Antimycobacterial activity: A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines

Ang Chee Wei, Mohamed Ashraf Ali, Yeong Keng Yoon, Rusli Ismail, Tan Soo Choon, Raju Suresh Kumar, Natarajan Arumugam, Abdulrahman I. Almansour, Hasnah Osman

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Abstract

A series of twelve dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis strains using agar dilution method, four of them showed good activity with MIC of less than 1 μM. Compound 4′-[5-(4-fluorophenyl)pyridin-3-yl]-1′-methyldispiro[indan-2, 2′ pyrrolidine-3′,2″-indan]-1,3,1″-trione (4b) was found to be the most active with MIC of 0.1215 and 5.121 μM, respectively.

Original languageEnglish
Pages (from-to)4930-4933
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number15
DOIs
Publication statusPublished - 1 Aug 2012
Externally publishedYes

Keywords

  • Antimycobacterial activity
  • Azomethineylide
  • Dispiropyrrolidines
  • Indanone
  • Intermolecular 1,3-dipolar cycloaddition

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