3-(Phenethylamino)demethyl(oxy)aaptamine as an anti-dormant mycobacterial substance: Isolation, evaluation and total synthesis

Yuji Sumii, Naoyuki Kotoku, Chisu Han, Kentaro Kamiya, Andi Setiawan, Catherine Vilchèze, William R. Jacobs, Masayoshi Arai

Research output: Contribution to journalArticlepeer-review

Abstract

3-(Phenethylamino)demethyl(oxy)aaptamine (1) was re-discovered from the marine sponge of Aaptos sp. as an anti-dormant mycobacterial substance through the bioassay-guided separation. Compound 1 showed potent anti-microbial activity against Mycobacterium bovis BCG with a minimum inhibitory concentration of 0.75 µg/mL under both aerobic conditions and hypoxic conditions inducing dormant state. Compound 1 was also effective against pathogenic M. tuberculosis strains including clinical multidrug-resistant strains. Furthermore, the successful total syntheses of 1 and its analog 3-aminodemethyl(oxy)aaptamine (2) afford sufficient quantities for further biological studies.

Original languageEnglish (US)
Article number151924
JournalTetrahedron Letters
Volume61
Issue number22
DOIs
StatePublished - May 28 2020

Keywords

  • Aaptamine derivative
  • Antimicrobial
  • Dormant
  • Tuberculosis
  • ZIWLGKRCCRFXQK-UHFFFAOYSA-N

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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