Stereoselective and regioselective synthesis of azepane and azepine derivatives via piperidine ring expansion

2002 ◽  
pp. 2080-2086 ◽  
Author(s):  
Hyun-soon Chong ◽  
Bishwajit Ganguly ◽  
Grant A. Broker ◽  
Robin D. Rogers ◽  
Martin W. Brechbiel
Keyword(s):  
Ring Expansion ◽  
Regioselective Synthesis ◽  
Piperidine Ring

Stereoselective and Regioselective Synthesis of Azepane and Azepine Derivatives via Piperidine Ring Expansion.

ChemInform ◽  
2003 ◽  
Vol 34 (8) ◽  
Author(s):  
Hyun-soon Chong ◽  
Bishwajit Ganguly ◽  
Grant A. Broker ◽  
Robin D. Rogers ◽  
Martin W. Brechbiel
Keyword(s):  
Ring Expansion ◽  
Regioselective Synthesis ◽  
Piperidine Ring

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

2015 ◽  
Vol 13 (29) ◽  
pp. 7924-7927 ◽  
Author(s):  
Jiajia Yu ◽  
Huijun Zhao ◽  
Shuguang Liang ◽  
Xiaoguang Bao ◽  
Chen Zhu
Keyword(s):  
Ring Expansion ◽  
Regioselective Synthesis

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described.

scholarly journals Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 354 ◽  
Author(s):  
Cécile Baudoin-Dehoux ◽  
Tessa Castellan ◽  
Frédéric Rodriguez ◽  
Arnaud Rives ◽  
Fabien Stauffert ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Docking Study ◽  
Ring Expansion ◽  
Membered Ring ◽  
The Other ◽  
Piperidine Ring ◽  
Molecular Docking Study ◽  
Pharmacological Chaperone ◽  
Simple Ring ◽  
Selective Targeting

A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal β-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-alkyl piperidine isomers, non-cytotoxic and inactive regarding ceramide glucosylation, revealed to be potent inhibitors of GBA. A molecular docking study showed that the positions of the piperidine ring of the compound 6b and its analogous 2-O-heptyl DIX 8 were similar to that of isofagomine. Furthermore, compound 6b promoted mutant GBA enhancements over 3-fold equivalent to that of the related O-Hept DIX 8 belonging to one of the most potent iminosugar-based pharmacological chaperone series reported to date.

ChemInform Abstract: A Facile and Regioselective Synthesis of 1-Tetralones via Silver-Catalyzed Ring Expansion.

ChemInform ◽  
2015 ◽  
Vol 46 (46) ◽  
pp. no-no
Author(s):  
Jiajia Yu ◽  
Huijun Zhao ◽  
Shuguang Liang ◽  
Xiaoguang Bao ◽  
Chen Zhu
Keyword(s):  
Ring Expansion ◽  
Regioselective Synthesis
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