Single-Crystal Structure and Antimicrobial Activity of Ethyl 3-Amino-1-(4-chlorophenyl)-9-hydroxy1H-benzo[f]chromene-2-carboxylate Combined with Ethyl α-Cyano-4-chlorocinnamate

Radwan, Hyam A.; El-Mawgoud, Heba Kamal Abd; El-Mariah, Fatma; El‐Agrody, Ahmed M.; Amr, Abd El‐Galil E.; Al-Omar, Mohamed A.; Ghabbour, Hazem A.

doi:10.1134/s107036322002022x

Cited by 4 publications

(8 citation statements)

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“…Some 3-amino-1aryl-1H-benzo[f]chromene-2-carbonitrile derivatives exhibit c-Src kinase inhibitory and antiproliferative activities [22] and show a high potency for the inhibition of hAChE [23], while inducing cell cycle arrest and apoptosis in human cancer cells via dual inhibition of topoisomerase I and II [26,27]. In continuation of our previous work in benzochromenes chemistry [2][3][4]22,26,27] and the study of crystal structure for benzochromene derivatives [2,[28][29][30][31][32][33][34], we report the synthesis, NMR spectra, crystal structure, theoretical calculations (DFT), molecular modeling analyses, and cytotoxic activity of 3-amino-1-(2,5-dichlorophenyl)-8-1H-benzo[f]chromene-2-carbonitrile.…”

Section: Introductionmentioning

confidence: 63%

“…Chromene and benzochromene derivatives represent an important class of oxygencontaining heterocyclic compounds. They exhibit a wide range of biological activities, such as antimicrobial [1][2][3][4], anti-influenza virus [5] anti-proliferative [6][7][8], anti-inflammatory, analgesic, and selective COX-2 inhibitory activities [9] and effects. Also, the small molecules of benzochromene derivatives apply their anticancer activities by binding to DNA, thereby damaging DNA structure, changing the replication of double helix DNA, hindering the division of cancer cells, and binding to DNA through covalent and/or noncovalent interactions [8,10].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

et al. 2021

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The target compound 3-amino-1-(2,5-d ichlorophenyl)-8-methoxy-1H-benzo[f]- chromene-2-carbonitrile (4) was synthesized via a reaction of 6-methoxynaphthalen-2-ol (1), 2,5-dichlorobenzaldehyde (2), and malononitrile (3) in ethanolic piperidine solution under microwave irradiation. The newly synthesized β-enaminonitrile was characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy, elemental analysis and X-ray diffraction data. Its cytotoxic activity was evaluated against three different human cancer cell lines MDA-MB-231, A549, and MIA PaCa-2 in comparison to the positive controls etoposide and camptothecin employing the XTT cell viability assay. The analysis of the Hirshfeld surface was utilized to visualize the reliability of the crystal package. The obtained results confirmed that the tested molecule revealed promising cytotoxic activities against the three cancer cell lines. Furthermore, theoretical calculations (DFT) were carried out with the Becke3-Lee-Yang-parr (B3LYP) level using 6-311++G(d,p) basis. The optimization geometry for molecular structures was in agreement with the X-ray structure data. The HOMO-LUMO energy gap of the studied system was discussed. The intermolecular-interactions were studied through analysis of the topological-electron-density(r) using the QTAIM and NCI methods. The novel compound exhibited favorable ADMET properties and its molecular modeling analysis showed strong interaction with DNA methyltransferase 1.

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Section: Introductionmentioning

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

et al. 2021

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“…The treatment of 2,7-dihydroxynapthalene with ethyl benzylidenecyanoacetate in an equimolar ratio under basic conditions afforded the benzo[ f ]chromene 1 in excellent yield (88%) via a convenient and high-yielding protocol ( Scheme 1 ). 24 The enaminoester chelation side was characterized using its IR spectrum, which showed the amino group absorption bands at 3410 and 3304 cm −1 and the ester C O stretching band at 1661 cm −1 . Moreover, the 1 H-NMR spectrum showed a broad singlet at δ 7.62 ppm, which is attributable to the NH 2 group, while the signals at δ 1.27 and 4.09 ppm are assignable to the ester methyl and methylene groups, respectively.…”

Section: Resultsmentioning

confidence: 99%

Selective and sensitive electrochemical sensors based on an ion imprinting polymer and graphene oxide for the detection of ultra-trace Cd(ii) in biological samples

et al. 2021

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“…Because of their structural diversity, the nuclei of chromene and benzochromene have emerged as a promising and appealing scaffold in the development of antimicrobial and antitumor agents 2 – 31 . Specifically, a number of investigations have demonstrated the antimicrobial properties of benzochromene derivatives 2 – 6 .…”

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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Single-Crystal Structure and Antimicrobial Activity of Ethyl 3-Amino-1-(4-chlorophenyl)-9-hydroxy1H-benzo[f]chromene-2-carboxylate Combined with Ethyl α-Cyano-4-chlorocinnamate

Cited by 4 publications

References 11 publications

Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Selective and sensitive electrochemical sensors based on an ion imprinting polymer and graphene oxide for the detection of ultra-trace Cd(ii) in biological samples

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

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