Synthesis and antitumor activities of certain novel 2-amino-9-(4-halostyryl)-4H-pyrano[3,2-h]quinoline derivatives

El‐Agrody, Ahmed M.; Khattab, Essam Shawky A. E. H.; Fouda, Ahmed M.; Al-Ghamdi, Abdullah M.

doi:10.1007/s00044-011-9965-x

Cited by 28 publications

(3 citation statements)

References 38 publications

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“…The multidrug-resistant phenotype in cancer that mediates MDR also heavily relies on P-glycoprotein (P-gp/ABCB1) [29]. Based on our ongoing experiences to create effective anticancer benzochromenebased medicines, [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48], we have initiated the current study. Developing drugs with potential anti-proliferative activity against three cancer cell lines, PC-3, SKOV-3 and HeLa, while having no cytotoxic effect on normal cell lines HFL-1 and WI-38, was the main motivation behind our decision to design and synthesize β-enaminonitriles incorporating a 9-hydroxy-1H-benzo[f]chromene moiety.…”

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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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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“…In continuation of our efforts to discover oxygen-heterocyclic derivatives with promising antimicrobial and antitumor activities [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57], we present the synthesis of 3-amino-1-(4-chlorophenyl)-9-methoxy-1H-benzo[f ]chromene-2-carbonitrile and portray its crystallographic structure. Moreover, the antimicrobial behavior of the target molecule is evaluated and its minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentrations (MFC) are appraised.…”

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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“…El‐Agrody et al . reported a similar kind of reaction leading to 2‐styryl‐8‐hydroxyquinolines, the compounds with significant antitumor activity . Each of these reported procedures has its own merit, but all suffer from limitation of the synthesis to only a narrow range of pyrano[3,2‐ h ]quinolines, a difficulty to isolate products or long reaction time and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

InCl₃ Promoted Synthesis of Pyrano[3,2‐h]quinolines via Microwave Irradiation

Kumar

Zeller

Frasso

et al. 2014

Journal of Heterocyclic Chem

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Synthesis and antitumor activities of certain novel 2-amino-9-(4-halostyryl)-4H-pyrano[3,2-h]quinoline derivatives

Cited by 28 publications

References 38 publications

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

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

InCl₃ Promoted Synthesis of Pyrano[3,2‐h]quinolines via Microwave Irradiation

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Synthesis and antitumor activities of certain novel 2-amino-9-(4-halostyryl)-4H-pyrano[3,2-h]quinoline derivatives

Cited by 28 publications

References 38 publications

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

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

InCl3 Promoted Synthesis of Pyrano[3,2‐h]quinolines via Microwave Irradiation

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InCl₃ Promoted Synthesis of Pyrano[3,2‐h]quinolines via Microwave Irradiation