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Chlorocarbonylsulfenyl chloride cyclizations towards piperidin-3-yl-oxathiazol-2-ones as potential covalent inhibitors of threonine proteases

التفاصيل البيبلوغرافية
العنوان: Chlorocarbonylsulfenyl chloride cyclizations towards piperidin-3-yl-oxathiazol-2-ones as potential covalent inhibitors of threonine proteases
المؤلفون: Ales Obreza, Katarina Grabrijan, Selmir Kadić, Fernando Juan de Lera Garrido, Izidor Sosič, Stanislav Gobec, Marko Jukič
المصدر: Acta Chimica Slovenica, Vol 64, Iss 4, Pp 771-781 (2017)
بيانات النشر: Slovenian Chemical Society, 2017.
سنة النشر: 2017
المجموعة: LCC:Chemistry
مصطلحات موضوعية: cyclization, amide dehydration, oxathiazole-2-one, threonine protease, covalent inhibitors, irreversible inhibition, Chemistry, QD1-999
الوصف: Using rescaffolding approach, we designed piperidine compounds decorated with an electrophilic oxathiazol-2-one moiety that is known to confer selectivity towards threonine proteases. Our efforts to prepare products according to the published procedures were not successful. Furthermore we identified major side products containing nitrile functional group, resulting from carboxamide dehydration. We systematically optimized reaction conditions towards our desired products to identify heating of carboxamides with chlorocarbonylsulfenyl chloride and sodium carbonate as base in dioxane at 100 °C. Our efforts culminated in the preparation of a small series of piperidin-3-yl-oxathiazol-2-ones that are suitable for further biological evaluation.
نوع الوثيقة: article
وصف الملف: electronic resource
اللغة: English
تدمد: 1318-0207
1580-3155
Relation: https://journals.matheo.si/index.php/ACSi/article/view/3883; https://doaj.org/toc/1318-0207; https://doaj.org/toc/1580-3155
DOI: 10.17344/acsi.2017.3883
URL الوصول: https://doaj.org/article/8d35d2c7795842f1ad7bb5a288d7f70e
رقم الأكسشن: edsdoj.8d35d2c7795842f1ad7bb5a288d7f70e
قاعدة البيانات: Directory of Open Access Journals
الوصف
تدمد:13180207
15803155
DOI:10.17344/acsi.2017.3883