Imidazole-pyridine hybrids as potent anti-cancer agents

Aruchamy, Baladhandapani; Drago, Carmelo; Russo, Venera; Pitari, Giovanni M.; Ramani, Prasanna; Aneesh, T P; Benny, Sonu; Vishnu, VR

doi:10.1016/j.ejps.2022.106323

Cited by 20 publications

(16 citation statements)

References 47 publications

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“…The imidazole–pyridine compound 5a was synthesized as per Scheme . , To prepare the desired compound, pyridine-3-carboxaldehyde, 4,4′-dimethylbenzil, and ammonium acetate were dissolved in ethanol. The resulting solution was then subjected to reflux for 12 h, utilizing a catalytic amount of iodine.…”

Section: Resultsmentioning

confidence: 99%

“…Imidazole and its derivatives are the most prevalent versatile units of heterocyclic chemistry, and they possess outstanding pharmaceutical activities to control cancer. − Clinical trials have evaluated the efficacy of various imidazole-containing drugs, including dacarbazine, temozolomide, etanidazole, azathioprine, zoledronic acid, pimonidazole, misonidazole, mercaptopurine, nilotinib, fadrozole, and tipifarnib, in the treatment of various types of cancer, with the current availability for clinical use. , Recently, our research efforts have focused on conducting comprehensive studies aimed at developing highly potent anticancer agents. There are numerous scientific studies available which employ innovative and novel synthetic methods to synthesize 2,4,5 tri- and 1,2,4,5 tetra-substituted imidazole heterocyclic compounds. − New hybrid molecules with potent biological activities are produced by the molecular hybridization approach, involving two or more biologically active pharmacophores. − The combination of these two significant moieties could lead to possible imidazole–pyridine hybrid molecules with enhanced biological activities. − The introduction of the hetero unit on position 2 of the imidazole scaffold exhibits potential anticancer activity . In addition, the phenyl rings present at positions 4 and 5 are increasingly crucial for the cytotoxicity of the imidazole moiety when compared to aliphatic substitution on these positions .…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, and Anti-Breast Cancer Potential of Imidazole–Pyridine Hybrid Molecules In Vitro and Ehrlich Ascites Carcinoma Growth Inhibitory Activity Assessment In Vivo

Aruchamy,

Kuruburu,

Bovilla

et al. 2023

ACS Omega

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Breast cancer remains a challenging medical issue and is a high priority for biomedical research despite significant advancements in cancer research and therapy. The current study aims to determine the anticancer activity of a group of imidazole−pyridine-based scaffolds against a variety of breast cancer cell lines differing in their receptor expression (estrogen receptor (ER), progesterone receptor (PR), and HER-2). A series of 10 molecules (coded 5a−5j) were synthesized through multicomponent and alkylation reactions. FTIR, MS, 1 H, and 13 C NMR spectral analyses confirmed the structures and purity of the synthesized molecules. Subsequently, these molecules were tested for their ability to inhibit the viability of cell lines representing carcinoma of the breast, viz., MDA-MB-468 (ER−, PR−, and HER−), BT-474 (ER+, PR+, and HER+), T-47D (ER+, PR+, and HER−), and MCF-7 (ER+, PR+, and HER−) in vitro. Among these 10 molecules, 5a, 5c, 5d, and 5e exhibited better potency, as evidenced by IC 50 < 50 μM at 24 h of treatment against BT-474 and MDA-MB-468 cell lines. However, except for 5d, the IC 50 value is much higher than 50 μM when tested against T47D and MCF-7 cell lines at 24h. Extended treatment for 48 h reduced the effect of these molecules, as an increase in IC 50 was observed. In mice, intraperitoneal administration of 5e retarded the Ehrlich ascites carcinoma (EAC) growth without causing any organ toxicity at the doses tested. In summary, we report the synthesis scheme and key structural requirements for a new series of imidazole−pyridine molecules for in vitro inhibition of the feasibility of breast cancer cells and in vivo inhibition of EAC tumors.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anti-Breast Cancer Potential of Imidazole–Pyridine Hybrid Molecules In Vitro and Ehrlich Ascites Carcinoma Growth Inhibitory Activity Assessment In Vivo

Aruchamy,

Kuruburu,

Bovilla

et al. 2023

ACS Omega

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“…Many pyrroles have been investigated for their anti-breastcancer properties, primarily in MCF-7 cells [146,148] (Figure 9). Pyrroles have been categorised in this area in two ways: Fused pyrroles and pyrroles with expanded functionality.…”

Section: Anti-breast Cancer Activitymentioning

confidence: 99%

“…Therefore, scientists are working to develop highly effective treatments for these non‐infectious disorders. Pyrrole is a potent heterocyclic moiety with anticancer, [146,147] antidiabetic, anti‐Alzheimer, and anti‐Parkinson effects. Several data from the literature are reviewed in‐depth in this section.…”

Section: Pyrroles For Non‐infectious Diseasesmentioning

confidence: 99%

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Ganesh,

Raj,

Aruchamy

et al. 2023

ChemMedChem

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An overview of pyrroles as distinct scaffolds with therapeutic potential and the significance of pyrrole derivatives for drug development are provided in this article. It lists instances of naturally occurring pyrrole‐containing compounds and describes the sources of pyrroles in nature, including plants and microbes. It also explains the many conventional and modern synthetic methods used to produce pyrroles. The key topics are the biological characteristics, pharmacological behavior, and functional alterations displayed by pyrrole derivatives. It also details how pyrroles are used to treat infectious diseases. It describes infectious disorders resistant to standard treatments and discusses the function of compounds containing pyrroles in combating infectious diseases. Furthermore, the review covers the uses of pyrrole derivatives in treating non‐infectious diseases and resistance mechanisms in non‐infectious illnesses like cancer, diabetes, and Alzheimer's and Parkinson's diseases. The important discoveries and probable avenues for pyrrole research are finally summarized, along with their significance for medicinal chemists and drug development. A reference from the last two decades is included in this review.

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“…Cancer is a prevalent and deadly aggressive disorder where the cells grow uncontrollably due to unregulated metabolism (Aruchamy et al, 2023). The currently available non-invasive cancer treatments are chemotherapy and radiotherapy, but sadly multidrug resistance (MDR) shuttled as a challenging task in cancer treatments, which leads to genomic alterations.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic and non‐heterocyclic arena of monocarboxylate transporter inhibitors to battle tumorigenesis

Manisha,

Ratheesh,

Benny

et al. 2023

Chem Biol Drug Des

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Monocarboxylate transporters (MCTs) have gained significant attention in cancer research due to their critical role in tumour metabolism. MCTs are legends for transporting lactate molecules in cancer cells, an oncometabolite and waste product of glycolysis, acting as an indispensable factor of tumour proliferation. Targeting MCTs with inhibitors has emerged as a promising strategy to combat tumorigenesis. This article summarizes the most recent research on MCT inhibitors in preventing carcinogenesis, covering both heterocyclic and non‐heterocyclic compounds. Heterocyclic and non‐heterocyclic compounds such as pteridine, pyrazole, indole, flavonoids, coumarin derivatives and cyanoacetic acid derivatives have been reported as potent MCT inhibitors. We examine the molecular underpinnings of MCTs in cancer metabolism, the design and synthesis of heterocyclic and non‐heterocyclic MCT inhibitors, their impact on tumour cells and the microenvironment and their potential as therapeutic agents. Moreover, we explore the challenges associated with MCT inhibitor development and propose future directions for advancing this field. This write‐up aims to provide researchers, scientists and clinicians with a comprehensive understanding of the heterocyclic and non‐heterocyclic MCT inhibitors and their potential in combating tumorigenesis.

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Imidazole-pyridine hybrids as potent anti-cancer agents

Cited by 20 publications

References 47 publications

Design, Synthesis, and Anti-Breast Cancer Potential of Imidazole–Pyridine Hybrid Molecules In Vitro and Ehrlich Ascites Carcinoma Growth Inhibitory Activity Assessment In Vivo

Design, Synthesis, and Anti-Breast Cancer Potential of Imidazole–Pyridine Hybrid Molecules In Vitro and Ehrlich Ascites Carcinoma Growth Inhibitory Activity Assessment In Vivo

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Heterocyclic and non‐heterocyclic arena of monocarboxylate transporter inhibitors to battle tumorigenesis

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