Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 최선 | * |
dc.date.accessioned | 2018-12-07T16:30:41Z | - |
dc.date.available | 2018-12-07T16:30:41Z | - |
dc.date.issued | 2017 | * |
dc.identifier.issn | 0022-2623 | * |
dc.identifier.other | OAK-20674 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/247393 | - |
dc.description.abstract | Potent and selective A3 adenosine receptor (AR) agonists were identified by the replacement of 4′-oxo- or 4′-thionucleosides with bioisosteric selenium. Unlike previous agonists, 4′-seleno analogues preferred a glycosidic syn conformation and South sugar puckering, as shown in the X-ray crystal structure of 5′-N-methylcarbamoyl derivative 3p. Among the compounds tested, N6-3-iodobenzyl analogue 3d was found to be the most potent A3AR full agonist (Ki = 0.57 nM), which was ≥800- and 1900-fold selective for A1AR and A2AAR, respectively. In the N6-cycloalkyl series, 2-Cl analogues generally exhibited better hA3AR affinity than 2-H analogues, whereas 2-H > 2-Cl in the N6-3-halobenzyl series. N7 isomers 3t and 3u were much weaker in binding than corresponding N9 isomers, but compound 3t lacked A3AR activation, appearing to be a weak antagonist. 2-Cl-N6-3-iodobenzyl analogue 3p inhibited chemoattractant-induced migration of microglia/monocytes without inducing cell death at ≤50 μM. This suggests the potential for the development of 4′-selenonucleoside A3AR agonists as novel antistroke agents. © 2017 American Chemical Society. | * |
dc.description.sponsorship | National Research Foundation of Korea | * |
dc.language | English | * |
dc.publisher | American Chemical Society | * |
dc.title | N6-Substituted 5′-N-Methylcarbamoyl-4′-selenoadenosines as Potent and Selective A3 Adenosine Receptor Agonists with Unusual Sugar Puckering and Nucleobase Orientation | * |
dc.type | Article | * |
dc.relation.issue | 8 | * |
dc.relation.volume | 60 | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 3422 | * |
dc.relation.lastpage | 3437 | * |
dc.relation.journaltitle | Journal of Medicinal Chemistry | * |
dc.identifier.doi | 10.1021/acs.jmedchem.7b00241 | * |
dc.identifier.wosid | WOS:000400538900014 | * |
dc.identifier.scopusid | 2-s2.0-85018442134 | * |
dc.author.google | Yu J. | * |
dc.author.google | Zhao L.X. | * |
dc.author.google | Park J. | * |
dc.author.google | Lee H.W. | * |
dc.author.google | Sahu P.K. | * |
dc.author.google | Cui M. | * |
dc.author.google | Moss S.M. | * |
dc.author.google | Hammes E. | * |
dc.author.google | Warnick E. | * |
dc.author.google | Gao Z.-G. | * |
dc.author.google | Noh M. | * |
dc.author.google | Choi S. | * |
dc.author.google | Ahn H.-C. | * |
dc.author.google | Choi J. | * |
dc.author.google | Jacobson K.A. | * |
dc.author.google | Jeong L.S. | * |
dc.contributor.scopusid | 최선(8659831000) | * |
dc.date.modifydate | 20240305081003 | * |