Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors.
Bioorg Chem
; 76: 140-146, 2018 02.
Article
em En
| MEDLINE
| ID: mdl-29175585
ABSTRACT
4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oxazepinas
/
Sulfonamidas
/
Inibidores da Anidrase Carbônica
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article