15994-13-5Relevant academic research and scientific papers
Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides
Bruno, Elvira,Buemi, Maria Rosa,Di Fiore, Anna,De Luca, Laura,Ferro, Stefania,Angeli, Andrea,Cirilli, Roberto,Sadutto, Daniele,Alterio, Vincenzo,Monti, Simona Maria,Supuran, Claudiu T.,De Simone, Giuseppina,Gitto, Rosaria
, p. 4316 - 4326 (2017/06/05)
On the basis of X-ray crystallographic studies of the complex of hCA II with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3) (PDB code 4Z1J), a novel series of 4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides (23-33) wa
Synthesis and biological evaluation of some new β-lactam-triazole hybrids
Jarrahpour, Aliasghar,Shirvani, Pouria,Sinou, Véronique,Latour, Christine,Brunel, Jean M.
, p. 149 - 162 (2016/01/25)
A series of novel β-lactams was synthesized from different imines and a special ketene derived from N-endo-5-norbornene-2,3-dicarboxyloylglycine 1 via the [2 + 2] ketene imine cycloaddition. Then, β-lactams 3a-h were treated with 1-azido-4-nitrobenzene 4
In Vivo Evaluation of Selective Carbonic Anhydrase Inhibitors as Potential Anticonvulsant Agents
Bruno, Elvira,Buemi, Maria R.,De Luca, Laura,Ferro, Stefania,Monforte, Anna-Maria,Supuran, Claudiu T.,Vullo, Daniela,De Sarro, Giovambattista,Russo, Emilio,Gitto, Rosaria
supporting information, p. 1812 - 1818 (2016/09/09)
Epilepsy is a common neurological disorder caused by an imbalance between inhibitory and excitatory neurotransmission. It is well known that neuronal excitability is related to γ-aminobutyric acid (GABA)ergic depolarization. HCO3?-dependent depolarization can be suppressed by membrane-permeable inhibitors of carbonic anhydrase. We previously identified some isoquinoline sulfonamides as potent and selective inhibitors of the human carbonic anhydrase II and VII (hCA II and hCA VII) isoforms. Given that hCA II and hCA VII are specific isoforms involved in GABA-mediated neuronal excitation, we hypothesized that they could represent the biological target for the development of new anticonvulsant agents. Therefore, for selected isoquinoline sulfonamides, we preliminarily tested their ability to prevent audiogenic seizures in DBA/2 mice. All compounds were evaluated after intraperitoneal administration, and some of them proved to protect the mice against convulsions. Among this series of compounds, several derivatives showed combined in vivo efficacy with inhibitory effects toward the targeted carbonic anhydrases (i.e., hCA II and hCA VII). Specifically, the most interesting molecule was 1-(4-aminophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamide (6), which proved to be a more active and selective hCA VII inhibitor than the reference compound topiramate. Further studies to explore the in vivo pharmacokinetic profile of the most active compounds may help to provide insight into the future design of selective hCA VII inhibitors.
Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst
Wendlandt, Alison E.,Stahl, Shannon S.
supporting information, p. 506 - 512 (2014/01/23)
Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.
Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides
Gitto, Rosaria,Ferro, Stefania,Agnello, Stefano,De Luca, Laura,De Sarro, Giovanbattista,Russo, Emilio,Vullo, Daniela,Supuran, Claudiu T.,Chimirri, Alba
experimental part, p. 3659 - 3664 (2009/09/27)
In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) fo
