Primary anti-proliferative activity evaluation of 1-(quinolizidin-1’-yl)methyl- and 1-( $$\omega $$ -tert-amino)alkyl-substituted 2-phenyl-, 2-benzyl- and 2-[(benzotriazol-1/2-yl)methyl]benzimidazoles on human cancer cell lines

Abstract

Twenty benzimidazole derivatives bearing in position 1 a ([Formula: see text]-tert-amino)alkyl chain (mainly quinolizidin-1-ylmethyl) and in position 2 an aromatic moiety (phenyl, benzyl or benzotriazol-1/2-ylmethyl) were evaluated at the National Cancer Institute (NCI) for anti-proliferative activity against a panel of 60 human cancer cell lines. Four compounds (6, 7, 9 and 10) displayed a large spectrum of activity with [Formula: see text] 10 [Formula: see text] on 24-57 cell lines, while thirteen compounds exhibited sub-micromolar or even nanomolar activity against single cell lines, such as leukemia CCRF-CEM, HL-60 and MOLT-4, CNS cancer SF-268 and, particularly, renal cancer UO-31, sometimes with outstanding selectivity (compounds 5-7, 11, 13 and 18).

Synthesis and antiproliferative activity of pterostilbene and $$3^\prime $$ 3 ′ -methoxy pterostilbene Mannich base derivatives against Hela cells

“…Anticancer studies using several classes of polyaromatic antitumour agents indicate that the introduction of a nitrogen-containing side chain increases significantly the biological activity and potency of the parent compounds. For example, it has been shown that the presence of the nitrogen moiety in flavopiridol, a synthetic nitrogen-containing flavonoid with antitumor activity against various tumor cell lines, is critical for its antitumor effect [ 9 ]. The Mannich reaction is a commonly used way to introduce nitrogenous moieties, such as aminoalkyl group to phenols.…”

Functionalized Benzimidazole Scaffolds: Privileged Heterocycle for Drug Design in Therapeutic Medicine

“…Screening test of caspase‐dependent apoptosis showed 68 and 69 to be more potent than tirapazamine upon exposure to A549 cell. Other recently established anticancer benzimidazoles are 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , and 78 (Fig. ).…”

Exploring the effectiveness of novel benzimidazoles as CB2 ligands: synthesis, biological evaluation, molecular docking studies and ADMET prediction

“…During the last few years, our research group developed a large variety of benzimidazole derivatives with different pharmacological aims, in particular, exploring the analgesic, 18 antiviral [19][20][21] and anti-tumor 22 activities. Our benzimidazoles, studied in vivo as analgesic drugs, were designed on the basis of previous work of CIBA (now Novartis), that led to etonitazene, the most potent μ-opioid currently known.…”