Design, synthesis, biological assessment and molecular docking studies of new 2-aminoimidazole-quinoxaline hybrids as potential anticancer agents

Ghanbarimasir, Zahra; Bekhradnia, Ahmadreza; Morteza‐Semnani, Katayoun; Rafiei, Alireza; Razzaghi‐Asl, Nima; Kardan, Mostafa

doi:10.1016/j.saa.2017.12.063

Cited by 28 publications

(15 citation statements)

References 54 publications

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“…Furthermore, quinoxaline 5 having an amide group (Figure 2) has been also reported by Ramurthy et al as a potent Rapidly Accelerated Fibrosarcoma (Raf) kinase inhibitor [14]. Finally, quinoxalines were recently reported to exhibit inhibition against MCF-7 (83.3%) and HCT116 (70%) cell lines [15].…”

Section: Introductionmentioning

confidence: 82%

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

et al. 2019

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The quinoxaline scaffold is a promising platform for the discovery of active chemotherapeutic agents. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines (HCT116 human colon carcinoma, HepG2, liver hepatocellular carcinoma and MCF-7, human breast adenocarcinoma cell line), in addition to VEGFR-2 enzyme inhibition activity. Compounds VIId, VIIIa, VIIIc, VIIIe and XVa exhibited promising activity against the tested cell lines and weak activity against VEGFR-2. Compound VIIIc induced a significant disruption in the cell cycle profile and cell cycle arrest at the G2/M phase boundary. In further assays, the cytotoxic effect of the highly active compounds was determined using a normal Caucasian fibroblast-like fetal lung cell line (WI-38). Compound VIIIc could be considered as a lead compound that merits further optimization and development as an anti-cancer and an apoptotic inducing candidate against the HCT116 cell line.

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Section: Introductionmentioning

confidence: 82%

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

et al. 2019

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“…As SAR analysis, the electron‐donating groups like methyl, ethoxy, 4,6‐dimethoxy, 3,4,5‐trimethoxy at both rings enhanced the activity but the electron‐withdrawing groups like fluorine, chlorine, bromine, nitro group diminished the activity (Figure 52). [124] …”

Section: Imidazole Hybridizes With Other Anticancer Pharmacophoresmentioning

confidence: 99%

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

Teli¹,

Chawla²

2021

ChemistrySelect

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Cancer is the world‘s biggest global health concern. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Approximately 24.6 million people are suffering from cancer across the world as per the world health organization (WHO). In the year 2020, approximately 10 million deaths were reported due to cancer which has emerged as the second leading cause of mortality across the globe. Anticancer medicines have played a pivotal role in the medication of different types of cancers; however, they are associated with several side effects and relevance of drug resistance which evoke an immediate need for designing of new anticancer agents with multitargeted effect. Imidazole is a heterocyclic compound privileged with considerable anticancer activities and some imidazole derivatives have already got approval to treat cancer. Many hybrid molecules are available that play an important role in the treatment of cancer like chalcone, pyrazole, purine, triazine etc., and their pharmacophore provide the anticancer drug with low drug resistance and high efficacy, with low chances of toxicity and side effects. This review provides various approaches for the drug development of new safe and efficient antitumor agents imidazole hybrids with other heterocyclic moieties. An attempt has been made to advancement of the anticancer potential of the derivatives and hybrids of imidazole having intact or condensed imidazole moiety in the last decade along with the structure‐activity relationship studies, and mechanism of action.

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“…55 C). [5,26] Typical experimental procedure for the synthesis of 2-chloroquinoxaline (III) 2-Chloroquinoxaline (III) was prepared according to a previously reported method (Scheme 1). Freshly distilled phosphorus oxychloride POCl 3 (10 ml) was added slowly dropwise to quinoxalin-2-ol (II) (10.26 mmol: 1.5 g) at 0 C, and a few drops of dimethylformamide (DMF) were added to the mixture and refluxed for 12 h. Excess POCl 3 was distilled under reduced pressure, and the residue was cooled to room temperature and added to crushed ice.…”

Section: Chemistrymentioning

confidence: 99%

“…[1,2] Among these, quinoxaline (benzopyrazine) derivatives, especially 2-amino quinoxalines as well as benzimidazole moiety, play a vital role in the development of biological compounds with valuable activities, including antiviral, antibacterial, antimicrobial, antifungal, antimalarial, antidepressant, antidiabetic and kinase (c-Met) inhibitory, and anticancer effects. [3][4][5] In addition, quinoxaline as a bioisostere of different heterocyclic systems such as benzimidazole, pteridine, quinazoline, quinoline, benzothiophene, pyridine, and pyrazine has become a significant portion of various bioactive small molecules in the pharmaceutical field. [6] Because of the extensive activity of these scaffolds, the synthesis of the heterocyclic compounds as biologically active agents have always been at the center of attention.…”

Section: Introductionmentioning

confidence: 99%

“…[ 1,2 ] Among these, quinoxaline (benzopyrazine) derivatives, especially 2‐amino quinoxalines as well as benzimidazole moiety, play a vital role in the development of biological compounds with valuable activities, including antiviral, antibacterial, antimicrobial, antifungal, antimalarial, antidepressant, antidiabetic and kinase (c‐Met) inhibitory, and anticancer effects. [ 3–5 ]…”

Section: Introductionmentioning

confidence: 99%

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One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe₃O₄ MNPs as highly effective nanocatalyst

Esam

Akhavan

Bekhradnia

2020

Applied Organom Chemis

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The immobilization of sulfonic acid on the surface of Fe 3 O 4 magnetic nanoparticles (MNPs) as a novel acid nanocatalyst has been successfully reported. The morphological features, thermal stability, magnetic properties, and other physicochemical properties of the prepared superparamagnetic core-shell (Fe 3 O 4 @PFBA-Metformin@SO 3 H) were thoroughly characterized using Fourier transform infrared (FTIR), X-ray diffraction (XRD), energydispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermogravimetric analysis-differential thermal analysis (TGA-DTA), atomic force microscopy (AFM), dynamic light scattering (DLS), Brunauer-Emmett-Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives via a one-pot multiple-component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe 3 O 4 @PFBA-metformin@SO 3 H as an organic-inorganic hybrid nanocatalyst in condensation and multicomponent Mannich-type reactions. The easy separation, simple workup, excellent stability, and reusability of the nanocatalyst and quantitative yields of products and short reaction time are some outstanding advantages of this protocol.

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Design, synthesis, biological assessment and molecular docking studies of new 2-aminoimidazole-quinoxaline hybrids as potential anticancer agents

Cited by 28 publications

References 54 publications

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe₃O₄ MNPs as highly effective nanocatalyst

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Design, synthesis, biological assessment and molecular docking studies of new 2-aminoimidazole-quinoxaline hybrids as potential anticancer agents

Cited by 28 publications

References 54 publications

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst

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One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe₃O₄ MNPs as highly effective nanocatalyst