130606-00-7

Upstream product

• 4043-87-2 pipecolic Acid 
• 15862-86-9 piperidine-2-carboxylic acid hydrochloride 
• 130497-14-2 (+/-)-[(N-ethoxycarbonyl)piperidine]-2-carboxylic acid 

Downstream Products

• 130605-98-0 1-(2-piperidinylcarbonyl)pyrrolidine 
• 99552-32-6 pipecolic acid-2,4-xylidide 
• 115642-90-5 1-(2-Pyrrolidin-1-ylmethyl-piperidin-1-yl)-2-(3-trifluoromethyl-phenyl)-ethanone 
• 130497-43-7 2-(4-Nitro-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone 
• 115642-89-2 2-(3-Nitro-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone 
• 130497-48-2 2-(4-Cyclohexyl-phenyl)-1-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethanone 
• 128103-41-3 [3H]-BRL 52537 
• 100158-63-2 2-[(1-Pyrrolidinyl)methyl]piperidine 
• 60717-51-3 (2R,S)-2-dimethylaminomethyl piperidine 
• 130497-29-9 Piperidine-2-carboxylic acid dimethylamide 

Relevant academic research and scientific papers

Optical Control of a Delayed Rectifier and a Two-Pore Potassium Channel with a Photoswitchable Bupivacaine

Photoswitchable blockers of potassium channels can be used to optically control neuronal excitability and hold great promise for vision restoration. Here, we report a series of improved photoswitchable blockers that feature a new pharmacophore based on the local anesthetic bupivacaine. These azobupivacaines (ABs) enable optical control over the delayed rectifier channel Kv2.1. and target the two-pore domain potassium channel TREK-1. For the first time, we have identified a compound that blocks conductance in the dark and potentiates it upon illumination. Using light as a trigger, ABs efficiently and reversibly silence action potential firing of hippocampal neurons in acute mouse brain slices.

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.

(2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: Novel, highly selective κ opioid analgesics

This paper describes the synthesis and structure-activity relationships as κ opioid analgesics of a novel class of 1-(arylacetyl)-2-(aminomethyl)piperidine derivatives (8). The active conformation of the pharmacophore, with a torsional angle (N1C2C7N8) of 60°, was defined with computational studies and 1H NMR. A quantitative structure-activity relationship study of the arylacetic moiety substitution indicated that the presence of an electron-withdrawing and lipophilic substituent in para and/or meta positions is required for good analgesic activity and κ affinity. The lead compounds (2S)-1-[(3,4-dichlorophenyl)acetyl]-2-(pyrrolidin-1-ylmethyl) piperidine hydrochloride (14) and (2S)-1-[[4-(trifluoromethyl)phenyl]acetyl]-2-(pyrrolidin-1- ylmethyl)piperidine hydrochloride (21) are the most κ/μ selective (respectively 6500:1 and 4100:1) and among the most potent (K(i) κ 0.24 and 0.57 nM, respectively) κ ligands identified so far. In the mouse tail flick model of antinociception, compound 14 (ED50 = 0.05 mg/kg sc) was 25 times more potent than morphine and 16 times more potent than the standard κ ligand U-50488.