Synthesis And Properties Of Novel Polypyridyl Arylimidazoles Compounds

A series of new compounds, imidazo [4,5-f][1,10]-phenanthroline3（a^o） was synthesized from1,10-phenanthroline as the basic skeleton in the paper. The pharmacy activity and optical performancewere measured. The main content were as follows:Firstly, the simple and efficient synthetic strategy was designed.28compounds including13intermediates,15target produce and13new compounds were synthesized in this paper. It wasrelated to three aspects of the synthesis reaction as the following:1) The synthesis of the sevencontaining ferrocenyl, BINOL novel structure of2,2’-（ethane-1,2-dioxy）–diphenyl derivatives ofaromatic aldehyde1（a^g） were synthesized by the Reimer-Tiemann and Duff’s reaction.2) compound1,10-phenanthroline-5,6–dione was synthesized under the oxidation reaction with mixed acidwhile1,10–phenanthroline was the starting material.3) The imine was formed by1,10-phenanthroline-5,6–dione with the use of ammonium salt, then the imidazole ring was built bydehydration condensation with aromatic aldehydes, therefore we get fifteen imidazo[4,5-f][1,10]-phenanthroline3（a^o）.Secondly, in the aspect of pharmacological studies, through studing the15kinds of theabove-described synthesis target product’s use of inhibition to PTP1B for the first time, it turned out tobe that the compound3e,3i,3k,3l and3o’s effect of inhibition is the best,what’s more,theinhibitory concentrations can reach as high as84.56±1.78%. So it is the protein drugs of theinhibitors as for PTP1B, providing an important reference for the treatment of the modern typeâ…¡diabetes and obesity.In the aspect of optical performance, as1,10-phenanthroline substances have a goodphotoelectric performance, imidazole compounds also owned the proton so as that it can be easilyinfluenced by the external pH environment, this effect can be tested by fluorescence expressed. Basedon the two points above, testing15target products in the10different pH of a buffer solution of2.32,3.30,4.32,5.33,6.32,7.31,8.30,9.32,10.32and11.31for the first time, it turned that among which14compounds3a,3b,3c,3d,3e,3g,3h,3i,3J,3k,3l,3m,3n,3o showed a certain regularity as pHchanged, so in the acidic solution fluorescence intensity is raised gradually as the pH is enhanced, andit is raised gradually as the pH is weakened in an alkaline solution. As a conclusion, these kinds ofcompounds have the potential function as a fluorescent sensor materialof the pH.Lastly, studying the performance of the objective compound as a fluorescent sensor material ofthe metal ions for the first time. This paper selected15kinds of metal ions from both the main familyand vice family, such as Al³⁺, Pb²⁺, Ag+, Hg²⁺, Cr³⁺, Cu²⁺, Fe²⁺, Fe³⁺, Co²⁺, Mn²⁺, Ni²⁺, V4⁺, Na⁺, Ca²⁺,Zn²⁺, studying by the fluorescence test to find that the metal ions can make the target moleculeproduce a phenomenon which is called fluorescence quenching. According to the Stern-Volmerequation, the KSVof quenching coefficient is calculated. It turned out that the compounds3a for Fe²⁺,3b for Co²⁺and Cu²⁺,3e for Pb²⁺, Ag+and Mn²⁺,3h for Ni²⁺,3i for Cr³⁺,3m for Zn²⁺,3n for V4⁺, Hg²⁺,Al³⁺and Fe³⁺is the best in detetion, and finding that these compounds have potential fluorescencesensing functions of the metal ion.