Ferruginine
Ferruginine-type diazine analogues show moderate affinity for the central alpha4beta2 and remarkably low affinity for the alpha7* nAChR subtypes.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
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Bioorg Med Chem. 2001 Oct;9(10):2683-91.
Synthesis and evaluation of diazine containing bioisosteres of (-)-ferruginine as ligands for nicotinic acetylcholine receptors.[Pubmed:
11557356]
In this structure-affinity relationship (SAFIR) study, the bioisosteric potential of diazines in the field of Ferruginine-type nAChR ligands was investigated.
METHODS AND RESULTS:
Novel enantiopure analogues of (-)-Ferruginine (3) such as 6-8 were synthesized utilizing enantiomerically pure N-protected (+)-2-tropanone 9 from the 'chiral pool' as versatile chiral building block and a palladium-catalyzed Stille cross-coupling of the tributylstannyl diazines 12, 14 and 16 with the vinyl triflate 11 of (+)-2-tropanone 9. The structures of the novel diazine analogues 6-8 of (-)-Ferruginine (3) were assigned on the basis of spectral data, that of ligand 7 being additionally verified by X-ray crystallography. The bioisosteric replacement of the acetyl moiety as structural part of the lead compound 3 with the pyridazine, pyrimidine and pyrazine nucleus resulted in ligands with high to moderate affinity for the central alpha4beta2 and remarkably low affinity for the alpha7* nAChR subtypes.
CONCLUSIONS:
Among the compounds synthesized and tested, 7 was the most active one with K(i)=3.7 nM (alpha4beta2). Compared with the lead 3, this value represents a 30-fold improvement in the affinity for the alpha4beta2 subtype combined with a substantially improved selectivity ratio between the alpha4beta2 and alpha7* subtypes.
J Org Chem. 2011 Apr 15;76(8):2694-700.
Total synthesis of (-)-cocaine and (-)-ferruginine.[Pubmed:
21391709 ]
METHODS AND RESULTS:
Total synthesis of tropane alkaloids (-)-cocaine and (-)-Ferruginine were accomplished in nine steps each and in 55% and 46% overall yields, respectively, starting from the known Betti base derivative (+)-(7aR,10R,12S)-10-(1H-benzotriazol-1-yl)-7a,8,9,10-tetrahydro-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine. In this novel route, RCM reaction and 1,3-dipolar cycloaddition were employed as key steps for the enantioselective construction of tropane skeleton and the regioselective introduction of 3-bromo-2-isoxazoline ring as masked cis-2,3-disubstituents.
CONCLUSIONS:
To obtain the desired precursor (2S,5R)-2-allyl-5-vinylpyrrolidine for RCM reaction, we developed a general and practical method for the preparation of enantiopure cis-2,5-disubstituted pyrrolidines bearing alkene- and/or alkyne-containing substituents. We also offered two highly efficient pathways for the conversion of the 3-bromo-2-isoxazoline ring into the desired cis-2,3-disubstituted groups in (-)-cocaine and (-)-Ferruginine.
Australian Journal of Chemistry,1979, 32(11): 2537 -2543.
Alkaloids of Darlingia ferruginea[Reference:
WebLink]
METHODS AND RESULTS:
Darlingia ferruginea J. F. Bailey contains the new tropane alkaloids ferrugine (2) and 3α-benzoyloxy-2α-hydroxybenzyltropane (4) as well as darlingine (1) and Ferruginine (3), which also occur in D. darlingiana.
