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
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
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.
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.

36 References

Daten bereitgestellt von Europe PubMed Central.

Tetrathiafulvalene-based group XV ligands: synthesis, coordination chemistry and radical cation salts
AUTHOR UNKNOWN, Coor Chem Rev 253(), 2009
Medicinal chemistry and the molecular operating environment (MOE): application of QSAR and molecular docking to drug discovery
AUTHOR UNKNOWN, Curr Topics Med Chem 8(), 2008
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
Shaaban M, Maskey RP, Wagner-Dobler I, Laatsch H., J. Nat. Prod. 65(11), 2002
PMID: 12444694
Approaches for the synthesis of functionalized cryptophycins.
Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N., J. Org. Chem. 75(20), 2010
PMID: 20857920

AUTHOR UNKNOWN, 2011
The use of the Gail model, body mass index and SNPs to predict breast cancer among women with abnormal (BI-RADS 4) mammograms.
McCarthy AM, Keller B, Kontos D, Boghossian L, McGuire E, Bristol M, Chen J, Domchek S, Armstrong K., Breast Cancer Res. 17(), 2015
PMID: 25567532
Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives.
El-Sawy ER, Bassyouni FA, Abu-Bakr SH, Rady HM, Abdlla MM., Acta Pharm 60(1), 2010
PMID: 20228041
Dialiumoside, an Olean-18-ene Triterpenoid from Dialium excelsum
AUTHOR UNKNOWN, Z Naturforsch 66b(), 2011
Synthesis and evaluation of 3-aroylindoles as anticancer agents: metabolite approach.
Wu YS, Coumar MS, Chang JY, Sun HY, Kuo FM, Kuo CC, Chen YJ, Chang CY, Hsiao CL, Liou JP, Chen CP, Yao HT, Chiang YK, Tan UK, Chen CT, Chu CY, Wu SY, Yeh TK, Lin CY, Hsieh HP., J. Med. Chem. 52(15), 2009
PMID: 19586033
Polymer-supported Schiff base complexes in oxidation reactions
AUTHOR UNKNOWN, Coor Chem Rev 253(), 2009
Chemical genetics-based discovery of indole derivatives as HCV NS5B polymerase inhibitors.
Jin G, Lee S, Choi M, Son S, Kim GW, Oh JW, Lee C, Lee K., Eur J Med Chem 75(), 2014
PMID: 24561671
Interplay between MMP-8 and TGF-β1 and its role in regulation of epithelial to mesenchymal transition in hepatocellular carcinoma
AUTHOR UNKNOWN, Transl Cancer Res 5(), 2016
Marine natural products.
Blunt JW, Copp BR, Munro MH, Northcote PT, Prinsep MR., Nat Prod Rep 28(2), 2010
PMID: 21152619
Biological properties of Schiff bases and azo derivatives of phenols
AUTHOR UNKNOWN, Curr Org Chem 13(), 2009
Benhamycin, novel alkaloid from terrestrial Streptomyces sp.
Shaaban M, Abdel-Aziz MS., Nat. Prod. Res. 21(13), 2007
PMID: 17987502
Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.
Sugiyama Y, Ito Y, Suzuki M, Hirota A., J. Nat. Prod. 72(11), 2009
PMID: 19943625
A novel phthalocyanine conjugated with four salicylideneimino complexes: photophysics and fluorescence quenching studies
AUTHOR UNKNOWN, Dyes Pigments 95(), 2012
Monoindole alkaloids from a marine sponge Spongosorites sp.
Bao B, Zhang P, Lee Y, Hong J, Lee CO, Jung JH., Mar Drugs 5(2), 2007
PMID: 18463722
Synthesis, cytotoxic, pro-apoptotic evaluation and molecular docking study of some new N-substituted sulphonyl-3-indolyl heterocycles
AUTHOR UNKNOWN, Egypt Pharm J 14(), 2015
Indole-based analogs of melatonin: in vitro antioxidant and cytoprotective activities.
Mor M, Silva C, Vacondio F, Plazzi PV, Bertoni S, Spadoni G, Diamantini G, Bedini A, Tarzia G, Zusso M, Franceschini D, Giusti P., J. Pineal Res. 36(2), 2004
PMID: 14962060
Tumor- and organ-dependent infiltration by myeloid-derived suppressor cells.
Younos I, Donkor M, Hoke T, Dafferner A, Samson H, Westphal S, Talmadge J., Int. Immunopharmacol. 11(7), 2011
PMID: 21376153
Synthesis, antimicrobial and anti-cancer activities of some new N-ethyl, N-benzyl and N-benzoyl-3-indolyl heterocycles.
El-Sawy ER, Mandour AH, Mahmoud K, Islam IE, Abo-Salem HM., Acta Pharm 62(2), 2012
PMID: 22750815
InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives.
Lakshmi NV, Thirumurugan P, Noorulla KM, Perumal PT., Bioorg. Med. Chem. Lett. 20(17), 2010
PMID: 20675130
[(2-Phenylindol-3-yl) methylene] propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G(2)/M phase and apoptosis
AUTHOR UNKNOWN, Bioorgan Med Chem 15(), 2007
Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl] thiosemicarbazide
AUTHOR UNKNOWN, Eur J Pharma Sci 9(), 1999
Antioxidant activity of unexplored indole derivatives: synthesis and screening.
Estevao MS, Carvalho LC, Ribeiro D, Couto D, Freitas M, Gomes A, Ferreira LM, Fernandes E, Marques MM., Eur J Med Chem 45(11), 2010
PMID: 20727623
Synthesis, antimicrobial and anticancer activities of some new N-methylsulphonyl and N-benzenesulphonyl-3-indolyl heterocycles
AUTHOR UNKNOWN, Arabian J Chem 6(), 2013
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 28525356
PubMed | Europe PMC

Suchen in

Google Scholar