286946-67-6

Basic information

• Product Name: 2,6-Diazabicyclo[3.2.1]octane-6-carboxylic acid, phenylmethyl ester
• CAS NO: 286946-67-6
• Molecular Formula: C14H18N2O2
• Molecular Weight: 246.309
• Mol File: 286946-67-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,6-Diazabicyclo[3.2.1]octane-6-carboxylic acid, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diazabicyclo[3.2.1]octane-6-carboxylic acid, phenylmethyl ester(286946-67-6)
• EPA Substance Registry System: 2,6-Diazabicyclo[3.2.1]octane-6-carboxylic acid, phenylmethyl ester(286946-67-6)

Safety Data

• Hazardous Substances Data: 286946-67-6(Hazardous Substances Data)

Upstream product

• 140927-13-5 benzyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 286946-90-5 benzyl 5-(hydroxyimino)-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 286946-66-5 benzyl 3-oxo-2,6-diazabicyclo[3.2.1]-octane-6-carboxylate 

Downstream Products

• 286946-68-7 benzyl 2-(6-chloro-3-pyridinyl)-2,6-diazabicyclo[3.2.1]octane-6-carboxylate 
• 286946-98-3 tert-butyl 2,6-diazabicyclo[3.2.1]octane-2-carboxylate 
• 1335145-67-9 ethyl 4-{6-[adamantan-1-ylmethyl]-2,6-diazabicyclo[3.2.1]oct-2-yl}benzoate 
• 1335145-66-8 ethyl 4-{6-[adamantan-1-ylcarbonyl]-2,6-diazabicyclo[3.2.1]oct-2-yl}benzoate 
• 1335145-65-7 ethyl 4-(2,6-diazabicyclo[3.2.1]octan-2-yl)benzoate 

Relevant articles and documents

Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)- bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds.

DIAZABICYCLIC DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS

Compounds of formula (I) or a pharmaceutically acceptable salt thereof wherein: V is selected from the group consisting of a covalent bond and CH2; W is selected from the group consisting of a covalent bond, CH2and CH2CH2; X is selected from the group consisting of a covalent bond and CH2; Y is selected from the group consisting of a covalent bond, CH2, and CH2CH2; Z is selected from the group consisting of CH2, CH2CH2, and CH2 CH2 CH2; L1is selected from the group consisting of a covalent bond and (CH2)n; n is 1-5; R1 is selected from the group consisting of (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), and (l); R2is selected from the group consisting of hydrogen, alkoxycarbonyl, alkyl, aminoalkyl, aminocarbonylalkyl, benzyloxycarbonyl, cyanoalkyl, dihydro-3-pyridinylcarbonyl, hydroxy, hydroxyalkyl, phenoxycarbonyl, and-NH2; are useful for controlling synaptic transmission in mammal.