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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

SCImago Journal Rank (SJR) 2018: 0.263
Source Normalized Impact per Paper (SNIP) 2018: 0.505

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1865-7117
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Volume 72, Issue 10

Issues

Synthesis of unexpected novel bis-coumarin derivatives via three component reactions of 4-hydroxycoumarin, aldehydes and cyclic secondary amines. Conformation in the solid state and pharmacological evaluation

Fatma A. El-Samahy
  • Corresponding author
  • Department of Green Chemistry, Chemical Industries Research Division, National Research Centre, El Buhouth St., P.O. 12622, Dokki, Giza, Egypt
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  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Hayam A. Abd El Salam
  • Department of Green Chemistry, Chemical Industries Research Division, National Research Centre, El Buhouth St., P.O. 12622, Dokki, Giza, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Naglaa F. El-Sayed
  • Department of Organometallic and Organometalloid, Chemical Industries Research Division, National Research Centre, El Buhouth St., P.O. 12622, Dokki, Giza, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Elsayed M. Shalaby
  • X-Ray Crystallography Laboratory, Solid State Physics Department, Physics Division, National Research Centre, El Buhouth St., P.O. 12622, Dokki, Giza, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Mahmoud F. Dondeti
  • Molecular Biology Department, Genetic Engineering and Biotechnology Research Division, National Research Centre, El Buhouth St., P.O. 12622, Dokki, Giza, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2017-09-29 | DOI: https://doi.org/10.1515/znb-2017-0066

Abstract

A series of unexpected bis-coumarins have been synthesized by multicomponent reactions of 4-hydroxycoumarin, aldehydes, and cyclic secondary amines in ethanol at room temperature. The chemical structures of new compounds were identified by 1H, 13C NMR, and mass spectrometry. Furthermore, the molecular structure of the solid-state adduct of 3,3′-[(4-methoxyphenyl)-methylene]bis(4-hydroxy-2H-chromen-2-one) with morpholine (1:1) has been confirmed by single-crystal X-ray diffraction. The cytotoxicity of the new coumarin derivatives against MCF7 breast cancer cells was evaluated. A docking study of the new products was carried out to assess the molecular affinity between the tested compound and Topoisomerase IIa.

Keywords: aldehydes; cyclic secondary amines; cytotoxicity; docking; 4-hydroxycoumarin; multicomponent reactions; single crystal X-ray diffraction

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About the article

Received: 2017-04-13

Accepted: 2017-06-22

Published Online: 2017-09-29

Published in Print: 2017-09-26


Citation Information: Zeitschrift für Naturforschung B, Volume 72, Issue 10, Pages 705–716, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2017-0066.

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