Catalysis Letters

, Volume 144, Issue 12, pp 2091–2106 | Cite as

Catalyst Promoted Synthesis, Computational and Enzyme Inhibition Studies of Coumarin Esters

  • Mehtab Parveen
  • Faheem Ahmad
  • Ali Mohammed Malla
  • Mahboob Alam
  • Dong-Ung Lee
Article
First Online:
Received:
Accepted:

Abstract

In the present study, a new series of ester analogues of substituted coumarin-3-carboxylic acids were synthesized which were typically accessed via a facile esterification reaction between propargyl alcohol and appropriately substituted coumarin-3-carboxylic acids (1–5). This new environmentally benign solid acid catalyst catalyzed, synthetic eco-friendly approach resulted in a noteworthy progress in synthetic efficiency (89–94 % yield), high purity, operational simplicity, mild reaction conditions, cleaner reaction profiles, recyclability of the catalyst and minimizing the production of chemical wastes without using highly toxic reagents for the synthesis. The molecular structure of compound 6 was authenticated by single crystal X-ray crystallographic analysis. The structure and morphology of the catalyst has been established on the basis of FT-IR, scanning electron microscopy–energy dispersion X-ray spectrometry and transmission electron microscopy. The promising bioactive score against enzymatic inhibition prompted us to carry out acetylcholinesterase inhibition screening of the synthesized compounds (6–10). A computer-aided molecular docking study was carried out to validate the specific binding mode of the newly synthesized compounds into the active site of receptor to bear out the specific binding modes of the compounds.

Graphical Abstract

Keywords

Synthesis Chromene-3-carboxylate Catalyst Silica-sulfuric acid X-ray AChE inhibition 
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Notes

Acknowledgments

Authors thank the Chairman, Department of Chemistry, A.M.U, Aligarh, for providing necessary research facilities, University Sophisticated Instrument Facility (USIF), AMU, Aligarh for providing SEM–EDX facilities, SAIF Panjab University Chandigarh for TEM analysis and spectral studies, Division of Bioscience, Dongguk University, Gyeongju, South Korea is acknowledged for bioassay and X-ray analysis. UGC is also gratefully acknowledged for research fellowship to Faheem Ahmad and Ali Mohammed Malla.

Supplementary material

10562_2014_1381_MOESM1_ESM.docx (4.6 mb)
Supplementary material 1 (DOCX 4736 kb)

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Mehtab Parveen
    • 1
  • Faheem Ahmad
    • 1
  • Ali Mohammed Malla
    • 1
  • Mahboob Alam
    • 2
  • Dong-Ung Lee
    • 2
  1. 1.Department of ChemistryAligarh Muslim UniversityAligarhIndia
  2. 2.Division of BioscienceDongguk UniversityGyeongjuRepublic of Korea

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