A facile I₂-catalyzed synthesis of imidazo[1,2-a]pyridines via sp³ C–H functionalization of azaarenes and evaluation of anticancer activity

Abstract

A facile and efficient metal-free, one-pot, three component synthetic protocol has been developed for the synthesis of medicinally important substituted imidazo[1,2-a]pyridines via the iodine-catalysed oxidative amination of benzylic C-H bonds of azaarenes with 2-aminoazines and condensation with isocyanides. The presented methodology offers the advantages of wide substrate scope, moderate reaction conditions, environment friendliness, clean and simple protocol with high atom economy apart from higher yields. The synthesized compounds were screened for their anti-cancer activity in selected human cancer cell lines. Compounds 4a, 4b, 4c, 4i, 7a, 7b and 7m have significant IC values ranging from 4.88 ± 0.28 to 14.55 ± 0.74 μM.

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

“…Nitrogen‐containing heterocyclic compounds, such as imidazo[1,2‐ a ]pyridine (IP), an imidazopyridine derivative, are considered to be privileged structures due to their biological properties. [ 7 ] The IP cores are recognized as a “drug prejudice” scaffold [ 8 ] and have been widely exploited in medicinal chemistry due to their broad spectrum of pharmacological activities, making them a promising drug candidate for antitumor therapy in smaller toxic and equally effective doses. [ 9 ] Therefore, it is noteworthy to mention that the synthesis and functionalization of IP have received considerable attention from the scientific community .…”

New 3‐(1H‐benzo[d]imidazol‐2‐yl)quinolin‐2(1H)‐one‐based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis‐inducing agents

“…The cytotoxicity of synthesized compounds was evaluated using the MTT assay, which involves the conversion of yellow color MTT into purple formazan crystals by live cells. [ 38 ] Briefly, 3000–4000 cells were seeded in 100 μl of DMEM supplemented with 10% BS and 1% antibiotic–antimycotic mixture in each well of a 96‐well microtiter plate and incubated at 37°C and a 5% CO 2 environment in an incubator. The seeded cells were exposed to gradient concentrations (0.625–20 μM) of compounds along with the proper vehicle control for 48 h. After 48 h of incubation, the media were discarded and cells were washed twice with PBS.…”

Designing Novel Compounds for the Treatment and Management of RET-Positive Non-Small Cell Lung Cancer—Fragment Based Drug Design Strategy

“…These results are evident that the designed fragments able to replicate the binding pattern to that of pralsetinib. In addition, the carboxamide and azaarene functional groups that were identified in the hit molecules were reported recently to have anticancer activity [45,46]. The ADMET analysis of the compounds was performed using the QikProp module of Schrödinger and ProTox-II software to prevent the elimination of molecules during clinical trials.…”