Synthetic studies of fluorinated analogues of 1-azafagomine: Remarkable nucleophilic substitution of fluorine by hydrazine

Autor:	I. Thomsen, Mikael Bols, Bettina V. Ernholt
Rok vydání:	1997
Předmět:	chemistry.chemical_compound Chemistry Stereochemistry Hydrogen bond Organic Chemistry Drug Discovery Hydrazine Fluorine Nucleophilic substitution Glycosidase inhibitor chemistry.chemical_element 1-azafagomine Biochemistry
Zdroj:	Tetrahedron. 53:9357-9364
ISSN:	0040-4020
Popis:	(±)-5-fluoro-4-hydroxy-3-hydroxymethylhexahydropyridazine (7) and some other azafagomine analogues were synthesis ed with the aim of comparing their glycosidase inhibition to that of (±)-4,5-dihydroxy-3-hydroxymethylhexahydropyridazine (1-azafagomine). Both in the synthesis of 7 and in the attempted synthesis of 4,5-dihydroxy-3-fluoromethylhexahydropyridazine, a remarkable degree of nucleophilic substitution of fluorine by hydrazine was observed in the final deprotection step involving hydrazinolysis. Fluorine analogue 7 was a considerably weaker glycosidase inhibitor than 1, suggesting that the 3-OH of 1 play a role in its binding by acting as a hydrogen bond donator.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5bbb11b966f1016331c3a89631430abb https://doi.org/10.1016/s0040-4020(97)00588-7 Zobrazit plný text záznamu Full Text from ScienceDirect