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, Fawzia F; El-Nassag, Mohammed A. A.; El-Eisawy, R.A.; Mohamed, Mahmoud Basseem I.; Fouda, Ahmed M.; Afifi, Tarek H.; Elhenawy, Ahmed A.; Mora, Ahmed; El‐Agrody, Ahmed M.; El-Mawgoud, Heba Kamal Abd

doi:10.3390/ijms24010049

Cited by 6 publications

(6 citation statements)

References 68 publications

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“…7). The bioactivity indices LE and Ki were also all within the expected range [44,45]. It is clear that molecular docking promoted antibacterial activity, which had an impact on the effectiveness of the docking experiment.…”

Section: Molecular Docking Pro Lementioning

confidence: 68%

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

Ouzidan,

Hjouji,

Hafez

et al. 2024

Preprint

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6-Bromo-2-phenyl-1,3,4-triazaindan under solid-liquid catalysis-transfer-phase(CTP) environment, pyridine interacts with a number of halogenated derivatives to produce the anticipated regioisomer molecules 2a and 2b. Besides, the reaction of compound (1) with bis(2-chloroethyl) amine results in the corresponding isoxazolidin-2-one derivatives (3a) and (3b) at a satisfactory yield. The synthesized compounds are confirmed by X-ray diffraction, spectral techniques (1H NMR, 13C NMR). Then, 1,3,4-Triaza-3H-indene derivatives were analyzed in silico based on molecular structure by molecular docking analysis to determine which one could be used for in vitro antibacterial activity testing. The compounds with the highest binding efficiency in the docking experiment were chosen to be evaluated against both Gram-positive and Gram-negative bacteria. These compounds showed higher efficacy against Gram-positive bacteria than Gram-negative bacteria, which are much more resistant to them.

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Section: Molecular Docking Pro Lementioning

confidence: 68%

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

Ouzidan,

Hjouji,

Hafez

et al. 2024

Preprint

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“…The antiproliferative activity of the newly synthesized 1 H -benzo[ f ]chromenes derivatives ( 4a-q ) was examined in three human cancer cell lines: MCF-7 (breast cancer), HCT-116 (human colon cancer), and HepG-2 (hepatocellular carcinoma), as well as the two normal cell lines, HFL-1 (human foetal lung) and WI-38 (human diploid fibroblasts), using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) colorimetric assay 56 . The selection of these particular cell lines, MCF-7, HCT-116 and HepG-2 was stimulated by the affirmed antiproliferative activity of reported chromene and fused chromene derivatives 7 – 34 . The three cell lines used in the experiments were exposed to reference cytotoxic compound, Erlotinib.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, 1 H -benzo[ f ]chromene derivatives are regarded as promising lead candidates for anticancer drug development. For example, 9-hydroxy/methoxy of 1 H -benzo[ f ]chromene derivatives ( N ) effective cytotoxic activity on MCF7/ADR, P -Glycoprotein inhibitors, Cell cycle arrest and apoptosis effects 7 , 8 , 1 H -benzo[ f ]chromene derivatives and 8-bromo/methoxy derivative of 1 H -benzo[ f ]chromenes (O) exhibited c-Src kinase inhibitory and proapoptotic activities 24 , 25 . A series of 1-substituted aryl-2-(1 H -tetrazol-5-yl)-1 H -benzo[ f ]chromene-3-amines (P) derivatives 27 , some derivatives of 3,5-diamino and 3-amino of 1 H -benzo[ f ]chromene-2-carbonitrile (Q) , have been reported to exhibit cytotoxic and apoptotic effects against a variety of human cancer cell lines 17 , 28 , 29 .…”

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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“…6-bromo-2-phenyl-3-(p-tolyl)-3H-imidazo[4,5-b]pyridine ( 2 ) formed an extra π–π bond with Tyr22, while ethyl 6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine-3-carboxylate ( 6 ) formed two strong H-bonds with Asn64 and Arg70 ( Figure 10 ). In addition, all the bioactivity metrics LE and Ki were within a normal range for 1 – 8 [ 47 ]. It can be inferred that the molecular docking encourages us to perform antimicrobial activity against most binding efficiencies in the docking experiment.…”

Section: Resultsmentioning

confidence: 99%

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

et al. 2023

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5-bromopyridine-2,3-diamine reacted with benzaldehyde to afford the corresponding 6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (1). The reaction of the latter compound (1) with a series of halogenated derivatives under conditions of phase transfer catalysis solid–liquid (CTP) allows the isolation of the expected regioisomers compounds (2–8). The alkylation reaction of (1) gives, each time, two regioisomers, N3 and N4; in the case of ethyl bromoactate, the reaction gives, at the same time, the three N1, N3 and N4 regioisomers. The structures of synthesized compounds were elucidated on the basis of different spectral data (1H NMR, 13C NMR), X-Ray diffraction and theoretical study using the DFT method, and confirmed for each compound. Hirshfeld surface analysis was used to determine the intermolecular interactions responsible for the stabilization of the molecule. Density functional theory was used to optimize the compounds, and the HOMO-LUMO energy gap was calculated, which was used to examine the inter/intra molecular charge transfer. The molecular electrostatic potential map was calculated to investigate the reactive sites that were present in the molecule. In order to determine the potential mode of interactions with DHFR active sites, the three N1, N3 and N4 regioisomers were further subjected to molecular docking study. The results confirmed that these analogs adopted numerous important interactions, with the amino acid of the enzyme being targeted. Thus, the most docking efficient molecules, 2 and 4, were tested in vitro for their antibacterial activity against Gram-positive bacteria (Bacillus cereus) and Gram-negative bacteria (Escherichia coli). Gram-positive bacteria were more sensitive to the action of these compounds compared to the Gram-negative, which were much more resistant.

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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

Cited by 6 publications

References 68 publications

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

New 1,3,4-Triaza-3H-indene Derivatives in Theoretical, Experimental and biological Studies

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

Exploring Antimicrobial Features for New Imidazo[4,5-b]pyridine Derivatives Based on Experimental and Theoretical Study

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