Medicinal Chemistry Research

, Volume 26, Issue 12, pp 3247–3261 | Cite as

Molecular docking and glucosidase inhibition studies of novel N-arylthiazole-2-amines and Ethyl 2-[aryl(thiazol-2-yl)amino]acetates

  • Ayesha Babar
  • Muhammad Yar
  • Hamadeh Tarazi
  • Vera Duarte
  • Mohammed B. Alshammari
  • Mazhar Amjad Gilani
  • Haffsah Iqbal
  • Munawwar Ali Munawwar
  • Maria J. Alves
  • Ather Farooq Khan
Original Research
  • 267 Downloads

Abstract

This study describes an efficient synthesis of a series of novel ethyl 2-[aryl(thiazol-2-yl)amino]acetates (4al) from N-arylthiazole-2-amines (3al). The reaction conditions were optimized and the best results were obtained when ethyl chloroacetate was used as alkylating agent and NaH as base in THF. α-glucosidase and β-glucosidase inhibition activities of N-arylthiazole-2-amines (3al) and ethyl 2-[aryl(thiazol-2-yl)amino]acetates (4al) were determined, which revealed that most of the compounds showed high percentage inhibition towards the enzymes. Among the synthesized compounds, 4e appeared to have the highest inhibition towards α-glucosidase having IC50 value of 150.4 ± 1.9 μM which was almost two folds as compared to acarbose (336.9 ± 9.0 μM) taken as standard. Molecular docking of the compounds 3g, 3f, 4a, and 4e was also performed which showed their bonding modes to the enzyme’s active sites via amino and acetate groups, respectively.

keywords

α- and β-glucosidase inhibition Thiazoles Molecular docking 

Notes

Acknowledgements

A.F. Khan is thankful to Higher Education Commission, Pakistan for providing funding under NRPU project No. 1690 for this research.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Ayesha Babar
    • 1
    • 2
  • Muhammad Yar
    • 1
  • Hamadeh Tarazi
    • 3
  • Vera Duarte
    • 4
  • Mohammed B. Alshammari
    • 5
  • Mazhar Amjad Gilani
    • 5
    • 6
  • Haffsah Iqbal
    • 1
  • Munawwar Ali Munawwar
    • 2
  • Maria J. Alves
    • 4
  • Ather Farooq Khan
    • 1
  1. 1.Interdisciplinary Research Centre in Biomedical MaterialsCOMSATS Institute of Information TechnologyLahorePakistan
  2. 2.Institute of ChemistryUniversity of the PunjabLahorePakistan
  3. 3.Department of Medicinal Chemistry, College of PharmacyUniversity of SharjahSharjahUAE
  4. 4.Chemistry Department, College of Sciences and HumanitiesPrince Sattam bin Abdulaziz UniversityAl-KharijSaudi Arabia
  5. 5.Department of ChemistryUniversity of Minho, Campus de GualtarBragaPortugal
  6. 6.Department of Chemical EngineeringCOMSATS Institute of Information TechnologyLahorePakistan

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