Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

Shambhu Nath Singh, Sridhar Regati, Abir Kumar Paul, Mohosin Layek, Sarva Jayaprakash, K. Venkateshwara Reddy, Girdhar Singh Deora, Soumita Mukherjee, Manojit Pal

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Abstract

CuI facilitated three-component reaction of isatin derivatives, l-proline and terminal alkynes containing an amide or ester functional group. The multi-component reaction (MCR) afforded a faster and practical synthesis of spirooxindole derivatives. A range of novel spirooxindoles were synthesized by using this straightforward and one-pot efficient methodology. A representative compound showed significant inhibition of PDE4B enzyme in vitro and good interactions with this protein in silico.

Original languageEnglish
Pages (from-to)5448-5452
Number of pages5
JournalTetrahedron Letters
Volume54
Issue number40
DOIs
Publication statusPublished - 2 Oct 2013
Externally publishedYes

Keywords

  • CuI
  • MCR
  • PDE4B
  • Spirooxindole

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