Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR

Eliwa EM, Frese M, Halawa AH, Soltan MM, Ponomareva LV, Thorson JS, Shaaban KA, Shaaban M, El-Agrody AM, Sewald N (2021)
Green Chemistry Letters and Reviews 14(4): 576-597.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Eliwa, Essam M.; Frese, MarcelUniBi ; Halawa, Ahmed H.; Soltan, Maha M.; Ponomareva, Larissa V.; Thorson, Jon S.; Shaaban, Khaled A.; Shaaban, Mohamed; El-Agrody, Ahmed M.; Sewald, NorbertUniBi
Abstract / Bemerkung
A metal-free, atom-economy and simple work-up domino amination-Knoevenagel condensation approach to construct new coumarin analogous (4a-f and 8a-e) was described. Further, new formyl (5a,d-f) and nitro (9a,d-f) coumarin derivatives were synthesized via C-N coupling reaction of various cyclic secondary amines and 4-chloro-3-(formyl-/nitro)coumarins (1a,c), respectively. The confirmed compounds were screened for their in vitro anti-proliferative activity against KB-3-1, A549 and PC3 human cancer cell lines using resazurin cellular-based assay. Among them, coumarin derivatives 4e and 8e displayed the best anti-cervical cancer potency (KB-3-1) with IC50 values of 15.5 ± 3.54 and 21 ± 4.24 µM, respectively. Also, 4e showed the most promising cytotoxicity toward A549 with IC50 value of 12.94 ± 1.51 µM. As well, 9d presented a more significant impact of potency against PC3 with IC50 7.31 ± 0.48 µM. Moreover, 8d manifested selectivity against PC3 (IC50 = 20.16 ± 0.07 µM), while 8e was selective toward KB-3-1 cell line (IC50 = 21 ± 4.24 µM). Matching with docking profile, the enzymatic assay divulged that 8e is a dual potent single-digit nanomolar inhibitor of VEGFR-2 and EGFR with IC50 values of 24.67 nM and 31.6 nM that were almost equipotent to sorafenib (31.08 nM) and erlotinib (26.79 nM), respectively.
Erscheinungsjahr
2021
Zeitschriftentitel
Green Chemistry Letters and Reviews
Band
14
Ausgabe
4
Seite(n)
576-597
ISSN
1751-8253
eISSN
1751-7192
Page URI
https://pub.uni-bielefeld.de/record/2957723

Zitieren

Eliwa EM, Frese M, Halawa AH, et al. Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR. Green Chemistry Letters and Reviews. 2021;14(4):576-597.
Eliwa, E. M., Frese, M., Halawa, A. H., Soltan, M. M., Ponomareva, L. V., Thorson, J. S., Shaaban, K. A., et al. (2021). Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR. Green Chemistry Letters and Reviews, 14(4), 576-597. https://doi.org/10.1080/17518253.2021.1981462
Eliwa, E. M., Frese, M., Halawa, A. H., Soltan, M. M., Ponomareva, L. V., Thorson, J. S., Shaaban, K. A., Shaaban, M., El-Agrody, A. M., and Sewald, N. (2021). Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR. Green Chemistry Letters and Reviews 14, 576-597.
Eliwa, E.M., et al., 2021. Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR. Green Chemistry Letters and Reviews, 14(4), p 576-597.
E.M. Eliwa, et al., “Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR”, Green Chemistry Letters and Reviews, vol. 14, 2021, pp. 576-597.
Eliwa, E.M., Frese, M., Halawa, A.H., Soltan, M.M., Ponomareva, L.V., Thorson, J.S., Shaaban, K.A., Shaaban, M., El-Agrody, A.M., Sewald, N.: Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR. Green Chemistry Letters and Reviews. 14, 576-597 (2021).
Eliwa, Essam M., Frese, Marcel, Halawa, Ahmed H., Soltan, Maha M., Ponomareva, Larissa V., Thorson, Jon S., Shaaban, Khaled A., Shaaban, Mohamed, El-Agrody, Ahmed M., and Sewald, Norbert. “Metal-free domino amination-Knoevenagel condensation approach to access new coumarins as potent nanomolar inhibitors of VEGFR-2 and EGFR”. Green Chemistry Letters and Reviews 14.4 (2021): 576-597.

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