Cyclic Triimidazoles as Stabilizers for Gene Promoter and Human Telomeric DNA G‐Quadruplexes

Abstract

Dedicated to Professor Cesare Gennari on the occasion of his 70th birthday.The synthesis and characterization of a small series of cyclic triimidazole derivatives functionalized with methylated pyridine or guanidine moieties is reported. These compounds were tested for their ability to bind to G-quadruplexes from both telomeric and oncogene promoter sequences. Some of them exhibited high affinity and effective G-quadruplex-stabilizing properties. Overall, these compounds may represent useful leads for developing more potent and selective analogues.

Layered Ag(I), Cd(II) and Cu(I) Luminescent Coordination Polymers Assembled Through a Tri‐Pyridyl Cyclic Triimidazole Ligand

“…(4 py) 3 TT ligand was synthetized as reported in the literature. [18] All manipulations were performed under aerobic conditions unless standard Schlenk techniques were required.…”

Electrochemical Insight on the Nitrogen-Rich, Weakly Aromatic Cyclic Triimidazole Multifunctional System Expanded with Pyridine or Thiophene Terminals

“…BrTT, Br 2 TT, Br 3 TT, (4-Py)TT, (4-Py) 2 TT, (4-Py) 3 TT and (2-Th) Me 2 Im were prepared according to literature procedures [15,20,21,41].…”

“…A fascinating member of the triazine family is represented by triimidazo[1,2-a:1′,2′-c:1″,2″-e][1, 3,5]triazine or cyclic triimidazole (hereafter TT, Scheme 1) and its derivatives, which have recently gained increasing attention for their multifaceted properties spanning from photoluminescence to supramolecular chemistry and biological activity [14][15][16][17][18][19][20][21]. TT has been known since 1973 [22]; however, the tedious synthetic protocols for its isolation constituted a major impediment until a simple procedure for its preparation in good yields has been reported [23], allowing further investigations on its properties and reactivity.…”

“…Finally, very recently, based on the observation that triazinic functionalities are frequently used in the biological field, pyrene-substituted TT has been successfully tested for cellular and bacterial bioimaging [19] while cyclic triimidazole derivatives functionalized with methylated pyridines or guanidines moieties have shown high affinity to bind to G-quadruplexes from both telomeric and oncogene promoter sequences [20].…”

Synthesis of 3‐Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation

“…To date, only Stille and Suzuki coupling have been applied for the selective functionalization of 1 in its C‐3 position, but a substrate pre‐functionalization is still needed (Figure 2b). [12c] Given these evidences, the lack of procedures to carry out a direct and selective C−H functionalization of this intriguing heterocycle was brought to our attention. In recent years, in fact, the C−H activation and functionalization established its pivotal role for the synthesis of new C−C bonds [13] .…”