55677-50-4Relevant academic research and scientific papers
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants
Geurts, Muriel,Poupaert, Jacques H.,Scriba, Gerhard K. E.,Lambert, Didier M.
, p. 24 - 30 (2007/10/03)
Glycine is a small neutral amino acid exhibiting weak anticonvulsant activities in vivo. Recently, studies have demonstrated that N- (benzyloxycarbonyl)glycine (1) antagonized seizures superior to glycine in addition to activity in the maximal electroshock (MES) test, a convulsive model where glycine is inactive. In the present study a series of ester and amide derivatives of 1 as well as esters of N-(3-phenylpropanoyl)glycine (5) have been prepared. The compounds were evaluated in the MES test as well as in several chemically induced seizure models. Among the derivatives investigated, N-(benzyloxycarbonyl)glycine benzylamide (16) was the most potent compound exhibiting an anticonvulsant activity in the MES test comparable to the drug phenytoin. Median effective doses (ED50) of 4.8 and 11.6 mg/kg were determined at 30 min and 3 h after ip administration, respectively. Compound 16 also effectively suppressed tonic seizures in different chemically induced models such as the strychnine, 3- mercaptopropionic acid, and pentylenetetrazole tests. Moreover, the compound studied here did not show acute neurotoxicity in the rotorod test up to a dose of 150 mg/kg. It is concluded that N-(benzyloxycarbonyl)glycine amides, especially 16, are potent anticonvulsant agents.
1-(o-NITROPHENYLSULPHONYLOXY)BENZOTRIAZOLE, REAGENT FOR THE CONDENSATION OF CARBOXYLIC ACIDS WITH AMINES
Topuzyan, V. O.,Martirosyan, M. S.
, p. 2148 - 2153 (2007/10/02)
With the Schotten-Baumann reaction we have synthesized 1-(o-nitrophenylsulfonyloxy)benzotriazole and have shown its suitability for the synthesis of esters of 1-hydroxybenzotriazole and carboxylic amides, and also of peptides.
Synthesis and Evaluation of 1- and 2-Substituted Fentanyl Analogues for Opioid Activity
Essawi, Mohamed Y.H.,Portoghese, Philip S.
, p. 348 - 352 (2007/10/02)
We synthesized fentanyl analogues that posses key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors.The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides.The synthesized compounds showed very week or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations.These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with diffrent subsites on either μ or δ receptors.Studies using the irreversible μ opioid receptor antagonist, β-funaltrexamine, indicate that fentanyl interacts preferentially with μ opioid receptors.
