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Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

Journal Article


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Abstract


  • Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine.

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Sastraruji, Thanapat (external author)
  •   Ung, Alison T. (external author)
  •   Griffith, Renate (external author)
  •   Jatisatienr, Araya (external author)
  •   Pyne, Stephen

Publication Date


  • 2012

Citation


  • Sastraruji, K., Sastraruji, T., Ung, A. T., Griffith, R., Jatisatienr, A. & Pyne, S. G. (2012). Synthesis of stemofoline analogues as acetylcholinesterase inhibitors. Tetrahedron, 68 (35), 7103-7115.

Scopus Eid


  • 2-s2.0-84863853821

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2210&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1143

Number Of Pages


  • 12

Start Page


  • 7103

End Page


  • 7115

Volume


  • 68

Issue


  • 35

Abstract


  • Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine.

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Sastraruji, Thanapat (external author)
  •   Ung, Alison T. (external author)
  •   Griffith, Renate (external author)
  •   Jatisatienr, Araya (external author)
  •   Pyne, Stephen

Publication Date


  • 2012

Citation


  • Sastraruji, K., Sastraruji, T., Ung, A. T., Griffith, R., Jatisatienr, A. & Pyne, S. G. (2012). Synthesis of stemofoline analogues as acetylcholinesterase inhibitors. Tetrahedron, 68 (35), 7103-7115.

Scopus Eid


  • 2-s2.0-84863853821

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2210&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1143

Number Of Pages


  • 12

Start Page


  • 7103

End Page


  • 7115

Volume


  • 68

Issue


  • 35