116664-13-2Relevant academic research and scientific papers
Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization
Ragoussi, Maria-Eleni,Walker, Stephen M.,Piccanello, Andrea,Kariuki, Benson M.,Horton, Peter N.,Spencer, Neil,Snaith, John S.
supporting information; experimental part, p. 7347 - 7357 (2011/02/16)
A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2
Phosphodiester amidates of unsaturated nucleoside analogues: Synthesis and Anti-HIV activity
Winter, Holger,Maeda, Yosuke,Uchida, Hiroyuki,Mitsuya, Hiroaki,Zemlicka, Jiri
, p. 2191 - 2195 (2007/10/03)
The effect of introduction of a lipophilic phosphodiester amidate moiety on the HIV activity of inactive unsaturated nucleoside analogues was investigated. Phesphodiester alaninates 5a, 5b, and 6 derived from unsaturated nucleoside analogues 3b, 3c, and 4
Novel acyclic nucleotides and nucleoside 5'-triphosphates imitating 2',3'- dideoxy-2',3'-didehydronucleotides: Synthesis and biological properties
Shirokova,Tarussova,Shipitsin,Semizarov,Krayevsky
, p. 3739 - 3748 (2007/10/02)
A series of pyrophosphoryl (Z)-(phosphonomethoxy)but-2-enyl derivatives of pyrimidines and purines 9a-d and the corresponding phosphonates 10a-d were synthesized. The prepared compounds contain the phosphonate group as an α- phosphate mimic as well as an
Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds
Ashton,Canning Meurer,Cantone,Field,Hannah,Karkas,Liou,Patel,Perry,Wagner,Walton,Tolman
, p. 2304 - 2315 (2007/10/02)
A series of analogues of acyclovir and ganciclovir were prepared in which conformational constrainst were imposed by incorporation of a cyclopropane ring or unsaturation into the side chain. In addition, several related base-modified compounds were synthesized. These acyclonucleosides were evaluated for enzymatic phosphorylation and DNA polymerase inhibition in a staggered assay and for inhibitory activity against herpes simplex virus types 1 and 2 in vitro. Certain of the guanine or 8-azaguanine derivatives were good substrates for the viral thymidine kinase and were further converted to triphosphate, but none was a potent inhibitor of the viral DNA polymerase. Nevertheless, one member of this group, (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine (3a), displayed significant antiherpetic activity in vitro, superior to that of the corresponding cis olefin 4a. Another group, typified by (±)-9-[[(E)-2-(hydroxymethyl)cyclopropyl]methyl]adenine (17b), possessed modest antiviral activity despite an apparent inability to be enzymatically phosphorylated. The relationship of side-chain conformation and flexibility to biological activity in this series is discussed.
