Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety

Halawa AH, Abd El-Gilil SM, Bedair AH, Shaaban M, Frese M, Sewald N, Eliwa EM, El-Agrody AM (2017)
Zeitschrift für Naturforschung C 72(11-12): 467-475.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Halawa, Ahmed H.; Abd El-Gilil, Shimaa Mohamed; Bedair, Ahmed H.; Shaaban, Mohamed; Frese, MarcelUniBi ; Sewald, NorbertUniBi ; Eliwa, Essam M.; El-Agrody, Ahmed M.
Einrichtung
Fakultät für Chemie > Organische Chemie III
Abstract / Bemerkung
A new series of heterocyclic Schiff bases 2-9 containing indole moiety were synthesized by facile and efficient condensation of indole-3/2/5-carboxaldehyde (1a/1b/1c) with different aromatic and heterocyclic primary amines using conventional and/or microwave irradiation methods. The structures of the obtained compounds were assigned by sophisticated spectroscopic and spectrometric techniques (1D-NMR, 2D-NMR and MS). The synthesized compounds were screened for their cytotoxicity and antibacterial activities. In vitro cytotoxicity screening revealed that compound 5 exhibited moderate activity against KB-3-1 cell line (IC50 = 57.7 mu M) while 5-indolylimino derivative 7 indicated close to the activity (IC50 = 19.6 mu M) in comparison with the positive control (+)-Griseofulvin (IC50 = 19.2 mu M), while the tested compounds 5, 6b, 7 and 9 revealed good or moderate antibacterial activity. In addition, molecular docking study of Schiff bases 2-9 was performed by Molecular Operating Environment (MOE 2014.09) program on the matrix metalloproteinase-8 (MMP-8) (Protein Data Bank (PDB) ID: 1MNC) in an attempt to explore their mode of action as anticancer drugs.
Stichworte
antibacterial activity; cytotoxicity activity; microwave irradiation; molecular docking; Schiff base; thermal synthesis
Erscheinungsjahr
2017
Zeitschriftentitel
Zeitschrift für Naturforschung C
Band
72
Ausgabe
11-12
Seite(n)
467-475
ISSN
0939-5075
eISSN
1865-7125
Page URI
https://pub.uni-bielefeld.de/record/2916440

Zitieren

Halawa AH, Abd El-Gilil SM, Bedair AH, et al. Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety. Zeitschrift für Naturforschung C. 2017;72(11-12):467-475.
Halawa, A. H., Abd El-Gilil, S. M., Bedair, A. H., Shaaban, M., Frese, M., Sewald, N., Eliwa, E. M., et al. (2017). Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety. Zeitschrift für Naturforschung C, 72(11-12), 467-475. doi:10.1515/znc-2017-0025
Halawa, Ahmed H., Abd El-Gilil, Shimaa Mohamed, Bedair, Ahmed H., Shaaban, Mohamed, Frese, Marcel, Sewald, Norbert, Eliwa, Essam M., and El-Agrody, Ahmed M. 2017. “Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety”. Zeitschrift für Naturforschung C 72 (11-12): 467-475.
Halawa, A. H., Abd El-Gilil, S. M., Bedair, A. H., Shaaban, M., Frese, M., Sewald, N., Eliwa, E. M., and El-Agrody, A. M. (2017). Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety. Zeitschrift für Naturforschung C 72, 467-475.
Halawa, A.H., et al., 2017. Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety. Zeitschrift für Naturforschung C, 72(11-12), p 467-475.
A.H. Halawa, et al., “Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety”, Zeitschrift für Naturforschung C, vol. 72, 2017, pp. 467-475.
Halawa, A.H., Abd El-Gilil, S.M., Bedair, A.H., Shaaban, M., Frese, M., Sewald, N., Eliwa, E.M., El-Agrody, A.M.: Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety. Zeitschrift für Naturforschung C. 72, 467-475 (2017).
Halawa, Ahmed H., Abd El-Gilil, Shimaa Mohamed, Bedair, Ahmed H., Shaaban, Mohamed, Frese, Marcel, Sewald, Norbert, Eliwa, Essam M., and El-Agrody, Ahmed M. “Synthesis, biological activity and molecular modeling study of new Schiff bases incorporated with indole moiety”. Zeitschrift für Naturforschung C 72.11-12 (2017): 467-475.

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