Anticancer properties of N-alkyl-2, 4-diphenylimidazo [1, 2-a] quinoxalin-1-amine derivatives; kinase inhibitors

Rezaei, Zahra; Didehvar, Mir Mahdi; Mahdavi, Mohammad; Azizian, Homa; Hamedifar, Haleh; Mohammed, Eman H. M.; Ostad, Sayednaser; Amini, Mohsen

doi:10.1016/j.bioorg.2019.103055

Cited by 11 publications

(9 citation statements)

References 37 publications

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“…As it is shown in Figure 7, the obtained results from redocking and the crystallographic structure are in agreement in terms of the ligand interactions, position, and orientation in the active pocket of the enzyme. The root mean square distance (RMSD) of re‐docked and co‐crystallized ligand over 4XCT was less than 2.0 Å that confirmed the accuracy of docking protocol 65 …”

Section: Resultsmentioning

confidence: 70%

“…The root mean square distance (RMSD) of re-docked and cocrystallized ligand over 4XCT was less than 2.0 Å that confirmed the accuracy of docking protocol. 65 Binding position and interaction of the active compounds. Molecular docking is a popular computational method that is used in the prediction of binding modes of a potential bioactive compound with its biomolecular target.…”

Section: Biological Evaluationmentioning

confidence: 99%

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Synthesis of Biuret Derivatives as Potential HIV‐1 Protease Inhibitors Using (LDHs‐g‐HMDI‐Citric Acid), as a Green Recyclable Catalyst

Salehabadi

Adibpour

Alipour

et al. 2020

Bulletin Korean Chem Soc

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In this study, a novel catalyst based on layered double hydroxides (LDHs) attached by hexamethylene-1,6-diisocyanate (HMDI) and citric acid (LDHs-g-HMDI-Citric acid) is reported and used to increase the yield of biurets synthesis. Biuret derivatives 5a-n were prepared by reaction of several phenyl allophanates (3a-d), which prepared from the reaction of phenyl chloroformate and urea derivatives (2ad), with variously substituted amines (4a-g) in the presence of LDHs-g-HMDI-Citric acid as a reusable heterogeneous catalyst at reflux condition for 60-180 min. These biurets (5a-n) were evaluated for human immunodeficiency virus type-1 (HIV-1) protease inhibitory activity by HIV-1 p24 antigen ELISA kit and six of them (5n, 5i, 5j, 5 m, 5f, and 5a) showed moderate activity on HIV-1 virus with IC 50 values ranging from 55 to 100 μM compared with the azidothymidine as the reference drug (IC 50 = 0.11 μM). Results of the in vitro test and docking study were in good correlation.

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Section: Resultsmentioning

confidence: 70%

Section: Biological Evaluationmentioning

confidence: 99%

Synthesis of Biuret Derivatives as Potential HIV‐1 Protease Inhibitors Using (LDHs‐g‐HMDI‐Citric Acid), as a Green Recyclable Catalyst

Salehabadi

Adibpour

Alipour

et al. 2020

Bulletin Korean Chem Soc

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“…Rezaei et al prepared a series of diphenylimidazo-quinoxalinamine derivatives as anticancer candidates [ 65 ]. Compounds 52, 53 , and 54 showed the greatest potencies against the K562 cell line (IC 50 values of 9.77, 12.02, and 15.84 µM, respectively).…”

Section: Imidazoles As Kinase Inhibitorsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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“…[40] In 2009, Krasavin and group developed two isocyanide-based (11 and 12) multicomponent reactions for the synthesis of imidazo[1,2a]quinoxalines [41], while Rezaei and group reported multicomponent synthesis from 2-aminoquiniline (13), benzaldehydes (14) and cyanides (15) in the presence of trace amounts of ammonium chloride. [42]…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

et al. 2022

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Cancer, the uncontrolled growth of cells, is not a single but a multifaceted disorder with malignant behavior, metastasis, and invasion, medically known as malignant neoplasm. The number of cases and morbidity due to cancer is rising alarmingly worldwide, causing around 21 % annually. Imidazoquinoxaline is a privileged scaffold with a wide range of pharmacological activities that is well explored for its anticancer potential. As a synthon, imidazoquinoxaline presents a large number of possibilities for structural modifications, which have attained the attention of many researchers for the development of new anticancer molecules with diverse improved target specificity and efficiency. Development of imiquimod followed by EAPB203 and EAPB503 derivatives further enhanced the popularity of this structural pharmacophore. In this report, we have focused on the anticancer potential of newly reported imidazoquinoxaline derivatives, along with their SAR studies and therapeutic potential. We have also enlisted the synthetic schemes reported for the synthesis of imidazoquinoxaline derivatives. The lead structural features described in this review will assist the researchers in designing and developing the novel imidazoquinoxaline pharmacophore containing anticancer compounds possessing the potential to interfere with various factors or mediators which are responsible for the progression of cancer. This report will also help in identifying the potent compounds which can be further evaluated in clinical trials for the development of new anticancer drugs with minimal to no side effects.

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Anticancer properties of N-alkyl-2, 4-diphenylimidazo [1, 2-a] quinoxalin-1-amine derivatives; kinase inhibitors

Cited by 11 publications

References 37 publications

Synthesis of Biuret Derivatives as Potential HIV‐1 Protease Inhibitors Using (LDHs‐g‐HMDI‐Citric Acid), as a Green Recyclable Catalyst

Synthesis of Biuret Derivatives as Potential HIV‐1 Protease Inhibitors Using (LDHs‐g‐HMDI‐Citric Acid), as a Green Recyclable Catalyst

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Imidazoquinoxaline as a Privileged Fused Pharmacophore in Anticancer Drug Development: A Review of Synthetic Strategies and Medicinal Aspects

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