Syntheses And Applications Of Novel Troger’’s Bases?

The huge rigidity, V-shaped twisted configuration, C2-symmetry chirality and recent applicationsin molecular recognition, chiral ligands, chiral solvents, molecular bionics receptors, clathrate hosts and DNA probes of Tr?ger’s base(TB) derivatives enable themselves to become the research hot spot in organic chemistry, pharmaceutical chemistry, polymer chemistry again one hundred years later. To further enrich the structure type of TB derivatives and to broaden their applied scope, herein we designed and synthesized three series of novel TB derivatives and tested their luminance and bioactivity(anti-hepatoma and anti-bacterium).This dissertation is composed of five chapters:The first section reviewed the syntheses, properties and applications of TB derivatives and proposed the design idea and innovation point of the dissertation.In the second section, the huge steric hindrance of TB derivatives which can efficiently prevent the intermolecular stacking in solid state was used as design starting point. A series of new V-shaped aromatic ring-fused compounds with strong solid luminance have been synthesized via the cross-coupling reactions of TB-Br(or TB-I) and diphenylamine(or carbazole, phenothiazine). Meanwhile, rac-1a(2,8-dibromo-6H, 12H-5,11-methano-dibenzo[b,f][1,5]diazocine) with high reactivity was resoluted to give(+)-1a(ee% = 97%) under the optimizing condition for the further research on its application in chiral recognition and asymmetric catalysis.In the third section, the huge rigidity and V-shaped twisted configuration of TB derivatives which can efficiently prevent intermolecular fluorescence quench via preventing the intermolecular π-π close stacking was used as design starting point. Formyl- or cyano-substituted TB derivatives have been synthesized. The results of their solid fluorescence indicated that the products 10 and 11 have strong fluorescence emission(450-500 nm and 500-550 nm, blue-green and yellow-green light, respectively) in the solid state.In the fourth section, flavonoid and benzimidazole frameworks, two class of important pharmaceutical intermediates with many bioactivities were linked to formyl substituted TB to afford a series of new flavonoid-(or benzimidazole-) substituted TB derivatives.In the last section, the anti-hepatoma activity of all products was tested by MTT assay firstly. The results indicated that 3a, 3b, 3c, 4b, 12a1, 12b1, 12b2, 13b1, 14b2 and 15d1 exhibited good inhibition against human Hep G2 cell over 10% in low concentration(5 ug/m L). And the inhibition of these ten compounds increased with the concentration increase. The inhibition of 25 ug/m L of 12b1 and 12b2 was over 80% and the inhibition of 50 ug/m L of 12b1 and 13b1 was over 90%. These results indicated the significant potential of these products as anti-cancer lead compound. Subsequently, the anti-bacterial activity of all products against Pseudomonas aeruginosa, Staphylococcus. aureus, Escherichia.coli and Escherichia.coli-NMD-1 were also evaluated via MTT assay. The results showed that these compounds have no inhibition activity against these four strains.The structures of all products were confirmed by IR, NMR and HRMS.