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dc.contributor.authorBerezin, Andrey A.en
dc.contributor.authorKoutentis, Panayiotis Andreasen
dc.creatorBerezin, Andrey A.en
dc.creatorKoutentis, Panayiotis Andreasen
dc.date.accessioned2019-11-21T06:16:52Z
dc.date.available2019-11-21T06:16:52Z
dc.date.issued2011
dc.identifier.urihttp://gnosis.library.ucy.ac.cy/handle/7/55293
dc.description.abstractBoth 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.sourceTetrahedronen
dc.source.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-79955795617&doi=10.1016%2fj.tet.2011.04.003&partnerID=40&md5=319681f6ff01fda184bed75df4d5ab14
dc.subjectarticleen
dc.subjectpriority journalen
dc.subjectunclassified drugen
dc.subjectsynthesisen
dc.subject1,2 benzenediamineen
dc.subject1h 1,2,4 oxadiazolo[4,3 a]quinoxalin 1 oneen
dc.subject3,4 dihydroquinoxalin 2(1h) one oximeen
dc.subject8 (hydroxyphenyl) derivativeen
dc.subject8 bromo 4h [1,2,4]oxadiazolo[3,4 c][1,4] benzoxazin 1 oneen
dc.subjectcarbonyldiimidazoleen
dc.subjectchemical modificationen
dc.subjectchromatographyen
dc.subjectdemethylationen
dc.subjectguanylate cyclase inhibitoren
dc.subjectns 2028en
dc.subjectSuzuki Miyaura reactionen
dc.titleSuzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analoguesen
dc.typeinfo:eu-repo/semantics/article
dc.identifier.doi10.1016/j.tet.2011.04.003
dc.description.volume67
dc.description.issue22
dc.description.startingpage4069
dc.description.endingpage4078
dc.author.faculty002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences
dc.author.departmentΤμήμα Χημείας / Department of Chemistry
dc.type.uhtypeArticleen
dc.description.notes<p>Tradenames: ns 2028en
dc.description.notesCited By :3</p>en
dc.source.abbreviationTetrahedronen
dc.contributor.orcidKoutentis, Panayiotis Andreas [0000-0002-4652-7567]
dc.gnosis.orcid0000-0002-4652-7567


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