title: Piloty's acid derivative with improved nitroxyl-releasing characteristics.
abstract: Recent studies have shown that nitroxyl (HNO) ((1)HNO/(3)NO(-)), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2-nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N-hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Aizawa
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Nakagawa
authors.forename: Kazuya
authors.initials: K
authors.lastname: Matsuo
authors.forename: Kodai
authors.initials: K
authors.lastname: Kawai
authors.forename: Naoya
authors.initials: N
authors.lastname: Ieda
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Suzuki
authors.forename: Naoki
authors.initials: N
authors.lastname: Miyata
mesh_terms: D001565:Benzoates / Q000737:chemistry; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000737:chemistry / Q000494:pharmacology; D009589:Nitrogen Oxides / Q000737:chemistry* / Q000494:pharmacology; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D001565:Benzoates; D006877:Hydroxamic Acids; D009589:Nitrogen Oxides; D013449:Sulfonamides; D009569:Nitric Oxide; C097220:Piloty's acid; C039900:nitroxyl