Synthesis, Characterization And Properties Of Some Novel Asymmetric Triarylamines And Divalent Glycoclusters Containing Thioglycoside Moiety

1. Four asymmetric triarylamines (DMTPA, m-CH₃-DMTPA, p-CH₃-DMTPA and m-OCH₃-DMTPA) were synthesized by diarylamines and 3,5-dimethyl-iodobenzene as the starting materials using Ullmann reaction. They are new compounds except DMTPA. The structures of the target compounds were characterized by IR, 1H NMR and elemental analysis. The optical, electrochemical, and thermal properties were examined. The results indicated that the synthesized compounds emitted deep green fluorescence in solution, displayed reversible redox processes and exhibited a good thermal stability. The synthesized triarylamines are potential hole-transporting materials and green-light-emitting materials.2. Twenty novel divalent glycoclusters (TM-II-6a⁶j and TM-III-7a⁷j) containing thioglycoside moiety were synthesized by monosaccharide (glucose, galactose and mannose), bromine and acetic anhydride as the starting materials via a series of reactions. The structures were characterized by IR, NMR and HRMS. The NMR spectrum of representative compound TM-II-6g was investigated detailedly by 2D NMR technique. The C, H chemical shifts was assigned.The newly synthesized target compounds (TM-II-6a⁶j and TM-III-7a⁷j) were screened for their anticancer and antivirus activity. The assay results showed that TM-II-6e and TM-II-6g showed higher activities against liver cancer at 5μg/mL with the inhibitory rate of 67.05 % and 68.49 %, TM-II-6d and TM-II-6f were moderate (43.87 %⁴0.60 %). TM-III-7h exhibited weak inhibitory activity to lung cancer (29.90 %), and TM-III-7c was showed weak inhibitory activity to intestinal cancer (24.67 %). Among all newly synthesized target compounds (TM-II-6a⁶j and TM-III-7a⁷j), only TM-III-7j showed moderate activity against Cdc25B phosphatase at 20μg/mL with the inhibitory rate of 46.08±6.49 %. But all the newly synthesized target compounds (TM-II-6a⁶j and TM-III-7a⁷j) have no inhibitory activity to C-C chemokine receptor 5 (CCR5).3. In this study, the research results will provide a reliable basis to the design, synthesis, develop of the novel HTMs and glycocluster drugs.