A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents

Ang Chee Wei, Mohamed Ashraf Ali, Yeong Keng Yoon, Rusli Ismail, Tan Soo Choon, Raju Suresh Kumar

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41 Citations (Scopus)

Abstract

A series of fourteen dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions and were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv in HTS (High Throughput Screen). Most of the compounds showed moderate to good activity with MIC of less than 20 μM. Compound 4′-(4-bromophenyl)-1′- methyldispiro[acenaphthylene-1,2′-pyrrolidine-3′,2″-indane]-2, 1″(1H)-dione (4c) was found to be the most active with MIC of 12.50 μM.

Original languageEnglish
Pages (from-to)1383-1386
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number5
DOIs
Publication statusPublished - 1 Mar 2013
Externally publishedYes

Keywords

  • [3+2]-Cycloaddition
  • Antimycobacterial activity
  • Azomethine ylide
  • Dispiroheterocycle
  • Intermolecular

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