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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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1865-7117
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Volume 72, Issue 9

Issues

Synthesis and biological activities of new bis-indole derivatives via microwave irradiation

Ahmed H. Halawa / Ahmed H. Bedair / Ahmed M. El-Agrody / Essam M. Eliwa
  • Chemistry Department, Faculty of Science, Al-Azhar University, 11884 Nasr City, Cairo, Egypt
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
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/ Marcel Frese
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
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/ Norbert Sewald
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
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/ Mohamed Shaaban
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
  • Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, Dokki-Cairo 12622, Egypt
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Published Online: 2017-08-19 | DOI: https://doi.org/10.1515/znb-2017-0039

Abstract

Three new series of bis-indole derivatives were synthesized based on p-phenylenediamine (2–4, 5 and 6) and 4,4′-ethylenedianiline moieties (7–9) using facile and efficient condensation of three positional isomeric indole-carboxaldehyde derivatives (1a–c) with bifunctional amines upon microwave irradiation. The symmetric dimeric indole derivatives 2–4 as well as non-symmetric analogues 5 and 6 were obtained by in situ condensation of the respective positional 3-, 2- and 5-isomeric indole-carboxaldehydes with p-phenylenediamine, while compounds 7–9 resulted from respective condensation based on 4,4′-ethylenedianiline. Structures of the obtained compounds were deduced by advanced spectroscopic methods (1H NMR, 13C NMR and MS). In agar diffusion assay, derivative 6 showed moderate antibacterial activity against various Gram positive and negative bacteria, while derivative 7 displayed moderate activity against several Gram positive bacteria. However, in Resazurin assay employing the human cervix carcinoma cell line (KB-3-1), derivatives 2–9 turned out to be inactive.

This article offers supplementary material which is provided at the end of the article.

Keywords: antibacterial activity; bis-indole derivatives; cytotoxicity; microwave irradiation

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About the article

Received: 2017-02-08

Accepted: 2017-06-02

Published Online: 2017-08-19

Published in Print: 2017-09-26


Citation Information: Zeitschrift für Naturforschung B, Volume 72, Issue 9, Pages 639–646, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2017-0039.

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©2017 Walter de Gruyter GmbH, Berlin/Boston. Copyright Clearance Center

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