dc.contributor.author | Berezin, Andrey A. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.creator | Berezin, Andrey A. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.date.accessioned | 2019-11-21T06:16:52Z | |
dc.date.available | 2019-11-21T06:16:52Z | |
dc.date.issued | 2011 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55293 | |
dc.description.abstract | Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1′-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised. © 2011 Elsevier Ltd. All rights reserved. | en |
dc.source | Tetrahedron | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-79955795617&doi=10.1016%2fj.tet.2011.04.003&partnerID=40&md5=319681f6ff01fda184bed75df4d5ab14 | |
dc.subject | article | en |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | synthesis | en |
dc.subject | 1,2 benzenediamine | en |
dc.subject | 1h 1,2,4 oxadiazolo[4,3 a]quinoxalin 1 one | en |
dc.subject | 3,4 dihydroquinoxalin 2(1h) one oxime | en |
dc.subject | 8 (hydroxyphenyl) derivative | en |
dc.subject | 8 bromo 4h [1,2,4]oxadiazolo[3,4 c][1,4] benzoxazin 1 one | en |
dc.subject | carbonyldiimidazole | en |
dc.subject | chemical modification | en |
dc.subject | chromatography | en |
dc.subject | demethylation | en |
dc.subject | guanylate cyclase inhibitor | en |
dc.subject | ns 2028 | en |
dc.subject | Suzuki Miyaura reaction | en |
dc.title | Suzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analogues | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1016/j.tet.2011.04.003 | |
dc.description.volume | 67 | |
dc.description.issue | 22 | |
dc.description.startingpage | 4069 | |
dc.description.endingpage | 4078 | |
dc.author.faculty | 002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Χημείας / Department of Chemistry | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Tradenames: ns 2028 | en |
dc.description.notes | Cited By :3</p> | en |
dc.source.abbreviation | Tetrahedron | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |