Reference of 1-(Bromomethyl)-4-iodobenzene. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1-(Bromomethyl)-4-iodobenzene, is researched, Molecular C7H6BrI, CAS is 16004-15-2, about Regioselective approach to colchiceine tropolone ring functionalization at C(9) and C(10) yielding new anticancer hybrid derivatives containing heterocyclic structural motifs. Author is Pyta, Krystian; Skrzypczak, Natalia; Ruszkowski, Piotr; Bartl, Franz; Przybylski, Piotr.
The influence of base type, temperature and solvent on regioselective C(9)/C(10) “”click”” modifications within the tropolone ring of colchiceine I [ R = OH] was investigated. New ether derivatives bearing alkyne, azide, vinyl, or halide aryl groups enabled assembly of the alkaloid part with heterocycles or important biomols. such as saccharides, geldanamycin or AZT into hybrid scaffolds by dipolar cycloaddition (CuAAC) or Heck reaction. Compared to colchicine I = [ R = OCH3] or colchiceine I [ R = OH], ether congeners, as e.g. II [ R = but-2-enyl] [IC50s(3e) 0.9nM], showed improved or similar anticancer effects, whereby the bulkiness of the substituents and the substitution pattern of the tropolone proved to be essential. Biol. studies revealed that expand-ing the ether arms by terminal basic heterocycles as quinoline or pyridine, decreases the toxicity in HDFcells at high anticancer potency (IC50s 1-2nM). Docking of ether and hybrid derivatives into the colchicine pocket of αGTP/β tubulin dimers revealed a relationship between the favorable binding mode and the attractive anticancer potency.
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