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

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).

Keywords:

• Multicaulin
• miltirone
• synthesis
• antituberculosis

Acknowledgements

The synthetic part of this article is a part of PhD dissertation of Serdar Burmaoğlu. We thank The Scientific and Technological Research Council of Turkey (Tubitak, grant number: 108T115) for financial support. We thank Dr. Oztekin Algul (Mersin University) for encouragement and critical reading for the manuscript. Hasan Seçen thanks Leslie Demir for her critical reading of this article.

Disclosure statement

The authors confirm that this article content has no conflict of interest.

Additional information

Funding

We thank The Scientific and Technological Research Council of Turkey (Tubitak, grant number: 108T115) for financial support.