2038-40-6

Upstream product

• 552-70-5 pseudopelletierine 
• 64-17-5 ethanol 
• 552-70-5 granatan-3-one 
• 32752-52-6 1-(N-methyl)-1,5-pentanediamine 

Downstream Products

• 22143-89-1 (+/-)-Tropoyl granatan-3a-ol 
• 854733-35-0 3endo-hydroxy-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid 
• 552-70-5 pseudopelletierine 
• 504-12-1 exo-9-azabicyclo[3.3.1]nonan-3-ol 
• 6376-00-7 exo-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol 

Relevant academic research and scientific papers

Substrate Conformation Correlates with the Outcome of Hyoscyamine 6β-Hydroxylase Catalyzed Oxidation Reactions

Hyoscyamine 6β-hydroxylase (H6H) is an α-ketoglutarate dependent mononuclear nonheme iron enzyme that catalyzes C6-hydroxylation of hyoscyamine and oxidative cyclization of the resulting product to give the oxirane natural product scopolamine. Herein, the chemistry of H6H is investigated using hyoscyamine derivatives with modifications at the C6 or C7 position as well as substrate analogues possessing a 9-azabicyclo[3.3.1]nonane core. Results indicate that hydroxyl rebound is unlikely to take place during the cyclization reaction and that the hydroxylase versus oxidative cyclase activity of H6H is correlated with the presence of an exo-hydroxy group having syn-periplanar geometry with respect to the adjacent H atom to be abstracted.

TETRAAZA-CYCLOPENTA[A]INDENYL DERIVATIVES

The present invention provides compounds of Formula (I) as M1 receptor positive allosteric modulators for the treatment of diseases mediated by the muscarinic M1 mediator.

Tetraaza-cyclopenta[a]indenyl derivatives

The present invention provides compounds of Formula (I) as M1 receptor positive allosteric modulators for the treatment of diseases mediated by the muscarinic M1 mediator.

Determination of the N-methyl stereochemistry in tropane and granatane derivatives in solution: A computational and NMR spectroscopic study

Tropane (8-methyl-8-azabicyclo[3.2.1]octane) and granatane (9-methyl-9-azabicyclo[3.3.1]nonane) derivatives undergo fast N-methyl inversion. The distribution of axial and equatorial N-methyl invertomers of protonated and free amine forms in aqueous and methanol solutions was studied by room and low temperature NMR spectroscopy on tropinone, tropine, granatan-3-one (pseudopelletierine or pseudopelletrierin) and α-granatan-3-ol. Theoretical (DFT) distributions in both gas phase and solutions are also reported. Applicability of the computational model for the studied system was verified by comparison with invertomer distributions inferred from inverse-gated 13C NMR experiments. Among the tested functionals, the BH&HLYP/cc-pVDZ method yields the best agreement with experiment. Moreover, accounting for orbital relaxation upon immersion in the solution was found to be of importance in order to properly reproduce observed distributions.

FUSED BICYCLOHETEROCYCLE SUBSTITUTED AZABICYCLIC ALKANE DERIVATIVES

The invention relates to fused bicycloheterocycle substituted azabicyclic alkane derivatives, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

9-AZABICYCLO [3 . 3 . 1] NONANE DERIVATIVES AS MONOAMINE REUPTAKE INHIBITORS

The present invention relates to a 9-azabicyclo[3.3.1]nonane derivative of formula (I), wherein R1 is H or C1-5alkyl; X is O or NR2, wherein R2 is H, C1-5alkyl or C2-5acyl and Ar is C6-10aryl or a 5-10 membered heteroaryl ring system, both being optionally substituted with one to three of R3-R5 independently selected from halogen, C1-5alkyl, C1-5alkoxy, C3-6cycloalkyl, C2-5alkenyl, C2-5alkynyl, CN, NO2, hydroxy, phenyl, phenoxy and phenylC1-2alkoxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein said phenyl, phenoxy and phenylC1-2alkoxy are optionally substituted with one to three substituents independently selected from halogen and methyl or two of R3-R5 at adjacent positions together form a methylenedioxy or propylene unit, with the proviso that the compounds exo-9-methyl-3-phenoxy-9-azabicyclo[3.3.1]nonane and N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1H indazole-5-amine are excluded, or a pharmaceutically acceptable salt or solvate thereof. The invention also relates to pharmaceutical compositions comprising said 9-azabicyclo[3.3.1]nonane derivatives and to their use in therapy.

NOVEL 9-AZA-BICYCLO[3.3.1]NONANE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS

This invention relates to novel 9-aza-bicyclo[3.3.1]nonane 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 compositio

Metabolism of N-alkyldiamines and N-alkylnortropinones by transformed root cultures of Nicotiana and Brugmansia

A range of analogues of N-methylputrescine and tropinone were fed to transformed root cultures of Nicotiana rustica and/or a Brugmansia candida x aurea hybrid. These cultures were made by the transformation of the relevant plant species with Agrobacterium rhizogenes. A number of the metabolites, notably those showing a relatively modest alteration in the N-alkyl substituent, were metabolized in vivo to form homologues of the normal alkaloids biosynthesized by these roots. These products were identified by GC/MS and comparison with some synthetic reference materials. Analogues with major alterations in the size of the N-alkyl substituent were not metabolized at all. In the N. rustica cultures, the analogues fed at 1 mM significantly affected the profile of normal alkaloids, with up to a 4-fold diminution in nicotine being found in the presence of N-n-propylputrescine. The ratio between alkaloids of the pyrrolidine series and the piperideine series was also affected. In contrast, the presence of the analogues in the B. candida x aurea hybrid culture at 1 mM did not inhibit or substantially interfere with the accumulation of the normal spectrum of alkaloids. The potential for using these cultures to make complex novel products from simple precursors is discussed.