205993-51-7

Usage

Uses

Used in Organic Synthesis:
(RS)-Boc-Pip-BZA is used as an intermediate in the synthesis of various organic compounds due to its unique structure and the presence of the Boc-protected piperazine and benzotriazole groups.
Used in Pharmaceutical Industry:
(RS)-Boc-Pip-BZA is used as a building block for the development of new pharmaceutical compounds, particularly those targeting the central nervous system, as piperazine is a common structural element in many psychoactive drugs.
Used in Materials Science:
(RS)-Boc-Pip-BZA may be utilized in the development of novel materials with specific properties, such as those with enhanced thermal stability or chemical resistance, due to the presence of the Boc-protected piperazine and benzotriazole groups.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 100-46-9 benzylamine 
• 4043-87-2 pipecolic Acid 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Relevant academic research and scientific papers

Amino acid derivatives with anticonvulsant activity

A series of benzylamides of N-alkylated, N-acylated or free nine cyclic and one linear amino acids as potential anticonvulsants have been synthesized. The structures of the obtained compounds were designed on the basis of the previously determined structure and physicochemical properties/anticvonvulsant activity relationship of the formerly synthesized compounds of this type. The obtained compounds were evaluated in mice after intraperitoneal (ip) administration, by maximal electroshock seizure test (MES test), subcutaneous (sc) pentylenetetrazol test (sc PTZ test) and by the rotarod neurotoxicity test (Tox test). The results were the basis for their classification into one of three classes of the Anticonvulsant Screening Project (ASP) of the Antiepileptic Drug Development Program (ADDP) of the NIH. Three selected compounds were tested quantitatively in rats after oral administration. The MES ED50, sc PTZ ED50, Tox TD50 were determined and their protective index (PI) values were calculated. Anticonvulsant activity of the most promising compound (15) was examined in different seizure models. The respective ED50 and PI values of this compound were as follows: against bicuculline, 73 and 1.4; against PTZ, 47 and 2.2; against strychnine, 73 and 1.4; against pilocarpine 156, and 0.7; against kainic acid (2-carboxy-4-isopropenyl-3-pyrrolidineacetic acid), 39 and 2.6; against AMPA (α-amino-3-hydroxy-5methyl-4-isoxazolepropionic acid), 10 and 10.3 and against NMDA (N-methyl-D-Aspartic acid), 114 and 0.9.

Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2- piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6- dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 anal 34 led to a decrease in the MES activity. In the N-(α-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the α- position of the N-(α-methylbenzyl) group does not significantly affect MES activity.