dc.contributor.author | Berezin, Andrey A. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.contributor.author | Manos, Manolis J. | en |
dc.creator | Berezin, Andrey A. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.creator | Manos, Manolis J. | 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/7/55295 | |
dc.description.abstract | Sulfur analogues of the soluble guanylate cyclase (sGC) inhibitor NS2028 1a are synthesized. Treating 8-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one oxime (6) with 1,1′-thiocarbonyldiimidazole (1.1 equiv) gave the carbamothioate 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazine-1-thione (3a) in 83% yield. Alternatively reacting NS2028 1a with P2S5 (0.5 equiv) affords the carbamothioate 3a in 80% yield. Similar treatment of 8-aryl substituted NS2028 analogues 1b-d with P2S5 gave the carbamothioates 3b-d in 64-91% yields. Although quite stable, the carbamothioates 3a-d could be thermally isomerized in the presence of Cu (10 mol %) to afford the thiocarbamates 4a-d in high yields. Interestingly, in the case of carbamothioate 3a Pd and In metals also facilitated the isomerization. Furthermore, treatment of the thiocarbamates 4a-d with P2S 5 (0.5 equiv) affords the carbamodithioates 5a-d in 72-89% yields. All new compounds are fully characterized including single crystal X-ray data for carbamothioate 3a and thiocarbamate 4a. Finally, a mechanism is proposed for the carbamothioate to thiocarbamate isomerization. © 2011 Elsevier Ltd. All rights reserved. | en |
dc.source | Tetrahedron | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-79959328743&doi=10.1016%2fj.tet.2011.05.071&partnerID=40&md5=13e88f1aee2d757b72eb0382f3e22f45 | |
dc.subject | article | en |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | drug synthesis | en |
dc.subject | structure analysis | en |
dc.subject | X ray analysis | en |
dc.subject | chemical reaction | en |
dc.subject | drug structure | en |
dc.subject | chemical modification | en |
dc.subject | ns 2028 | en |
dc.subject | 8 bromo 4h [1,2,4]oxadiazolo[3,4 c][1,4]benzoxazin 1 one | en |
dc.subject | 8 bromo 4h [1,2,4]oxadiazolo[3,4 c][1,4]benzoxazine 1 thione | en |
dc.subject | 8 bromo 4h [1,2,4]thiadiazolo[3,4 c][1,4]benzoxazin 1 one | en |
dc.subject | isomerization | en |
dc.subject | oxadiazole derivative | en |
dc.title | Synthesis of sulfur containing analogues of the soluble guanylate cyclase inhibitor 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one NS2028 | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1016/j.tet.2011.05.071 | |
dc.description.volume | 67 | |
dc.description.issue | 30 | |
dc.description.startingpage | 5437 | |
dc.description.endingpage | 5443 | |
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 :2</p> | en |
dc.source.abbreviation | Tetrahedron | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |