56217-93-7Relevant academic research and scientific papers
VIGABATRIN BIOISOTERES AND RELATED METHODS OF USE
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Page/Page column 8; 15, (2010/11/26)
Compounds bioisoteric to vigabatrin and related methods of use.
New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity
Yuan, Hai,Silverman, Richard B.
, p. 1331 - 1338 (2007/10/03)
A series of potential substrates of γ-aminobutyric acid aminotransferase (GABA-AT) with lipophilic bioisosteres of the carboxylic acid group (2-7) were synthesized and tested. Most of the synthesized compounds showed substrate activities with GABA-AT; 1H-tetrazole-5-propanamine (6) was the best of those tested. The potential time-dependent inhibitor of GABA-AT, 1H-tetrazole-5-(α-vinyl-propanamine) (8), was designed based on the structures of 6 and the antiepilepsy drug vigabatrin (4-aminohex-5-enoic acid, 1). The synthesized compound 8 showed time-dependent inhibition of GABA-AT, but its potency is lower than that of vigabatrin. Methylation of the tetrazole group in 8 resulted in loss of time-dependent activity, suggesting that the tetrazole ring, the carboxylate bioisostere, exists in its deprotonated form in the enzyme active site.
Efficient syntheses of 5-aminoalkyl-1H-tetrazoles and of polyamines incorporating tetrazole rings
Athanassopoulos, Constantinos M.,Garnelis, Thomas,Vahliotis, Dimitrios,Papaioannou, Dionissios
, p. 561 - 564 (2007/10/03)
(Chemical Equation Presented) Linear Nω-tritylated ω-amino thiobenzylamides and Nα,Nω- ditritylated polyamino mono- or bisthioamides were efficiently converted to the corresponding tetrazole derivatives upon treatment with
Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors
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Page 54, (2010/02/06)
Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR4═CR5—, —CR4═CR5—S—, —O—CR4═CR5—, —CR4═CR5—O—, —N═CR4—S—, —S—CR4═N—, —NR6—CR4═CR5— and —CR4═CR5—NR6—; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.
