3-Alkenyl-2-oxindoles: Synthesis, antiproliferative and antiviral properties against SARS-CoV-2
Author's Department
Institute of Global Health & Human Ecology
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https://doi.org/10.1016/j.bioorg.2021.105131
Document Type
Research Article
Publication Title
Bioorganic chemistry
Publication Date
7-10-2021
doi
10.1016/j.bioorg.2021.105131
Abstract
Sets of 3-alkenyl-2-oxindoles (6,10,13) were synthesized in a facile synthetic pathway through acid dehydration (EtOH/HCl) of the corresponding 3-hydroxy-2-oxoindolines (5,9,12). Single crystal (10a,c) and powder (12a,26f) X-ray studies supported the structures. Compounds 6c and 10b are the most effective agents synthesized (about 3.4, 3.3 folds, respectively) against PaCa2 (pancreatic) cancer cell line relative to the standard reference used (Sunitinib). Additionally, compound 10b reveals antiproliferative properties against MCF7 (breast) cancer cell with IC close to that of Sunitinib. CAM testing reveals that compounds 6 and 10 demonstrated qualitative and quantitative decreases in blood vessel count and diameter with efficacy comparable to that of Sunitinib, supporting their anti-angiogenic properties. Kinase inhibitory properties support their multi-targeted inhibitory activities against VEGFR-2 and c-kit in similar behavior to that of Sunitinib. Cell cycle analysis studies utilizing MCF7 exhibit that compound 6b arrests the cell cycle at G1/S phase while, 10b reveals accumulation of the tested cell at S phase. Compounds 6a and 10b reveal potent antiviral properties against SARS-CoV-2 with high selectivity index relative to the standards (hydroxychloroquine, chloroquine). Safe profile of the potent synthesized agents, against normal cells (VERO-E6, RPE1), support the possible development of better hits based on the attained observations.
First Page
105131
Last Page
105131
Recommended Citation
APA Citation
Girgis, A. S.
Panda, S. S.
Srour, A. M.
&
Abdelnaser, A.
(2021). 3-Alkenyl-2-oxindoles: Synthesis, antiproliferative and antiviral properties against SARS-CoV-2. Bioorganic chemistry, 114([not provided]), 105131–105131.
10.1016/j.bioorg.2021.105131
https://fount.aucegypt.edu/faculty_journal_articles/2286
MLA Citation
Girgis, Adel, et al.
"3-Alkenyl-2-oxindoles: Synthesis, antiproliferative and antiviral properties against SARS-CoV-2." Bioorganic chemistry, vol. 114,no. [not provided], 2021, pp. 105131–105131.
https://fount.aucegypt.edu/faculty_journal_articles/2286