Developing lipophilic aromatic halogenated fused systems with specific ring orientations, leading to potent anticancer analogs and targeting the c-Src Kinase enzyme

Ahmed, Hany E. A.; El-Nassag, Mohammed A. A.; Hassan, Ahmed H.E.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; El‐Gilil, Shimaa M. Abd; Khattab, Essam Shawky A. E. H.; Fouda, Ahmed M.; El‐Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H.

doi:10.1016/j.molstruc.2019.03.012

Cited by 34 publications

(16 citation statements)

References 31 publications

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“…A novel series of substituted-6-methoxy-4H-benzo [h]chromenes was reported by Ahmed et al ( 2019 ) and evaluated their anticancer potency. The surprising result was shown with the MCF-7 cell line, compounds 17 , 18 , 19 , 20 , 21 , and 22 showed the significant inhibition of MCF-7 (IC 50 1.2–5.5 μg/mL).…”

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

“…Among them, compound 21 exhibited highly significant activity (IC 50 0.1432 μM) against c-Src kinase. Overall, the studies suggested that the substitution of lipophilic electron-withdrawing such as -Br or an electron-donating likely -OCH 3 in the naphthalene motif is highly suitable than the unsubstituted naphthalene to the inhibition of c-Src kinase (Ahmed et al, 2019 ).…”

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

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2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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2H/4H-chromene (2H/4H-ch) is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. Researchers discovered several routes for the synthesis of a variety of 2H/4H-ch analogs that exhibited unusual activities by multiple mechanisms. The direct assessment of activities with the parent 2H/4H-ch derivative enables an orderly analysis of the structure-activity relationship (SAR) among the series. Additionally, 2H/4H-ch have numerous exciting biological activities, such as anticancer, anticonvulsant, antimicrobial, anticholinesterase, antituberculosis, and antidiabetic activities. This review is consequently an endeavor to highlight the diverse synthetic strategies, synthetic mechanism, various biological profiles, and SARs regarding the bioactive heterocycle, 2H/4H-ch. The presented scaffold work compiled in this article will be helpful to the scientific community for designing and developing potent leads of 2H/4H-ch analogs for their promising biological activities.

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Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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“…β-enaminonitriles containing 4H-benzo[h]chromene systems have been used in cancer treatment approaches; therefore, they are described as prospective cancer pharmaceuticals' targets. Examples include 2-amino/acetylamino substituents of 6-chloro/methoxy-4Hbenzo[h]chromenes that exhibited cytotoxic effects against MCF-7, HCT-116 and HepG-2 [9,20,21], as well as 2-amino and 2,7-diamino derivatives that showed anti-proliferative and c-Src kinase inhibitory effects [14,22]. Additionally, 1H-benzo[f ]chromene derivatives are advantageous for the creation of strong anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 9-Hydroxy-1H-Benzo[f]chromene Derivatives with Effective Cytotoxic Activity on MCF7/ADR, P-Glycoprotein Inhibitors, Cell Cycle Arrest and Apoptosis Effects

Albalawi

El-Nassag

El-Eisawy

et al. 2022

IJMS

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β-Enaminonitriles bearing 9-hydroxy-1H-benzo[f]chromene moiety was synthesized. The targeted compounds were evaluated for their anti-proliferative activity against three human tumor cell lines, PC-3, SKOV-3 and HeLa, and the active cytotoxic compounds were further evaluated against cancer cells, MCF-7/ADR, and two normal cell lines, HFL-1 and WI-38. Few compounds were assigned to be the most potent derivatives against PC-3, SKOV-3 and HeLa cell lines in comparison with Vinblastine and Doxorubicin. Several compounds possessed a relatively good potency against MCF-7/ADR cells as compared with Doxorubicin and were tested as a P-gp inhibitor. Moreover, the halogenated substituents, 2,4-F2, 2,3-Cl2, 2,5-Cl2 and 3,4-Cl2; have good potency against P-gp-mediated MDR in MCF-7/ADR as compared with Doxorubicin. Meanwhile, Rho123 accumulation assays revealed that few compounds effectively inhibited P-pg and efflux function. In addition, certain derivatives induced apoptosis and an accumulation of the treated MCF-7/ADR cells in the G1, S and G1/S phases.

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“…The comprehensive biomedical features of chromene molecules have motivated scientific figures within the drug discovery biosphere to cultivate new derivatives of this class of materials and explore their novel biological characteristics. Chromenes have been renowned for their incredible biological functions, which assisted their assimilation into various applications such as antimicrobial activities [10][11][12][13][14], hypolipidemic [15], antileishmanial, antiviral, anti-HIV, antianaphylactic activities [16][17][18], insecticidal [19], targeting of c-Src kinase enzyme [20,21], anticancer and cytotoxic activities [22][23][24][25], cell cycle analysis, apoptotic effects, caspase 3/7, and inhibition of the topoisomerase enzyme [26][27][28][29][30][31][32][33]. Among the synthetic strategies to acquire chromene molecules, microwave irradiation is one of the most efficacious and eco-friendly procedures, which facilitates the isolation of the desired compounds in a short period of time and results in good yields [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

The Crystal Structure of 3-Amino-1-(4-Chlorophenyl)-9-Methoxy-1H-Benzo[f]Chromene-2-Carbonitrile: Antimicrobial Activity and Docking Studies

et al. 2022

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Compound 3-amino-1-(4-chlorophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile (4), was synthesized via the reaction of 7-methoxynaphthalen-2-ol (1), 4-chlorobenzaldehyde (2), and malononitrile (3) in an ethanolic piperidine solution under microwave irradiation. The synthesized pyran derivative 4 was asserted through spectral data and X-ray diffraction. The molecular structure of compound 4 was established unambiguously through the single crystal X-ray measurements and crystallized in the Triclinic, P-1, a = 8.7171 (4) Å, b = 10.9509 (5) Å, c = 19.5853 (9) Å, α = 78.249 (2)°, β = 89.000 (2)°, γ = 70.054 (2)°, V = 1717.88 (14) Å3, Z = 4. The target molecule has been screened for antibacterial and antifungal functionality. Compound 4 exhibited favorable antimicrobial activities that resembled the reference antimicrobial agents with an IZ range of 16–26 mm. In addition, MIC, MBC, and MFC were assessed and screened for molecule 4, revealing bactericidal and fungicidal effects. Lastly, a molecular docking analysis was addressed and conducted for this desired molecule.

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Developing lipophilic aromatic halogenated fused systems with specific ring orientations, leading to potent anticancer analogs and targeting the c-Src Kinase enzyme

Cited by 34 publications

References 31 publications

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

Synthesis of 9-Hydroxy-1H-Benzo[f]chromene Derivatives with Effective Cytotoxic Activity on MCF7/ADR, P-Glycoprotein Inhibitors, Cell Cycle Arrest and Apoptosis Effects

The Crystal Structure of 3-Amino-1-(4-Chlorophenyl)-9-Methoxy-1H-Benzo[f]Chromene-2-Carbonitrile: Antimicrobial Activity and Docking Studies

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