246510-70-3

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(methylsulfonyl)oxy]methyl]-, phenylmethyl ester, (3S,4S)-
• Synonyms: benzyl(3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate;benzyl (3S,4S)-3-[(tert-butoxycarbonyl)amino]-4- {[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate;Benzyl (3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate
• CAS NO: 246510-70-3
• Molecular Formula: C19H28N2O7S
• Molecular Weight: 428.507
• Mol File: 246510-70-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(methylsulfonyl)oxy]methyl]-, phenylmethyl ester, (3S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(methylsulfonyl)oxy]methyl]-, phenylmethyl ester, (3S,4S)-(246510-70-3)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(methylsulfonyl)oxy]methyl]-, phenylmethyl ester, (3S,4S)-(246510-70-3)

Safety Data

• Hazardous Substances Data: 246510-70-3(Hazardous Substances Data)

Upstream product

• 569682-60-6 benzyl N-(2,2-dimethoxyethyl)-N-(prop-2-en-1-yl)carbamate 
• 114790-39-5 benzyl N-(2,2-dimethoxyethyl)carbamate 
• 501-53-1 benzyl chloroformate 
• 252770-03-9 Benzyl (4aS,7aS)-2,2-dimethylhexahydropyrrolo[3,4-d][1,3]oxazine-6(4H)-carboxylate (R)-mandelate 
• 252770-09-5 benzyl (cis)-3-amino-4-(hydroxymethyl)-1-pyrrolidinecarboxylate 
• 370880-75-4 benzyl N-(2-oxoethyl)-N-(prop-2-en-1-yl)carbamate 
• 246510-69-0 benzyl (3S,4S)-3-tert-butoxycarbonylamino-4-hydroxymethyl-pyrrolidine-1-carboxylate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 799279-83-7 benzyl (3S,4S)-3-(amino)-4-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate trifluoroacetate 
• 1056999-65-5 benzyl (3S,4S)-3-(amino)-4-{[chloro methyl]}-1-pyrrolidinecarboxylate hydrochloride 
• 799279-81-5 (1R,5S)-tert-butyl 3,6-diaza-bicyclo[3.2.0]heptane-6-carboxylate 
• 799279-84-8 (1R,5S)-3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate 
• 799279-80-4 Sofinicline 
• 370881-43-9 benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylate 

Relevant articles and documents

Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel α4β2 nicotinic acetylcholine receptor selective agonists

A series of novel, potent neuronal nicotinic acetylcholine receptor (nAChR) ligands derived from 3,6-diazabicyclo[3.2.0]heptane have been synthesized and evaluated for binding affinity and agonist activity at the α4β2 nAChR subtype. Structure-activity relationship studies of these novel nAChR ligands focused on substitution effects on the pyridine ring, as well as stereo- and regiochemical influences of the 3,6-diazabicyclo[3.2.0]heptane core. Small 5-substituents on the pyridine ring had a modest impact on the binding affinities and functional activities. 6-Bromo, 6-chloro, and 6-methyl substituents on the pyridine ring led to increased binding affinities and improved functional activities. Most of the 6-N-pyridinyl-substituted 3,6-diazabicyclo[3.2.0]heptanes are selective for the α4β2 nAChR subtype. Compounds (1R,5S)-25, (1R,5S)-55, and (1R,5S)-56 were virtually inactive as agonists at the hα3β4 nAChR but retained potency and efficacy at the hα4β2 nAChR subtype. 3-N-Pyridinyl-substituted series demonstrated more complex SAR. (1R,5R)-39, (1R,5R)-41, and (1R,5R)-42 were found to be much more potent at the hα3β4 nAChR subtype, whereas (1R,5R)-38 and (1R,5R)-40 were very selective at the hα4β2 nAChR subtype. The SAR studies of these novel ligands led to the discovery of several compounds with interesting in vitro pharmacological profiles.

Substituted diazabicycloakane derivatives

Compounds of formula (I) Z-Ar1—Ar2??(I) wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from an unsubstituted or substituted 5-membered heteroaryl ring; an unsubstituted or substituted 6-membered heteroaryl ring; 3,4-(methylenedioxy)phenyl; and phenyl 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.

(1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent

The present invention discloses (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane, salts thereof, and its use to treat pain and other disorders associated with the nicotinic acetylcholine receptor.