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Synthesis and Bioactivity of New Analogue of Bicyclic 1‐Azafagomine
Author(s) -
Akhundova Fidan N.,
Kurbanova Malahat M.,
Huseynzada Alakbar E.,
Alves Maria J.,
Sujayev Afsun R.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903190
Subject(s) - bicyclic molecule , cycloaddition , pyridazine , chemistry , catalysis , methanol , bacteria , combinatorial chemistry , derivative (finance) , stereochemistry , double bond , medicinal chemistry , organic chemistry , biology , financial economics , economics , genetics
New ( S )‐(1,2,3,6‐tetrahydropyridazin‐3‐yl)methanol was synthesized by Lewis acid catalyzed and self‐assembled Diels‐Alder (LACASA‐DA) cycloaddition reaction using (S)‐BINOL as a chiral inductor. The N‐2 pyridazine position was protected, the hydroxyl group was carbonylated to form the new bicyclic structure. The protective group was removed and the double bond was dihydroxylated leading to the target compound. Removal of the protective group was performed using a newly found ecofriendly catalyst for N‐Boc deprotection. The final iminosugar derivative 7 and all newly synthesized intermediates, were investigated against S. aureus and E. coli bacteria and were found to show promising activity against both gram‐positive and gram‐negative bacteria.