. We have determined that the glucose moiety of 1 is the most structurally permissive region for designing analogues of this P2Y14 agonist. For example, the carboxylate group of uridine-5′-diphosphoglucuronic acid proved to be suitable for flexible substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y14 activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y14 potency. For example, the [5′′]ribose derivative had an EC50 of 0.24 μM. Selective monofluorination of the glucose moiety indicated a role for the 2′′- and 6′′-hydroxyl groups of 1 in receptor recognition. The β-glucoside was twofold less potent than the native α-isomer, but methylene replacement of the 1′′-oxygen abolished activity. Replacement of the ribose ring system with cyclopentyl or rigid bicyclo[3.1.0]hexane groups abolished activity. Uridine-5′-diphosphoglucose also activates the P2Y2 receptor, but the 2-thio analogue and several of the potent modified-glucose analogues were P2Y14-selective.
Synthesis of cyclopropanoid nucleoside analogues possessing a flexible side chain
Csuk, René,Kern, Anja
, p. 843 - 852 (2007/10/03)
A novel class of cyclopropanoic nucleoside analogues containing an hydroxyethyl residue instead of a hydroxymethyl side chain has been prepared in an easy sequence. These compounds showed weak antitumor activity. The resolution of the racemates on an analytical scale was performed by HPLC using chiral stationary phases.
Synthesis and antiviral studies of unsaturated analogues of isomeric dideoxynucleosides
Bera, Sanjib,Mickle, Travis,Nair, Vasu
, p. 2379 - 2395 (2007/10/03)
Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidin
Asymmetric total synthesis of (+)-carbocyclic uracil polyoxin C
Aggarwal, Varinder K.,Monteiro, Nuno
, p. 2531 - 2537 (2007/10/03)
A short, practical, asymmetric synthesis of carbocyclic uracil polyoxin C is described. The key step in the synthesis is a regio- and stereo-selective palladium-mediated substitution reaction of an α-amino substituted unsaturated lactone with bis-silylate
Synthesis of racemic carbocyclic cyclopropanoid nucleoside analogues
Csuk, Rene,Von Scholz, Yvonne
, p. 7193 - 7206 (2007/10/02)
As further representatives of a novel class of carbocyclic nucleoside analogues (±)-cis- and (±)-trans-(2-hydroxymethylcyclopropyl)-uracil, -thymine, and -inosine were synthesized from the corresponding dialkyl 1,2-cyclopropane dicarboxylates.
Synthesis of isonucleosides related to AZT and AZU
Purdy,Zintek,Nair
, p. 109 - 126 (2007/10/02)
Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5- methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.
