Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents

BURMAOĞLU S., Secinti H., Mozioglu E., Goren A. C., Altundas R., SEÇEN H.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.32, no.1, pp.878-884, 2017 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 32 Issue: 1
  • Publication Date: 2017
  • Doi Number: 10.1080/14756366.2017.1337758
  • Journal Name: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.878-884
  • Keywords: Multicaulin, miltirone, synthesis, antituberculosis, MYCOBACTERIUM-TUBERCULOSIS, NATURAL-PRODUCTS, DRUG DISCOVERY, ESSENTIAL OILS, LEADS
  • Yozgat Bozok University Affiliated: No

Abstract

Four multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9, 10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9, 10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions. The best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol (11).