X-ray, Microwave Assisted Synthesis and Spectral Data of 3-Amino-1-(3,5-dibromo-2-methoxy phenyl)-8-methoxy-1<i>H</i>-benzo[<i>f</i>]chromene-2-carbonitrile

Amr, Abd El‐Galil E.; El-Mawgoud, Heba Kamal Abd; El‐Agrody, Ahmed M.; Al-Omar, Mohamed A.; Alsultan, Mohamed S.

doi:10.1166/jctn.2017.6696

Cited by 5 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further assignment of the structures of compounds 4b, 4c, 4f, 4g, 4i, 4l, 4m, and 4o–4q was accomplished by mass spectra. The 13 C-NMR-DEPT for compound 4p and the single crystal x-ray structure analysis of compounds 4h, 4j, 4k, and 4n gave an absolute confirmation for the structures ( Amr et al, 2017 ; Halawa et al, 2017 ; Okasha et al, 2017 ; El Gaafary et al, 2021 ). The 1 H-NMR and 13 C-NMR spectra of the synthesized compounds are presented in the Supplementary Data ( Supplementary Figures S1–S45 ).…”

Section: Resultsmentioning

confidence: 83%

See 1 more Smart Citation

Synthesis of β-Enaminonitrile-Linked 8-Methoxy-1H-Benzo[f]Chromene Moieties and Analysis of Their Antitumor Mechanisms

et al. 2021

View full text Add to dashboard Cite

A series of aryl-substituted 3-amino-1-aryl-8-methoxy-1H-benzo[f]chromene-2-carbonitriles (4a–4q) were designed and synthesized via reaction of 6-methoxy-2-naphthol with a mixture of appropriate aromatic aldehydes and malononitrile under microwave conditions. The structures of the novel compounds 4b, 4c, 4f, 4g, 4i, 4l, 4m, and 4o–4q were established according to IR, 1H-NMR, 13C-NMR/13C-NMR-DEPT, and MS. The benzochromene derivative 4c with a single chlorine at the meta position of the phenyl ring and, to a lesser extent, other benzochromenes with monohalogenated phenyl ring (4a, 4c–4f) exhibited the highest cytotoxicity against six human cancer cell lines MDA-MB-231, A549, HeLa, MIA PaCa-2, 5,637, and Hep G2. The mechanisms of the cytotoxic activities of benzochromenes with monohalogenated phenyl ring (4a, 4c–4f) were further analyzed using triple-negative breast cancer cell line MDA-MB-231. Cell cycle analysis showed accumulation of the treated cells in S phase for 4a, 4d–4f, and S-G2/M phases for 4c. In vivo, 4a and 4c–4f inhibited growth, proliferation, and triggered apoptosis in preestablished breast cancer xenografts grown on the chick chorioallantoic membranes while exhibiting low systemic toxicity. Compounds 4a and 4c–4f increased levels of mitochondrial superoxide and decreased mitochondrial membrane potential resulting in initiation of apoptosis as demonstrated by caspase 3/7 activation. In addition, 4c induced general oxidative stress in cancer cells. The SAR study confirmed that halogens of moderate size at meta or para positions of the pendant phenyl ring enhance the cytotoxic activity of 3-amino-1-aryl-8-methoxy-1H-benzo[f]chromene-2-carbonitriles, and these compounds could serve as leads for the development of novel anticancer therapies.

show abstract

Section: Resultsmentioning

confidence: 83%

“…3-Amino-1-(3,5-dibromo-2-methoxyphenyl)-8-methoxy-1 H -benzo[ f ]chromene-2-carbonitrile (4n). Compound 4n was prepared according to the literature procedure ( Amr et al, 2017 ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of β-Enaminonitrile-Linked 8-Methoxy-1H-Benzo[f]Chromene Moieties and Analysis of Their Antitumor Mechanisms

et al. 2021

View full text Add to dashboard Cite

show abstract

“…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: 85%

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

View full text Add to dashboard Cite

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.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

X-ray, Microwave Assisted Synthesis and Spectral Data of 3-Amino-1-(3,5-dibromo-2-methoxy phenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Cited by 5 publications

References 0 publications

Synthesis of β-Enaminonitrile-Linked 8-Methoxy-1H-Benzo[f]Chromene Moieties and Analysis of Their Antitumor Mechanisms

Synthesis of β-Enaminonitrile-Linked 8-Methoxy-1H-Benzo[f]Chromene Moieties and Analysis of Their Antitumor Mechanisms

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

The Crystal Structure of 3-Amino-1-(4-Chlorophenyl)-9-Methoxy-1H-Benzo[f]Chromene-2-Carbonitrile: Antimicrobial Activity and Docking Studies

Contact Info

Product

Resources

About