Synthesis of derivatives of methoxydibenzo[b, f]oxepine in the presence of sodium azide

Hanna Krawczyk , Michał Wrzesiński , Damian Mielecki , Przemysław Szczeciński , Elżbieta Grzesiuk

Abstract

Dibenzo[b,f]oxepine is an important scaffold in medicinal chemistry and its derivatives occur in several medicinally important plants. A new approach to methoxydibenzo[b,f]oxepines (15e21) proceeding under mild reaction conditions, has been developed. Notably, the use of sodium azide in the reaction allows access to new substituted dibenzo[b,f]oxepines. In order to study their shape and conformation, the optimum structures of these compounds were calculated using the DFT B3LYP/6-311þþG(2d,p) method. A docking simulation was performed to insert compound 20 into the crystal structure of tubulin at the colchicine binding site to determine the probable binding model. The information from this work can be helpful for the investigation of new tubulin polymerization inhibitors exhibiting stronger activity.
Author Hanna Krawczyk ZChO
Hanna Krawczyk,,
- Department Of Organic Chemistry
, Michał Wrzesiński
Michał Wrzesiński,,
-
, Damian Mielecki
Damian Mielecki,,
-
, Przemysław Szczeciński ZChO
Przemysław Szczeciński,,
- Department Of Organic Chemistry
, Elżbieta Grzesiuk
Elżbieta Grzesiuk,,
-
Journal seriesTetrahedron, ISSN 0040-4020
Issue year2016
Vol72
No27-28
Pages3877-3884
Publication size in sheets0.5
Keywords in EnglishCyclization, Methoxydibenzo[b,f]oxepines, Heterocycles, DFT calculations, Molecular modeling
DOIDOI:10.1016/j.tet.2016.05.005
URL http://www.sciencedirect.com/science/article/pii/S0040402016303763
Languageen angielski
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publikacja2016-H.Krawczyk.pdf (file archived - login or check accessibility on faculty) publikacja2016-H.Krawczyk.pdf 1.22 MB
Score (nominal)30
ScoreMinisterial score = 30.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.651 (2) - 2016=2.429 (5)
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