Chromophoric binaphthyl derivatives.
A short synthetic route is outlined, starting from bromo-BN derivatives, via halogen lithium exchange, subsequent Michael reaction with dimethylaminoacrolein, hydrolysis to the corresponding aldehyde, and final condensation with a benzothiazolium unit to produce a BN-pentamethinium system, which absorbs in the visible range around 450 nm. Enantiopure ligands show a decent Cotton effect in the CD spectrum. Preliminary data show potential of these compounds in the area of supramolecular chemistry (enantioselective recognition) and also for medicinal application (induction of apoptosis). [reaction: see text]
Bríza
Tomás
T
Department of Analytical Chemistry Technická 5, Institute of Chemical Technology, CZ-166 28, Prague 6, Czech Republic.
Kejík
Zdenĕk
Z
Vasek
Petr
P
Králová
Jarmila
J
Martásek
Pavel
P
Císarová
Ivana
I
Král
Vladimír
V
D017209:Apoptosis / Q000187:drug effects; D002384:Catalysis; D002942:Circular Dichroism; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D006842:Hydrocarbons, Brominated; D009281:Naphthalenes