Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies

Bakherad, Zohreh; Safavi, Maliheh; Sepehri, Saghi; Fassihi, Afshin; Sadeghi‐Aliabadi, Hojjat; Bakherad, Mohammad; Rastegar, Hossein; Larijani, Bagher; Saghaie, Lotfollah; Mahdavi, Mohammad

doi:10.1007/s11164-019-03915-z

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…Among the tested cell lines, compound 95 showed excellent activity against A-549 cell lines with the IC 50 value 25.67 µM. Etoposide was used as a standard with IC 50 values 1.76, 5.93, 7.1, and 4.96 µM, respectively [ 219 ].…”

Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Kumar

Singh

et al. 2023

Pharmaceuticals

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Cancer is one of the major healthcare challenges across the globe. Several anticancer drugs are available on the market but they either lack specificity or have poor safety, severe side effects, and suffer from resistance. So, there is a dire need to develop safer and target-specific anticancer drugs. More than 85% of all physiologically active pharmaceuticals are heterocycles or contain at least one heteroatom. Nitrogen heterocycles constituting the most common heterocyclic framework. In this study, we have compiled the FDA approved heterocyclic drugs with nitrogen atoms and their pharmacological properties. Moreover, we have reported nitrogen containing heterocycles, including pyrimidine, quinolone, carbazole, pyridine, imidazole, benzimidazole, triazole, β-lactam, indole, pyrazole, quinazoline, quinoxaline, isatin, pyrrolo-benzodiazepines, and pyrido[2,3-d]pyrimidines, which are used in the treatment of different types of cancer, concurrently covering the biochemical mechanisms of action and cellular targets.

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Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Kumar

Singh

et al. 2023

Pharmaceuticals

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“…[11] Additionally, Bakherad & group members reported the synthesis and biological evaluation of a series of imidazopyridine derivatives of indole under reflux conditions using NH 4 Cl as a catalyst and toluene as a solvent (Scheme 1d). [12] At present, the available methods for the production of indole-based imidazopyridine derivatives are challenging. As a result, there is a substantial need for catalysts that are more cost-effective, easily affordable, and environmentfriendly to synthesize indole-based imidazo[1,2-a]pyridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…Further, Kamal and coworkers also performed the synthesis of novel bisindole‐imidazopyridine hybrids and evaluated their potential as anticancers (Scheme 1c) [11] . Additionally, Bakherad & group members reported the synthesis and biological evaluation of a series of imidazopyridine derivatives of indole under reflux conditions using NH 4 Cl as a catalyst and toluene as a solvent (Scheme 1d) [12] . At present, the available methods for the production of indole‐based imidazopyridine derivatives are challenging.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Indole‐Based Imidazopyridine using α‐Amylase

Kamboj,

Tyagi

2024

ChemBioChem

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The imidazo[1,2‐a]pyridine scaffold has gained significant attention due to its presence as a lead structure in several commercially available pharmaceuticals like zolimidine, zolpidem, olprinone, soraprazan, etc. Further, indole‐based imidazo[1,2‐a]pyridine derivatives have been found interesting due to their anticancer and antibacterial activities. However, limited methods have been reported for the synthesis of indole‐based imidazo[1,2‐a]pyridines. In this study, we have successfully developed a biocatalytic process for synthesizing indole‐based imidazo[1,2‐a]pyridine derivatives using the α‐amylase enzyme catalyzed Groebke‐Blackburn‐Bienayme (GBB) multicomponent reaction of 2‐aminopyridine, indole‐3‐carboxaldehyde, and isocyanide. The generality and robustness of this protocol were shown by synthesizing differently substituted indole‐based imidazo[1,2‐a]pyridines in good isolated yields. Furthermore, to make α‐amylase a reusable catalyst for GBB multicomponent reaction, it was immobilized onto magnetic metal‐organic framework (MOF) materials [Fe3O4@MIL‐100(Fe)] and found reusable up to four consecutive catalytic cycles without the significant loss in catalytic activity.

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Antitumor Activity of New Pd(II) Complexes with Ligands Derived from O‐Vanillin Acting as Topoisomerase I and II Inhibitors

Franco,

Guedes,

Batista

et al. 2024

ChemistrySelect

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This study investigates topoisomerase I and II enzyme inhibition by novel Pd(II) complexes. TSC represents the chelating ligand thiosemicarbazone, which is modified at its 4(N)‐nitrogen terminal position with substituents such as C2H5, CH3, and H. PR3 represents the triphenylphosphine ligand, with positional variations including para substituents H, F, OCH3, and CH3. The aim is to establish a correlation between these molecular variations and cytotoxicity. In particular, the compounds show promising cytotoxicity against MDA‐MB‐231 and A549 tumor cell lines, especially those with H substitution at the terminal position 4(N) of TSC and H and F in the triphenylphosphine. The results suggest that a smaller molecular volume of ligand substituents may enhance the cytotoxic effects. The inhibitory potential of the complexes against DNA topoisomerase enzymes was investigated. The IC₅₀ values of the most promising complexes strongly inhibit TOPOIIα and TOPOIβ, suggesting these enzymes as primary targets. These complexes exhibited significantly lower IC₅₀ values (4.32–4.88 μM) compared to cisplatin (10.2 μM) against MDA‐MB‐231 cells, indicating a distinct mode of action. However, it is noteworthy that the complexes did not inhibit the action of DNA topoisomerase IIβ, suggesting selectivity against specific isoforms of DNA topoisomerase II that act as catalytic inhibitors.

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Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies

Cited by 6 publications

References 27 publications

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Enzymatic Synthesis of Indole‐Based Imidazopyridine using α‐Amylase

Antitumor Activity of New Pd(II) Complexes with Ligands Derived from O‐Vanillin Acting as Topoisomerase I and II Inhibitors

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