3-Amino-1-(4-fluorophenyl)-8-methoxy-1<i>H</i>-benzo[<i>f</i>]chromene-2-carbonitrile

El‐Agrody, Ahmed M.; Al-Omar, Mohamed A.; Amr, Abd El‐Galil E.; Ng, Seik Weng; Tiekink, Edward R. T.

doi:10.1107/s160053681300545x

Cited by 5 publications

(3 citation statements)

References 10 publications

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“…Spectral data verified the structure and purity of the synthesis compounds 4a-q , and single crystal X-ray analysis of compounds 4 k, a, e, h, j, and n 42 , 49 – 53 offered a definitive confirmation for the desired molecules (refer to the Supplementary data ).…”

Section: Resultssupporting

confidence: 54%

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: Resultssupporting

confidence: 54%

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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“…Literature reveals that chromenes and benzochromenes are an important chemical synthon, associated with a broad range of pharmacological activities such as antimicrobial [2][3][4][5], anticancer agent [6] hypolipidemic [7], antioxidant [8,9], analgesic [10], antileishmanial [11,12], vascular-disrupting activity [13], estrogenic anticoagulant and antispasmolytic [14], blood platelet antiaggregating [15] effects and activities. As part of our programmed aim to develop new methodologies for the preparation of 1H-benzo[f ]chromene derivatives [16][17][18], we have synthesized the title compound under microwave irradiation conditions. In the title compound, the asymmetric unit of the title compound contains one independent molecule.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C₂₂H₁₈N₂O₃

Fouda¹,

Amr

El‐Agrody

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The crystalline configurations of drug candidates have amassed substantial appreciation as a critical criterion for rational drug design with the manipulation of their functional moieties impacting the drug's structure-activity relationship. Generally, the attained crystallographic data offer explicit/precise structural identification and absolute configuration [1][2][3][4][5][6], which accordingly elucidates the performance of the novel drugs without triggering the adverse response of the biological system stimuli. Of the drug candidates with an elevated disposition to forge crystallographic structures, chromene compounds are among the most notorious and prosperous [7][8][9].…”

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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3-Amino-1-(4-fluorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Abstract: Key indicators: single-crystal X-ray study; T = 295 K; mean (C-C) = 0.003 Å; R factor = 0.049; wR factor = 0.138; data-to-parameter ratio = 16.0.

Cited by 5 publications

References 10 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

Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C₂₂H₁₈N₂O₃

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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3-Amino-1-(4-fluorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Abstract: Key indicators: single-crystal X-ray study; T = 295 K; mean (C-C) = 0.003 Å; R factor = 0.049; wR factor = 0.138; data-to-parameter ratio = 16.0.

Cited by 5 publications

References 10 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

Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3

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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Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C₂₂H₁₈N₂O₃