Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents

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Abstract

A series of novel spiro[indole-thiazolidine]spiro[indole-pyran] derivatives were synthesized from N-(bromoalkyl)indol-2,3-diones via monospiro-bisindole intermediates; the two indole nuclei being connected via N-(CH(2))(n)-N linker. Synthesized compounds were evaluated for their antimicrobial activities in vitro against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Staphylococcus epidermis), four Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, and Klebsiella pneumonia) as well as four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, and Candida albicans) using Cup plate method. Bis spiro-indoles exhibited stronger antibacterial and antifungal efficiency than their corresponding mono spiro-indoles. Compound 10e, the most active derivative was shown to inhibit the growth of all bacterial strains and two fungal strains (A. niger and C. albicans).

Original languageEnglish (US)
Pages (from-to)5465-9
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number18
DOIs
StatePublished - Sep 15 2011

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Keywords

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Bacteria
  • Chemistry Techniques, Synthetic
  • Drug Design
  • Fungi
  • Indoles
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrans
  • Spiro Compounds
  • Stereoisomerism
  • Thiazolidines
  • Journal Article
  • Research Support, Non-U.S. Gov't

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