27462-45-9Relevant articles and documents
Synthesis, molecular docking, and antiepileptic activity of new N-phthaloylglycine derivatives
Amanlou, Arash,Amanlou, Massoud,Asadi, Mehdi,Hosseini, Faezeh Sadat,Khorasani, Reza,Moradkhani, Fatemeh,Morgani, Ahmadreza Barazesh,khademi, Mona
, (2022/01/19)
Thalidomide (α-N-phthalimido-glutarimide), the withdrawn sedative compound, has recently been reemerged as a potent agent against epilepsy. In this study, five l-amino acid derivatives of N-phthaloylglycine were synthesized and were tested on pentylenetetrazole (PTZ) induced seizure mice model. N-phthaloylglycine was prepared by reaction of phthalic anhydride and glycine in the presence of triethylamine in toluene under reflux. Arginine, glutamine, leucine, phenylalanine, and tryptophan methyl ester were prepared and coupled with N-phthaloylglycine using coupling agents (EDC and HOBt). The final compounds were characterized by spectroscopic methods (1H NMR, 13 CNMR, IR, and MS). A docking study using AutoDock 4.2 was performed to predict the possible interactions of synthesized compounds on the GABAA receptor. All compounds were characterized, docked into the binding pocket of the GABAA receptor, and tested on pentylenetetrazole-induced seizures in mice. As expected, in silico studies demonstrated that all compounds interact efficiently with the GABAA receptor. All synthesized compounds showed satisfactory results leading to increased latency time to the first symptom of a seizure. The phenylalanine methyl ester derivative of N-phthaloylglycine (6d) had antiepileptic effects even more potent than thalidomide. Increasing lipophilicity and facilitating compounds delivery through l-amino acid carriers to the brain appear to be responsible for the remarkable activity of these compounds. Both in silico and in vivo results suggest that the l-amino acid derivatives of N-phthaloylglycine act as a novel compound against chemically induced seizures through interaction with the binding pocket of the GABAA receptor.
BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS
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Page/Page column 48, (2012/09/10)
The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III: