1,2,3-Triazoles Fused to Aromatic Rings

Synthesis, Optical Properties, and DNA Interaction of New Diquats Based on Triazolopyridines and Triazoloquinolines

“…The values of the reductionp otentialo ft hese molecules are in agreement with those registered for the originald iquat cation. [15] (100 mg, 0.51 mmol) was dissolved in 1,2-dibromoethane (1 mL, 11.6 mmol), and the solution was heated to 120 8Ci na no ven for 15 hu ntil ap recipitate formed. The compounds were able to interact with DNA either electrostatically or by intercalation.…”

“…Compound L3 presentsalower reduction potential owing to the conjugation of the aromatic rings that make the pyridine ring less electron deficient. The mixture was allowed to cool, washed with hot ethyl acetate ( 3) [15] (100 mg, 0.51 mmol) was dissolved in 1,3-dibromopropane (1 mL, 9.8 mmol), and the solution was heated to 120 8Ci na no ven for 15 h. The mixture was allowed to cool, washed with hot ethyl acetate ( 3), and decanted to give ay ellow powder.I solated yield:9 0%.M .p. Thermal denatura- Table 2.…”

“…The compounds were able to interact with DNA either electrostatically or by intercalation. = 244-245 8C; [15] (100 mg, 0.4 mmol) was dissolved in 1,2-dibromoethane (1 mL, 11.6 mmol), and the solution was heated to 120 8Ci na no ven for 15 h. The mixture was allowed to cool, washed with hot ethyl acetate ( 3), and decanted to give ay ellow powder was obtained. Variation in the meltingt emperature (DT m ), [a] measured as ad ifferenceb etween the free ct-DNA (58.2 AE 1 8Cfrom experimental data % 5 10 À5 m)a nd the ligand-bound ct-DNA, at different concentration ratios.…”

“…Thermal denatura- Table 2. [15] (100 mg, 0.4 mmol) was dissolved in 1,3-dibromopropane (1 mL, 9.8 mmol), and the solution was heated to 120 8Ci na no ven for 15 h. The mixture was allowed to cool, washed with hot ethyl acetate ( 3), and decanted to give ay ellow powder.I solated yield:9 3%.M .p. [b] Ligand r [b] 0. tion studies, UV/Visible spectroscopy,a nd fluorescencet itrations in the presence of ct-DNA werep erformed;t hus, the nature of the interaction with DNA was determined to be electrostatic for the PTP derivatives L1 and L2,and for the PTQ derivatives L3 and L4,b oth an electrostatic binding mode and intercalation were confirmed.…”

“…[8] Diquat is knownt oi nteract with DNA owing to its aromatic structure and dicationicc harge. [15] In fact, 3-(2'-pyridil)- [1,2,3]triazolo [1,5-a]pyridine( PTP) [16] has the same nitrogen atom disposition as 2,2'-bypiridine, which should permitc yclization with dialkyl halides. [14] An interesting way to achieve stronger intercalativei nteractions might be to replace the bypiridiner ings with condensed aromatic moieties.…”