Synthesis, Characterization, and Anticancer Activity of Novel Imidazo[1,2-a]pyridine Linked 1,2,3-Triazole Derivatives

Endoori, Srinivas; Anna, Venkateswara Rao; Gulipalli, Kali Charan; Bodige, Srinu; Pommidi, Anil Kumar; Surapureddi, Sri Ramakrishna; Seelam, Nareshvarma

doi:10.1134/s1070363222090195

Cited by 2 publications

(4 citation statements)

References 13 publications

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“…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.…”

Section: 23-triazole-azole Hybridsmentioning

confidence: 99%

“…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 ]…”

Section: Indole‐pyridine/quinoline Hybridsmentioning

confidence: 99%

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

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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Section: 23-triazole-azole Hybridsmentioning

confidence: 99%

Section: Indole‐pyridine/quinoline Hybridsmentioning

confidence: 99%

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

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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“…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.…”

Section: Introductionmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Rejinthala,

Endoori,

Thumma

et al. 2024

ChemistrySelect

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Design and synthesis of a series of novel hybrid molecules that combine Imidazo[4,5‐c] pyridines with piperdines are presented in this paper. Total 17 derivatives were meticulously synthesized and characterized using 1H NMR, 13C NMR, MS and elemental analysis techniques. The in vitroanticancer activities are estimated by verifying their effectiveness against the MCF‐7 human breast adenocarcinoma and A549 lung cancer cell line, with cisplatin and doxorubicin serving as reference drugs. Several of these compounds demonstrated significant potential, displaying IC50 values within the range of 12.26–84.5 μM for A549, and 13.37–69.82 μM for MCF‐7. Notably, compound 11 bis found to be more potent than the standard drug cisplatin with an IC50 of 12.26±0.8 μM against A549 cells, while compound 11 d exhibited highest inhibition with an IC50 of 13.37±0.4 μM against MCF‐7 cells. Although its effectiveness was moderately lower when compared to doxorubicin, it still retained substantial anticancer activity. Molecular docking studies were performed to decouple the binding affinity and ligand interactions of the compounds with the estrogen receptor alpha (ERα) (PDB ID: 3ERT). The pharmacokinetic evaluation revealed favourable drug‐likeness properties for all the molecules, suggesting their potential as therapeutic agents.

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Synthesis, Characterization, and Anticancer Activity of Novel Imidazo[1,2-a]pyridine Linked 1,2,3-Triazole Derivatives

Cited by 2 publications

References 13 publications

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

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

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

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