Tridentate chelating agents containing pyridine rings were synthesized by click chemistry with alkyne (c) and azide (d) which are the derivatives of bis(pyridin-2-ylmethyl)amine. The cold labeling yields of the compounds synthesized by the three nitrogen atoms in these tridentate chelating agents and fac-[Re(CO)3(H2O)3]+ were more than 90 %, and the total yields were over 75 %, comparable to the yields of the compounds synthesized by fac-[Re(CO)3]+ and the tridentate chelating agents containing carboxyl, amino-group and nitrogen atom (N3) in the triazol ring which synthesized from 2-aminopent-4-ynoic acid were more than 90 % and 82 %. The tridentate chelating agents analogues which contain different pyridine rings and triazole compounds which contain amino and carboxyl could be potential radiolabeling ligands for fac-[188Re(CO)3(H2O)3] + as the bifunctional chelating agents.