Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

Caymaz, Bahar; Yıldız, Ufuk; Akkoç, Senem; Gerçek, Zuhal; Şengül, Abdurrahman; Çoban, Burak

doi:10.1002/slct.202001580

Cited by 8 publications

(5 citation statements)

References 83 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In another study, Atmaca et al ( Atmaca et al, 2020 ) disclosed significant cytotoxicity of compound 292 against breast cancer (MCF-7), prostate cancer (DU-145), and lung cancer (H69AR) with IC50 values of 17.8 ± 0.24, 10.2 ± 1.4 and 49.9 ± 0.22 μg/ml, respectively, compared to 5-Fluorouracil. Compounds 293–294 showed stronger anticancer property against HepG2 (IC 50 : 26.62 and 20.29, respectively) and DLD-1 cells (IC 50 : 21.29 and 19.23 µM, respectively) than cisplatin (IC 50 : 30.38 and 60.79 µM) ( Caymaz et al, 2020 ). Particularly, compound 295–296 demonstrated potent anti-breast cancer effect by obstructing MCF-7 cell growth compared to standard cisplatin (IC 50 : 0.016 ± 0.001 and 0.018 ± 0.001 vs. 0.020 ± 0.009 µM).…”

Section: Biological Activitiesmentioning

confidence: 99%

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

et al. 2021

View full text Add to dashboard Cite

Nowadays, nitrogenous heterocyclic molecules have attracted a great deal of interest among medicinal chemists. Among these potential heterocyclic drugs, benzimidazole scaffolds are considerably prevalent. Due to their isostructural pharmacophore of naturally occurring active biomolecules, benzimidazole derivatives have significant importance as chemotherapeutic agents in diverse clinical conditions. Researchers have synthesized plenty of benzimidazole derivatives in the last decades, amidst a large share of these compounds exerted excellent bioactivity against many ailments with outstanding bioavailability, safety, and stability profiles. In this comprehensive review, we have summarized the bioactivity of the benzimidazole derivatives reported in recent literature (2012–2021) with their available structure-activity relationship. Compounds bearing benzimidazole nucleus possess broad-spectrum pharmacological properties ranging from common antibacterial effects to the world’s most virulent diseases. Several promising therapeutic candidates are undergoing human trials, and some of these are going to be approved for clinical use. However, notable challenges, such as drug resistance, costly and tedious synthetic methods, little structural information of receptors, lack of advanced software, and so on, are still viable to be overcome for further research.

show abstract

Section: Biological Activitiesmentioning

confidence: 99%

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

et al. 2021

View full text Add to dashboard Cite

show abstract

“…As described in the experimental section (supplementary material), the MTT test was performed against four cancer cell lines specifically MCF-7, Caco-2, MDA231, T47D, [17,18] and one normal cell line, namely skin Fibroblasts (PCS201012). [19,20] which was selected as a reference of normal cells to evaluate the safety of our products as reported in table 1.…”

Section: Mtt Assaymentioning

confidence: 99%

Synthesis and Antiproliferative Activity of 4β‐O‐Substituted, 4β‐N‐Substituted Deoxypodophyllotoxin Derivatives, and 4β‐OH‐ 4’‐O‐Substituted Podophyllotoxin

et al. 2020

View full text Add to dashboard Cite

Podophyllotoxin (PPT) and its derivatives possess various biological activities and particularly against numerous cancers. The high toxicity and side effects of this therapeutic class are behind the restricted deployment in clinical applications. Here, we have identified and reported the synthesis of 4β‐O‐substituted 4’‐O‐demethylpodphyllotoxin derivatives, 4β‐N‐substituted 4’‐O‐demethyl‐4‐ deoxypodophyllotoxin derivatives and 4β‐OH‐ 4’‐O‐substituted podophyllotoxin derivative (series a, e and p) respectively. These derivatives are either esters or amides of various heterocyclic moieties which include imidazole, thiazole, pyrazole, and indole. Their synthesis was carried out in one step reaction and obtained in good yield. We tested all prepared compounds against T47D, MDA231, Caco‐2, and MCF‐7 cancer cell lines. They have been shown to possess significant biological activity, where series “a” has been demonstrated to be the most potent one. Compound 3 a exhibits potential activity in the micromolar range scoring 11 μM against Caco‐2 and 18 μM against MDA231. Consequently, all synthesized compounds have been evaluated for their safety profile and tested against PCS201012 which are normal skin fibroblast cell lines showing noticeable safety. The biological results demonstrate that the presence of an aromatic heterocycle ring in position 4 and 4’ lead to derivatives less toxic compared to podophyllotoxin and epipodophyllotoxin. Also, they are less potent. However, the results obtained will have, in future work, an important impact on the development of more potent and less toxic leads.

show abstract

“…[17] Benzimidazole derivatives have been reported for anticancer efficacy, [18] potential antitumor activity, [19] antiinflammatory activity, [20] anticonvulsant activity. [21] The phthalimide derivatives have been reported for anticancer activity, [22] anti-inflammatory, [23] antiproliferative, [24] in vitro anti antibacterial activity. [25]…”

Section: Introductionmentioning

confidence: 99%

An Experimental and Theoretical Study of the Conformational Stability of Triazinone Fleximers: Quantitative Analysis for Intermolecular Interactions

Kumar

Singh²,

Kumar³

et al. 2023

ChemistrySelect

View full text Add to dashboard Cite

Synthesis and characterization of triazinone based propylene linked phthalimide and benzimidazole have been carried out for conformational analysis and the study of their quantitative intermolecular interactions. The conformational analyses have been calculated by X-ray crystallography in the solid state and theoretical calculations in the gaseous state. From the crystal structure and theoretical calculations we have found that all compounds are stable in the folded conformation. These stable conformations are stabilized by different intra and intermolecular interactions, such as CÀ H⋯O, CÀ H⋯N, CÀ H⋯π and π⋯π. Quantitative intermolecular interactions and interactions energy calculations of both compounds have been carried out by Hirshfeld surface analysis.

show abstract

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

Cited by 8 publications

References 83 publications

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives

Synthesis and Antiproliferative Activity of 4β‐O‐Substituted, 4β‐N‐Substituted Deoxypodophyllotoxin Derivatives, and 4β‐OH‐ 4’‐O‐Substituted Podophyllotoxin

An Experimental and Theoretical Study of the Conformational Stability of Triazinone Fleximers: Quantitative Analysis for Intermolecular Interactions

Contact Info

Product

Resources

About