Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 

Saved Queries

Sign in to use this feature.

Search Filter Reset All

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Subjects Reset
Select Subjects

Journals

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Journals Reset
Select Journals

Article Types

remove_circle_outline
remove_circle_outline
Add Article Types Reset
Select Article Types

Countries / Regions

remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Countries / Regions Reset
Select Countries / Regions
Update Search
share announcement

Search Results (6)

Search Parameters:
Keywords = β-enaminonitrile

Order results
Result details
Results per page
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
10 pages, 780 KiB  
Article
Facile Synthesis of Polysubstituted Pyridines via Metal-Free [3+3] Annulation Between Enamines and β,β-Dichloromethyl Peroxides
by Yangyang Ma, Hua Zhang, Zhonghao Zhou, Chenyang Yang, Wenxiao Chang, Mohan Li, Yapei Zheng, Weizhuang Zhang, Huan Yue, Changdong Chen, Ming La and Yongjun Han
Int. J. Mol. Sci. 2025, 26(15), 7105; https://doi.org/10.3390/ijms26157105 - 23 Jul 2025
Viewed by 350
Abstract
Our work introduces a facile and efficient metal-free [3+3] annulation approach for the synthesis of polysubstituted pyridines via the reaction between β-enaminonitriles and β,β-dichloromethyl peroxides. This strategy operates under mild conditions, demonstrating broad substrate scope and excellent functional group tolerance. Mechanistic investigations suggest [...] Read more.
Our work introduces a facile and efficient metal-free [3+3] annulation approach for the synthesis of polysubstituted pyridines via the reaction between β-enaminonitriles and β,β-dichloromethyl peroxides. This strategy operates under mild conditions, demonstrating broad substrate scope and excellent functional group tolerance. Mechanistic investigations suggest that the reaction proceeds through a Kornblum–De La Mare rearrangement followed by SNV-type C-Cl bond cleavage and intramolecular cyclization/condensation. By circumventing the need for transition metal catalysts or radical initiators, our method offers practical utility in organic synthesis and provides a new avenue for the rapid construction of complex pyridine scaffolds. Full article
(This article belongs to the Section Physical Chemistry and Chemical Physics)
►▼ Show Figures

Figure 1

17 pages, 7604 KiB  
Article
Synthesis, Cytotoxic Activity, Crystal Structure, DFT, Molecular Docking Study of β-Enaminonitrile Incorporating 1H-Benzo[f]Chromene Moiety
by Mosa H. Alsehli, Lali M. Al-Harbi, Rawda M. Okasha, Ahmed M. Fouda, Hazem A. Ghabbour, Abd El-Galil E. Amr, Ahmed A. Elhenawy and Ahmed M. El-Agrody
Crystals 2023, 13(1), 24; https://doi.org/10.3390/cryst13010024 - 23 Dec 2022
Cited by 10 | Viewed by 2223
Abstract
In this work, we used microwave irradiation conditions to synthesize β-enaminonitrile (4), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL-1 [...] Read more.
In this work, we used microwave irradiation conditions to synthesize β-enaminonitrile (4), which was affirmed using single crystal X-ray diffraction and the different spectral data. Two tumor cell lines, MCF-7 and MCF-7/ADR, as well as two normal cell lines, HFL-1 and WI-38, were used to assess the anticancer activity of compound 4. The studied molecule exhibited potent efficacy against the MCF-7 and MCF-7/ADR cell lines compared with the reference drugs. Furthermore, target compound 4 had feeble activity against HFL-1 and WI-38. The chemical reactivity was discussed using DFT and QTAIM analysis to study the intrinsic electronic properties of compound 4. A molecular docking study was also conducted to examine their binding affinity to the EGFR. Compound 4 revealed a stable binding mode at the enzyme active pocket more than the reference inhibitor. The docking analysis was performed for molecule (4). Full article
(This article belongs to the Special Issue Frontiers of Applied Crystal Chemistry)
►▼ Show Figures

Figure 1

22 pages, 4080 KiB  
Article
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
by Fawzia F. Albalawi, Mohammed A. A. El-Nassag, Raafat A. El-Eisawy, Mahmoud Basseem I. Mohamed, Ahmed M. Fouda, Tarek H. Afifi, Ahmed A. Elhenawy, Ahmed Mora, Ahmed M. El-Agrody and Heba K. A. El-Mawgoud
Int. J. Mol. Sci. 2023, 24(1), 49; https://doi.org/10.3390/ijms24010049 - 20 Dec 2022
Cited by 10 | Viewed by 3289
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Section Molecular Toxicology)
►▼ Show Figures

Figure 1

6 pages, 3861 KiB  
Proceeding Paper
Computational Revision of the Mechanism of the Thorpe Reaction
by Victor A. Lucas-Rosales, Marco A. García-Revilla and J. Oscar C. Jiménez-Halla
Chem. Proc. 2022, 12(1), 29; https://doi.org/10.3390/ecsoc-26-13550 - 14 Nov 2022
Viewed by 2388
Abstract
The Thorpe reaction is described as a self-condensation of nitriles in the presence of a basic catalyst producing β-enaminonitriles. We performed theoretical calculations within the Density Functional Theory (DFT) framework at the ωB97XD/def2-svpd level to explore different mechanistic proposals when propionitrile is used [...] Read more.
The Thorpe reaction is described as a self-condensation of nitriles in the presence of a basic catalyst producing β-enaminonitriles. We performed theoretical calculations within the Density Functional Theory (DFT) framework at the ωB97XD/def2-svpd level to explore different mechanistic proposals when propionitrile is used as a reagent and sodium ethoxide (EtONa) as a catalyst. Furthermore, the influence of different solvents, such as ethanol (EtOH), tetrahydrofuran (THF), 1,2-dimethoxyethane (DME), and propionitrile (EtCN), was assessed. Finally, we also evaluated the effect of the fluorine group (-F), compared to the methyl group (-CH3), substituted in the α position of acetonitrile (MeCN). Our theoretical findings agree with different experimental reports on the Thorpe reaction. Full article
(This article belongs to the Proceedings of The 26th International Electronic Conference on Synthetic Organic Chemistry)
►▼ Show Figures

Figure 1

17 pages, 7061 KiB  
Article
The Crystal Structure of 2-Amino-4-(2,3-Dichlorophenyl)-6-Methoxy-4H-Benzo[h]chromene-3-Carbonitrile: Antitumor and Tyrosine Kinase Receptor Inhibition Mechanism Studies
by Ahmed M. El-Agrody, Ahmed M. Fouda, Hany M. Mohamed, Mohammed Y. Alshahrani, Hazem A. Ghabbour, Abd El-Galil E. Amr, Rawda M. Okasha, Ahmed M. Naglah, Abdulrahman A. Almehizia and Ahmed A. Elhenawy
Crystals 2022, 12(5), 737; https://doi.org/10.3390/cryst12050737 - 20 May 2022
Cited by 8 | Viewed by 3184
Abstract
The target compound, 2-amino-4-(2,3-dichlorophenyl)-6-methoxy-4H-benzo[h]chromene -3-carbonitrile (4), was synthesized via the reaction of 4-methoxynaphthalen-1-ol (1), 2,3-dichlorobenzaldehyde (2), and malononitrile (3) in an ethanolic piperidine solution under microwave irradiation. The synthesized β-enaminonitrile derivative (4) was characterized by [...] Read more.
The target compound, 2-amino-4-(2,3-dichlorophenyl)-6-methoxy-4H-benzo[h]chromene -3-carbonitrile (4), was synthesized via the reaction of 4-methoxynaphthalen-1-ol (1), 2,3-dichlorobenzaldehyde (2), and malononitrile (3) in an ethanolic piperidine solution under microwave irradiation. The synthesized β-enaminonitrile derivative (4) was characterized by spectral data and X-ray diffraction. The in vitro anti-proliferative profile was conducted against five cancer cell lines and was assessed for compound 4, which revealed strong and selective cytotoxic potency. This derivative showed promising inhibition efficacy against the EGFR and VEGFR-2 kinases in comparison to Sorafenib as a reference inhibitor. Lastly, the docking analysis into the EGFR and VEGFR-2 active sites was performed to clarify our biological findings. Full article
(This article belongs to the Special Issue Novel Nanomaterials for Catalytic and Biological Applications)
►▼ Show Figures

Figure 1

22 pages, 6359 KiB  
Article
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
by Menna El Gaafary, Tatiana Syrovets, Hany M. Mohamed, Ahmed A. Elhenawy, Ahmed M. El-Agrody, Abd El-Galil E. Amr, Hazem A. Ghabbour and Abdulrahman A. Almehizia
Crystals 2021, 11(2), 184; https://doi.org/10.3390/cryst11020184 - 13 Feb 2021
Cited by 36 | Viewed by 6030
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue A 10 Years Journey: Chemical, Physical, and Biological Properties and Applications of Crystals)
►▼ Show Figures

Figure 1

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying article 1-50 on page 1 of 1.
Back to TopTop