444342-66-9

Upstream product

• 100-46-9 benzylamine 
• 21691-43-0 (R,S)-2-(N-benzyloxycarbonylamino)pentanoic acid 
• 760-78-1 2-aminopentanoic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 444342-65-8 (R,S)-N-benzyl 2-aminopentanamide 

Relevant academic research and scientific papers

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

Quantitative structure-activity relationship analysis of functionalized amino acid anticonvulsant agents using k nearest neighbor and simulated annealing PLS methods

We report the development of rigorously validated quantitative structure-activity relationship (QSAR), models for 48 chemically diverse functionalized amino acids with anticonvulsant activity. Two variable selection approaches, simulated annealing partial