18598-71-5Relevant 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Thalidomide (α-N-phthalimido-glutarimide), the withdrawn sedative compound, has recently been reemerged as a potent agent against epilepsy.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.
Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics
Mahindra, Amit,Sharma, Krishna K.,Rathore, Dinesh,Khan, Shabana. I.,Jacob, Melissa R.,Jain, Rahul
, p. 671 - 676 (2014/05/06)
In this communication, we report the design, synthesis and in vitro antimicrobial activity of ultra short peptidomimetics. Besides producing promising antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA), the dipeptidomimetics exhibited high antifungal activity against C. neoformans with IC50 values in the range of 0.16-19 μg mL-1. The most potent analogs exhibited 4-fold higher activity than the currently used drug amphotericin B, with no apparent cytotoxicity in a panel of mammalian cell lines. This journal is the Partner Organisations 2014.
Synthesis, characterization and biological evaluation of amino acid conjugates of mefenamic acid
Dubey, Nitin,Jain, Dinesh K.,Bhadoriya, Upendra S.,Solanki, Balvant
experimental part, p. 1237 - 1241 (2012/09/07)
Mefenamic acid is used for its antipyretic, analgesic, antiinflammatory properties and also inhibits cyclooxygenase-1 and cyclooxygenase- 2 (COX-1 and COX-2) enzymes reversibly, which decreases production of pro-inflammatory prostaglandin precursors. Mefenamic acid suffers from the general side effects of non-steroidal antiinflammatory drugs, owing to presence of free carboxylic acid group. The study aimed to retard the adverse effects of gastrointestinal origin. Amino acid conjugates of mefenamic acid were synthesized by amidation with methyl esters of amino acids namely, phenylalanine, cysteine, glycine, lysine, arginine, valine, proline, serine, alanine and methionine. Synthesized conjugates were characterized by melting point, TLC, 1H NMR and mass spectroscopy. Synthesized conjugates were also evaluated for their analgesic and antiinflammatory activities. Comparable analgesic and anti-inflammatory activities were obtained as compared to mefenamic acid.
