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Desformylflustrabromine Hydrochloride is a positive allosteric modulator of α4β2 nicotinic acetylcholine receptors.

Upstream product

• 80693-54-5 N-{2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]ethyl}-N-methylformamide 
• 863885-34-1 N-{2-[2-(1,1-dimethylallyl)-1H-indol-3-yl]ethyl}-N-methylformamide 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 598-25-4 Dimethylallene 
• 54268-27-8 N^b-formyl-N^b-methyltryptamine 
• 55454-18-7 9-(3-methylbut-2-enyl)-9-borabicyclo[3.3.1.]nonane 
• 951322-09-1 tert-butyl 2-(6-bromo-2-(1,1-dimethylallyl)-1H-indol-3-yl)ethyl-N-methylcarbamate 
• 1353012-45-9 C₂₂H₁₉BrCo₂N₂O₆ 
• 52415-29-9 6-bromo-1H-indole 
• 209168-89-8 6-bromo-N₁₀-methyl-N₁₀-Boc-tryptamine 
• 209169-05-1 N-Methyl-6-bromotryptamine 

Relevant academic research and scientific papers

Total synthesis of flustramine C via dimethylallyl rearrangement

(Chemical Equation Presented) The marine natural product flustramine C from the bryozoan Flustra foliacea was synthesized in five steps and 38% yield starting from Nb-methyltryptamine. The key step is the biomimetic oxidation of the natural pro

Deconstruction of the α4β2 nicotinic acetylcholine receptor positive allosteric modulator desformylflustrabromine

Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of α4β2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for α4β2 versus α7 nACh receptors. Pharmacophoric features for the allosteric modulation of α4β2 nACh receptors by 1 were identified.

Concise synthesis of deformylflustrabromine, a marine indole alkaloid, through a 2-propynyl dicobalt hexacarbonyl complex

Deformylflustrabromine, a marine indole alkaloid, was synthesized from 6-bromotryptamine, a plausible biosynthetic precursor, without protection of the amino group by a two-step reverse prenylation involving the Nicholas reaction and reductive decomplexat

Study on the NBS-induced rearrangement of 2-tert-prenyltryptamines

Treatment of 2-tert-prenyltryptamines with N-bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert-prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3-b]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement. Georg Thieme Verlag Stuttgart - New York.

Synthesis of desformylflustrabromine and its evaluation as an α4β2 and α7 nACh receptor modulator

Desformylflustrabromine (dFBr; 1) and desformylflustrabromine-B (dFBr-B; 2) have been previously isolated from natural sources, and the former has been demonstrated to be a novel and selective positive allosteric modulator of α4β2 nicotinic acetylcholine (nACh) receptors. The present study describes the synthesis of water-soluble salts of 1 and 2, and confirms and further investigates the actions of 1 and 2 using two-electrode voltage clamp recordings.