1.
Org Biomol Chem
; 11(30): 4930-4, 2013 Aug 14.
Article
in English
| MEDLINE
| ID: mdl-23824158
ABSTRACT
A transition metal free tandem two-step strategy has been developed involving hydrolysis of 2-chloro-3-alkynyl quinoxalines/pyrazines followed by in situ cyclization of the corresponding 2-hydroxy-3-alkynyl intermediates in a single pot leading to fused furo N-heterocycles as potential inhibitors of sirtuins. A representative compound showed promising pharmacological properties in vitro and in vivo.
Subject(s)
Embryo, Nonmammalian/drug effects , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/pharmacology , Sirtuins/antagonists & inhibitors , Animals , Cyclization , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemistry , Heterocyclic Compounds/chemistry , Hydrolysis , Models, Molecular , Molecular Structure , Pyrazines/chemistry , Quinoxalines/chemistry , Sirtuins/metabolism , Structure-Activity Relationship , Zebrafish/embryology
2.
Chem Commun (Camb)
; 49(56): 6268-70, 2013 Jul 18.
Article
in English
| MEDLINE
| ID: mdl-23732749
ABSTRACT
An unprecedented AlCl3-mediated method has been developed involving aromatic C-H bond addition to an alkyne and heteroarylation of an arene in a single pot leading to densely functionalized novel olefins, e.g. 2-(2,2-diarylvinyl)-3-arylquinoxalines, as potential inhibitors of sirtuins.