Desformilflustrabromin

Desformilflustrabromin
IUPAC ime
	2-[6-bromo-2-(2-metilbut-3-en-2-il)-1H-indol-3-il]-N-metiletanamin
Identifikatori
CAS broj	474657-72-2
ATC kod	none
PubChem	CID 637026
ChemSpider	552693
Hemijski podaci
Formula	C16H21BrN2
Molarna masa	321,254 g/mol
	SMILES C=CC(C)(C)c2nc1cc(Br)ccc1c2CCNC; ;
	InChI InChI=1S/C16H21BrN2/c1-5-16(2,3)15-13(8-9-18-4)12-7-6-11(17)10-14(12)19-15/h5-7,10,18-19H,1,8-9H2,2-4H3 ; Key:GQHSCJUTJKLZPX-UHFFFAOYSA-N ;

Desformilflustrabromin (dFBr) je triptaminski derivat koji je bio prvo izolovan kao aktivni metabolit morske mahovine Flustra foliacea.^[1]

Bioaktivnost

Utvrđeno je da dFBr deluje kao pozitivni alosterni modulator neuronskog nikotinskog acetilholinskog receptora sa podtipnom specifičnošću za heteromerni receptor i bez uticaja na homomerne podtipove.^[2] Jedna nedavno objavljena studija je opisala sintezu u vodi rastvornih soli dFBr i potvrdila da one deluju kao selektivni potencijatori α4β2 nikotinskog acetilholinskog receptora koristeći dvoelektrodni metod.^[3] Poznato je da je dFBr citotoksičan na HCT-116 ćelijama ljudskog raka debelog creva.^[4]

Reference

^ Peters, Lars; Wright, Anthony D.; Kehraus, Stefan; Gündisch, Daniela; Tilotta, M. C.; König, Gabriele M. (2004). „Prenylated indole alkaloids from Flustra foliacea with subtype specific binding on NAChRs”. Planta Med. 70 (10): 883—6. PMID 15490312. doi:10.1055/s-2004-832610.
^ Sala, Francisco; Mulet, José; Reddy, Krishna P.; Bernal, José Antonio; Wikman, Philip; Valor, Luis Miguel; Peters, Lars; König, Gabriele M.; Criado, Manuel (2005). „Potentiation of human alpha4beta2 neuronal nicotinic receptors by a Flustra foliacea metabolite”. Neurosci. Lett. 373 (2): 144—9. PMID 15567570. doi:10.1016/j.neulet.2004.10.002.
^ Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A. (2007). „Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator”. Bioorganic and Medicinal Chemistry Letters. 17 (17): 4855—60. PMID 17604168. doi:10.1016/j.bmcl.2007.06.047.
^ Lysek, N; Rachor, E; Lindel, T (2002). „Isolation and structure elucidation of deformylflustrabromine from the North Sea bryozoan Flustra foliacea”. Z. Naturforsch., C, J. Biosci. 57 (11–12): 1056—61. PMID 12562094.

Spoljašnje veze

[1] Peters, Lars; Wright, Anthony D.; Kehraus, Stefan; Gündisch, Daniela; Tilotta, M. C.; König, Gabriele M. (2004). „Prenylated indole alkaloids from Flustra foliacea with subtype specific binding on NAChRs”. Planta Med. 70 (10): 883—6. PMID 15490312. doi:10.1055/s-2004-832610.

[2] Sala, Francisco; Mulet, José; Reddy, Krishna P.; Bernal, José Antonio; Wikman, Philip; Valor, Luis Miguel; Peters, Lars; König, Gabriele M.; Criado, Manuel (2005). „Potentiation of human alpha4beta2 neuronal nicotinic receptors by a Flustra foliacea metabolite”. Neurosci. Lett. 373 (2): 144—9. PMID 15567570. doi:10.1016/j.neulet.2004.10.002.

[3] Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A. (2007). „Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator”. Bioorganic and Medicinal Chemistry Letters. 17 (17): 4855—60. PMID 17604168. doi:10.1016/j.bmcl.2007.06.047.

[4] Lysek, N; Rachor, E; Lindel, T (2002). „Isolation and structure elucidation of deformylflustrabromine from the North Sea bryozoan Flustra foliacea”. Z. Naturforsch., C, J. Biosci. 57 (11–12): 1056—61. PMID 12562094.

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