54725-48-3

Upstream product

• 65907-08-6 trop-6-ene-3endo-ol; hydrochloride 
• 51-34-3 scopolamine 
• 20513-09-1 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol 
• 183626-74-6 (αS)-α-(acetoxymethyl)benzeneacetyl chloride 
• 37504-67-9 (αS)-α-(acetoxymethyl)benzeneacetic acid 
• 235092-10-1 ethyl 3-endo-3-hydroxy-8-azabicyclo[3.3.1]oct-6-ene-8-carboxylate 
• 152612-85-6 scopolamine hydrobromide trihydrate 
• 20368-51-8 scopolamine hydrobromide 

Downstream Products

• 20513-09-1 (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol 
• 51-34-3 scopolamine 

Relevant academic research and scientific papers

FLUOROPHENYL SUBSTITUTED MUSCARINIC RECEPTOR LIGANDS WITH SELECTIVITY FOR M3 OVER M2

The present invention relates to fluorophenyl substituted muscarinic receptor ligands with selectivity for M3 over M2 and to the use of these compounds in the treatment of various diseases such as asthma, chronic obstructive pulmonary disease (COPD), bronchopulmonary dysplasia (BPD) and urinary incontinence.

Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna

(-)-Hyoscyamine, the enantiomerically pure form of atropine, and its derivative scopolamine are tropane alkaloids that are extensively used in medicine. Hyoscyamine 6β-hydroxylase (H6H, EC 1.14.11.11), a monomeric α-ketoglutarate dependent dioxygenase, converts (-)-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. In this study, H6H of Atropa belladonna (AbH6H) was cloned, heterologously expressed in Escherichia coli, purified and characterized. The catalytic efficiency of AbH6H, especially for the second oxidation, was found to be low, and this may be one of the reasons why Atropa belladonna produces less scopolamine than other species in the same family. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, was shown not to be an obligatory intermediate in the biosynthesis of scopolamine using purified AbH6H with an in vitro 18O labeling experiment. Moreover, the nitrogen atom in the tropane ring of (-)-hyoscyamine was found to play an important role in substrate recognition.

3 -ARYLOXY- 8 -AZA-BICYCLO [3.2.1.] OCT- 6- ENE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS

This invention relates to novel 8-aza-bicyclo[3.2.1]oct-6-ene derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical composi

Synthesis and nicotinic receptor activity of a hydroxylated tropane

(±)-3α-Hydroxy homoepibatidine 4 has been synthesized from the alkaloid scopolamine 5 and its properties as a nicotinic agonist assessed. While still binding strongly, the compound showed reduced agonist potency for the α4β2 nAChR compared with the parent compound epibatidine 1. Compound 4 also displayed generally similar binding and selectivity profiles at α4β2, α 2β4, α3β4, and α4β4 nAChR subtypes to those for nicotine.

Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate

The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin, involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).

Parallel modification of tropane alkaloids

Various tropane alkaloids have been prepared by structural modification of the readily available natural product, scopolamine 1. Reaction of isocyanates with 6,7-dehydrotropine 5 provided a number of urethanes 6a-e. Reductive amination of tropinone 7 and subsequent reaction with isocyanates provided ureas 9a-f. Mitsunobu inversion of the C-3 alcohol of tropine 10 afforded the epimeric ester 11.