923956-64-3

Usage

Uses

Used in Medicinal Chemistry:
(1S,6R)-8[(1R)-1-phenyl-ethyl]-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester is used as a potential candidate in medicinal chemistry for its unique structural features and stereochemistry, which may contribute to its interaction with biological targets and its potential as a pharmaceutical agent.
Used in Organic Synthesis:
In the field of organic synthesis, (1S,6R)-8[(1R)-1-phenyl-ethyl]-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester serves as a building block or intermediate in the synthesis of more complex organic molecules, taking advantage of its reactive functional groups and structural motifs.

Upstream product

• 848591-74-2 (3SR,4SR)-1-t-butyl 4-ethyl (cis)-3-{[(1R)-1-phenylethyl]amino}-1,4-piperidinedicarboxylate 
• 71233-25-5 ethyl 1-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylate 
• 848591-75-3 4-hydroxymethyl-3-((1R)-1-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 52763-21-0 ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 388108-67-6 5-[(1R)-1-phenyl-ethylamino]-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 
• 923956-59-6 (3S,4S)-4-hydroxymethyl-3-[(1R)-1-phenyl-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 923956-66-5 (1S,6R)-2,2,2-trifluoro-1-[8[(1R)-1-phenyl-ethyl]-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-ethanone 
• 851526-80-2 (1S,6R)-3,8-diaza-bicyclo[4.2.0]octane-8-carboxylic acid tert-butyl ester 
• 370881-96-2 (1S,6R)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of 3,8-diazabicyclo[4.2.0] octane ligands, potent nicotinic acetylcholine receptor agonists

A series of potent neuronal nicotinic acetylcholine receptor (nAChR) ligands based on a 3,8-diazabicyclo-[4.2.0]octane core have been synthesized and evaluated for affinity and agonist efficacy at the human high affinity nicotine recognition site (hα4β2) and in a rat model of persistent nociceptive pain (formalin model). Numerous analogs in this series exhibit picomolar affinity in radioligand binding assays and nanomolar agonist potency in functional assays, placing them among the most potent nAChR ligands known for the hα4β2 receptor. Several of the compounds reported in this study (i.e., 24, 25, 28, 30, 32, and 47) exhibit equivalent or greater affinity for the hα4β2 receptor relative to epibatidine, and like epibatidine, many exhibit robust analgesic efficacy in the rat formalin model of persistent pain.

Substituted diazabicycloalkane derivatives

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.