Bisbenzimidazole to benzobisimidazole: from binding B-form duplex DNA to recognizing different modes of telomereG-quadruplex

Abstract

A bisbenzimidazole was discovered to bind helix DNA, while related benzobisimidazole derivatives were found to bind and induce different G-quadruplex isomers.

Design, synthesis and bioevaluation of novel candidate selective estrogen receptor modulators

“…Synthesis of compounds of series 3 is depicted in Scheme 2. 4-(Dialkylaminoethoxy)benzaldehydes (4aeh), synthesized from commercially available dialkylaminoethyl chloride (Scheme 1) [12] or from 4-hydroxybenzaldehyde, dibromoethane and dialkylamine (Scheme 2) [13], were reduced [14] to the corresponding benzyl alcohol 5aeh. Subsequent benzylation reaction [15] of 2-naphthol with these benzyl alcohols in the presence of boron trifluoride etherate resulted in formation of the desired 1-(4-(2-(dialkylamino) ethoxy)benzyl)naphthalen-2-ols (3aeh; Scheme 2).…”

Targeting G-quadruplex nucleic acids with heterocyclic alkaloids and their derivatives

“…Further biophysical experiments revealed that the electrostatic surface of M2 was similar to 307A and 12459 and plays an important role in end-stacking binding to the G-quadruplex [65]. The great bioactivity of these compounds has promoted the development of various types of similar compounds, such as pyrimidine linked bisaryl compounds [66], urea linked bis-phenyl compounds [67], bisphenanthrolines [68] and bis-benzimidazoles [69]. …”

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

“…A great number of 2‐substituted benzimidazoles have been synthesized and their biological activities reported (Figure ) . A number of these studies has also focused on symmetrical and unsymmetrically substituted bis‐benzimidazoles . Some of the bis‐benzimidazoles have found use in diagnostic and/or therapeutic applications such as Hoechst‐33258 and its series (Figure ) …”