Synthesis of 3H-imidazo[4,5-b] pyridine with evaluation of their anticancer and antimicrobial activity

Abstract

Microwave assisted and conventional synthetic methods of new 6-bromo-2-(substituted)-3H-imidazo [4,5-b]pyridine and its derivatives are described, which were obtained in reduced reaction times, higher yields, cleaner reactions than previously described methods. All the synthesized compounds were characterized, and screened for their anticancer and antimicrobial activity. Among synthesized compounds 3b and 3k shows prominent antibacterial activity and compound 3f shows both antibacterial and antifungal activity. Compounds 3h and 3j shows prominent anticancer activity against the both breast cancer cell lines, MCF-7 and BT-474. These results suggest that the imidazo [4,5-b]pyridine moiety may serve as a new promising template for synthesis of anticancer and antimicrobial agents and further study is required for evaluation of their mechanism of action.

Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States

“…All of the chemicals used for synthesis were procured from Sigma-Aldrich. The compounds were synthesized using the procedure followed for similar kinds of molecules. , A brief synthetic procedure and the characterization data are provided below.…”

“…DHP was synthesized by refluxing an equimolar amount of 2,3-diaminopyridine and 4- N,N -diethylaminosalicylaldehyde in N,N -dimethylformamide (DMF) at 120 °C (Scheme S1), purified by column chromatography, and confirmed by NMR (Figures S1 and S2) and HRMS. 1 H NMR (600 MHz, DMSO- d 6 , δ ppm): 12.87 (s, 1H), 8.24 (dd, 1H), 7.94 (d, 1H), 7.86 (t, 1H), 7.20 (m, 1H), 6.38 (m, 1H), 6.20 (d, 1H), 3.39 (m, 4H), 1.12 (t, 6H).…”

“…Synthesis of 2-(4′-Diethylamino-2′-hydroxyphenyl)-1H-imidazo [4,5-b]pyridine (DHP). DHP was synthesized by refluxing an equimolar amount of 2,3diaminopyridine and 4-N,N-diethylaminosalicylaldehyde in N,N-dimethylformamide (DMF) at 120 °C (Scheme S1), 49 purified by column chromatography, and confirmed by NMR (Figures S1 and S2) and HRMS. 1 2.2.…”

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs

“…The best yields were obtained under the optimized conditions rather than using solvents such as methanol, ethanol, toluene, DMF or acetic acid and the yield% depends on the type of the catalyst. 91 …”

Synthesis and evaluation of pyridinium‐hydrazone derivatives as potential antitumoral agents

“…[30] As various studies have revealed that some of the antimicrobial compounds having toxicity on bacteria display cytotoxic activity against cancer cells, [27][28][29] we evaluated the effect of the distance between the pyridinium nitrogen and the phenyl ring on the cytotoxic activity. [30] As various studies have revealed that some of the antimicrobial compounds having toxicity on bacteria display cytotoxic activity against cancer cells, [27][28][29] we evaluated the effect of the distance between the pyridinium nitrogen and the phenyl ring on the cytotoxic activity.…”