Design, synthesis, anticancer activity, and in silico studies of novel imidazo[1,2‐a]pyridine based 1H‐1,2,3‐triazole derivatives

Abstract

A novel series of imidazo[1,2-a]pyridine based 1H-1,2,3-triazole derivatives were designed, synthesized, and evaluated for their anticancer activity against two different human cancer cell lines. Most of the synthesized compounds displayed anticancer activity with IC 50 values from 2.35 to 120.46 μM. Furthermore, compounds 9b, 9c, 9d, 9f, and 9j showed potent inhibitory activity against cancer cell lines, with IC 50 values close to that of standard drug. It is important to note that compound 9d was more potent than the standard drug cisplatin with IC 50 values of 10.89 and 2.35 μM against Hela cell line and MCF-7 cell line, respectively.

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

“…SAR demonstrated that the terminal tetrahydrofuran fragment was essential for the high activity. [105,106] 1,2,3-Triazole-purine-bispyridine hybrid 81 (GI 50 : 8.303 and 6.158 µM, MTT assay) showed moderate antiproliferative activity against SK-Br3 and HCC1954 breast cancer cell lines, but the antiproliferative activity was far inferior to that of dinaciclib (GI 50 : 0.012 and 0.012 µM). [107] 1,2,3-Triazole-quinoline hybrids 82 (IC 50 : 6.45-53.91 µM, MTT assay) showed considerable antiproliferative activity against MCF-7 breast cancer cells, and the SAR indicated that chloro on the phenyl ring at N-1 position of 1,2,3-triazole motif was beneficial for the activity.…”

“…1,2,3‐Triazole‐imidazo[1,2‐ a ]pyridine hybrids 80a,b (IC 50 : 2.35 and 2.55 µM, respectively, MTT assay) were more active than cisplatin (IC 50 : 4.05 µM) against MCF‐7 breast cancer cells, and the SAR demonstrated that the terminal tetrahydrofuran fragment was essential for the high activity. [ 105,106 ] 1,2,3‐Triazole‐purine‐bis‐pyridine hybrid 81 (GI 50 : 8.303 and 6.158 µM, MTT assay) showed moderate antiproliferative activity against SK‐Br3 and HCC1954 breast cancer cell lines, but the antiproliferative activity was far inferior to that of dinaciclib (GI 50 : 0.012 and 0.012 µM). [ 107 ]…”

New Imidazo[4,5‐c]pyridine‐piperidine Hybrids as Potential Anti‐cancer Agents and In‐Silico Studies

“…This class includes various isomeric forms, such as imidazo [4,5-b]pyridines, imidazo [4,5-c]pyridines, imidazo [1,5-a]pyridines, and imidazo [1,2-a]pyridines. [9,10] These compounds possess unique structural characteristics and have attracted significant attention in medicinal chemistry research. Notably, the imidazo [4,5-c] pyridines exhibit a bio-isosteric resemblance to the purine nucleus, sharing similar structural and electronic properties.…”

“…Among these compounds, imidazopyridines, featuring an imidazole ring fused with a pyridine moiety, stand out as a distinct class. This class includes various isomeric forms, such as imidazo[4,5‐b]pyridines, imidazo[4,5‐c]pyridines, imidazo[1,5‐a]pyridines, and imidazo[1,2‐a]pyridines [9,10] . These compounds possess unique structural characteristics and have attracted significant attention in medicinal chemistry research.…”

Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies

“…To that end, a Cu(I)-catalyzed azide alkyne Huisgen 1,3-cycloaddition was used [ 50 , 51 , 52 , 53 ]. Moreover, we hope that the introduction of triazole linkers, known by their broad and abundant biological properties (antiviral [ 54 ], antioxidant [ 55 , 56 ], antimicrobial [ 57 ], anticancer [ 58 , 59 ], antimalarial [ 60 , 61 ]...) could contribute to the improvement of the overall biological activity of the hybrid molecules [ 62 , 63 , 64 , 65 , 66 ]. The antibacterial activity of OA-1 and the target compounds werescreened, followed by in silico molecular docking studies for the most potent derivatives, in order to obtaina better understanding about the interactions and binding mode in the active sites of the target protein.…”