Ferruginine

CAS# 73069-63-3

Ferruginine

Catalog No. BCN1911----Order now to get a substantial discount!

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Quality Control of Ferruginine

Number of papers citing our products

Chemical structure

Ferruginine

3D structure

Chemical Properties of Ferruginine

Cas No. 73069-63-3 SDF Download SDF
PubChem ID 10012258 Appearance Powder
Formula C10H15NO M.Wt 165.23
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-en-4-yl]ethanone
SMILES CC(=O)C1=CCC2CCC1N2C
Standard InChIKey KQIRSQYBYQBMIG-WPRPVWTQSA-N
Standard InChI InChI=1S/C10H15NO/c1-7(12)9-5-3-8-4-6-10(9)11(8)2/h5,8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Ferruginine

TargetsAChR

Ferruginine Dilution Calculator

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Ferruginine Molarity Calculator

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Preparing Stock Solutions of Ferruginine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.0522 mL 30.2608 mL 60.5217 mL 121.0434 mL 151.3042 mL
5 mM 1.2104 mL 6.0522 mL 12.1043 mL 24.2087 mL 30.2608 mL
10 mM 0.6052 mL 3.0261 mL 6.0522 mL 12.1043 mL 15.1304 mL
50 mM 0.121 mL 0.6052 mL 1.2104 mL 2.4209 mL 3.0261 mL
100 mM 0.0605 mL 0.3026 mL 0.6052 mL 1.2104 mL 1.513 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ferruginine

BF(3)-Induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (+/-)-ferruginine.[Pubmed:11112563]

J Org Chem. 2000 Dec 15;65(25):8454-7.

Total synthesis of the alkaloid (+/-)-Ferruginine (1) has been developed via the 2-phenylsulfonyl 1,3-diene approach. BF(3)-induced rearrangement of the N-protected cyclohexane aziridino cyclopropane 8, derived from its corresponding epoxy cyclopropane, afforded the desired tropane alkaloid skeleton 9 in good yield. Michael addition of nitroethane (as an acyl anion equivalent) and transformation of the nitro group of the adduct 10 to a keto function gave 11. Elimination of benzenesulfinic acid and subsequent replacement of the tosyl group by a methyl group afforded the title compound 1.

Total synthesis of (-)-cocaine and (-)-ferruginine.[Pubmed:21391709]

J Org Chem. 2011 Apr 15;76(8):2694-700.

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-na phtho[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. 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.

Synthesis and evaluation of diazine containing bioisosteres of (-)-ferruginine as ligands for nicotinic acetylcholine receptors.[Pubmed:11557356]

Bioorg Med Chem. 2001 Oct;9(10):2683-91.

In this structure-affinity relationship (SAFIR) study, the bioisosteric potential of diazines in the field of Ferruginine-type nAChR ligands was investigated. 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. 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.

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