Synthesis of certain novel 4H-pyrano[3,2-h]quinoline derivatives

El‐Agrody, Ahmed M.; Al-Ghamdi, Abdullah M.

doi:10.3998/ark.5550190.0012.b12

Cited by 27 publications

(5 citation statements)

References 8 publications

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“…We report here the synthesis, antimicrobial and cytotoxic activities of 3-amino-1-aryl-8-methoxy-1 H -benzo[ f ]chromene-2-carbonitrile derivatives, as a continuation of our ongoing research efforts for potent oxygen–nitrogen-heterocyclic-based with effective cytotoxic and antimicrobial activities 35 – 48 .…”

Section: Introductionmentioning

confidence: 99%

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

El-Wahab,

Borik,

Al-Dies

et al. 2024

Sci Rep

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The process of creating a series of 3-amino-1-aryl-8-methoxy-1H-benzo[f]chromene-2-carbonitriles (4a-q) involved reacting 6-methoxynaphthalen-2-ol (1), the appropriate aromatic aldehydes (2a-q), and malononitrile (3) in an absolute ethanol/piperidine solution under Ultrasonic irradiation. However, the attempt to create 3-amino-1-aryl-1H-benzo[f]chromene-2,8-dicarbonitrile (6a, d, e) was unsuccessful when 6-cyanonaphthalen-2-ol (5) was stirred at room temperature, reflux, Microwave irradiation, or Ultrasonic irradiation. In addition, the target molecules were screened against Staphylococcus aureus (MRSA), Staphylococcus aureus, Bacillus subtilis, Bacillus cereus, Escherichia coli and Klebsiella pneumonia, as well as a panel of three human cancer cells lines such as MCF-7, HCT-116, HepG-2 and two normal cell lines HFL-1 and WI-38. The obtained results confirmed that the pyran derivatives (4 m, i, k) which have a double chlorine at 3,4/2,3/2,5-positions, a single halogen atom 3-Cl/4-Br (4c, e) and a double bromine at 3,5-positions with a single methoxy group at 2-position (4n), of phenyl ring, and, to a lesser extent, other pyran derivatives with monoihalogenated (4a, b, d, f), dihalogenated (4 g, h, j, l) or trisubstituent phenyl ring (4o, p, q). Furthermore, compounds 4b-e, g, i, j, m, and n showed negligible activity against the two normal cell lines, HFL-1 and WI-38. Moreover, compound 4 g exhibited the strongest antimicrobial activity among the other pyran derivatives (4a-f, g-q) when compared to Ciprofloxacin. The MIC was assessed and screened for compound 4 g, revealing bactericidal effects. Lastly, SAR and molecular docking were studied.

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Section: Introductionmentioning

confidence: 99%

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

El-Wahab,

Borik,

Al-Dies

et al. 2024

Sci Rep

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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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“…4-Hydroxyquinolin-2(1H)-ones represents one of the most important class of heterocycles possessing wide spectrum of biological activities [1][2][3][4][5][6]. Also, they have occupied a unique place in the medicinal and biological chemistry due to their diverse pharmacological displays as antitumor [7], antimicrobial [8], antibacterial [9] and antischistosomal agents [10].They are also useful intermediates in the manufacture of azo dyestuffs,that can be used for dyeing both naturally occurring and synthetic fibres [11] .…”

Section: Introductionmentioning

confidence: 99%

Studies on Quinolin-2(1H)-One Derivatives: Synthetic Access to Pyrano[3,2-c] Quinoline and 3-Substituted Quinoline Derivatives

El‐Taweel

2013

ACSJ

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Synthesis of certain novel 4H-pyrano[3,2-h]quinoline derivatives

Cited by 27 publications

References 8 publications

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

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

Studies on Quinolin-2(1H)-One Derivatives: Synthetic Access to Pyrano[3,2-c] Quinoline and 3-Substituted Quinoline Derivatives

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